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Holiday Rentals and Villas in Orleans, MA

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    Travellers to Orleans are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 26
    5 of 5 stars (2) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    1 / 16
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This 3 Bedroom 2.5 bath retreat with Central AC is hidden away down a semi private drive in East Orleans. It has large sliding glass doors down one side of the home off the living room offering lots of light. Mid century modern decor fills this clean lined living space. Passive solar compliments... View all property information
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    Orleans, Cape Cod
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This is a newer three bedroom two and a half bath home with a large kitchen and open dining and living area. There are three large bedrooms. One on the first floor with a queen bed and its own full bathroom and two more bedrooms on the second floor with a full bath, one with two twins and one with... View all property information
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    Orleans, Cape Cod
    1 / 18
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Terrace
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    About this property
    *If you can't find the dates available that you are looking for, we also have a second studio you may be interested in. Send us an inquiry and we will try to help you find the dates you want.* Beach Rose is a studio in “Holly Tree Cottages” available by world-renowned Nauset Beach. It offers high... View all property information
    Location Information
    Orleans, Cape Cod
    5 of 5 stars Reviewed 1 week ago
    We wanted an affordable quiet place near a beach. The studio was neat, clean, right near wonderful Nauset Beach and it had everything except the kitchen sink. It was just what we...
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    1 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This beautiful Cape Cod home sits on Barley Neck, which is small peninsula just a few minutes drive to Nauset Beach. Beach sticker for parking is included in your rental! It is surrounded by Meeting House Pond and Little Pleasant Bay. This area is harbored from the Atlantic Ocean by Pochet Island.... View all property information
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    Orleans, Cape Cod
    1 / 6
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Lovely Summer Rental in East Orleans. Approximently 0.5 miles from Nauset Beach. This apartment will sleep 4. One seperate bedroom with queen bed. Bathroom and shower. Murphy bed available.in sitting area. Comfortable sitting area with Direct TV, WiFi, washer and dryer, microwave among the... View all property information
    Location Information
    Orleans, Cape Cod
    5 of 5 stars Reviewed 27 August 2015
    Had a wonderful week with our family at this beautiful apartment. It is exactly like the photos! Clean, quiet and relaxing! Would definitely return! The owners live on the...
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    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This delightful, newly renovated and furnished cottage is situated on 1.5 acres of land and offers peace and quiet - right on Pilgrim Lake in Orleans! Central A/C has been added for the summer season!!! This two bedroom, one bath cottage is perfect for a couple or small family of four. Take in the... View all property information
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    Orleans, Cape Cod
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Secure Parking
    • Central Heating
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    • Waterfront
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    • x
    About this property
    Classic Nauset Heights 3 Bedroom home sitting directly on the bluff with magnificent views of Nauset Beach, the Atlantic Ocean, Nauset Marsh, Coast Guard Light, and Fort Hill. Short walk to bay and ocean beaches. Vintage cottage character in unbelievable location. Great value for view. Full... View all property information
    Location Information
    Orleans, Cape Cod
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    1 / 18
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Washer
    • Waterfront
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    • x
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    About this property
    Waterfront Beach Cottage, just bring your boat! You will love the deep water access right in your back yard. Enjoy Cape Cod at its best! Swim, kayak, fish and clam at your doorstep. This professionally decorated beachfront cottage is sure to please. Home offers gorgeous Kitchen, 2 full baths, 3... View all property information
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    Orleans, Cape Cod
    1 / 14
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Located in desirable East Orleans, Nauset Heights, this beautiful 3 bedroom, 1 bath home is a walk to the Outer North Nauset beach by way of Nauset Heights Association access & a great salt water inlet off the ocean. Private Nauset beach access is just 3/10ths of a mile away, Priscilla Landing... View all property information
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    Orleans, Cape Cod
    1 / 7
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This small two bedroom home has all the quiet charm that you would expect for your cape cod vacation. Perfect for a couple or a small family, this home offers relaxation. - All reservations have a $60 reservation fee and a refundable security deposit. - Additional amenities include: coffee maker,... View all property information
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    Orleans, Cape Cod
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Washer
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    • Grill
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    About this property
    Chill out (now with central A/C!) and relax at this wonderful waterfront retreat located in Mayflower Point. This charming cottage offers wonderful views of Lonnie's Pond and Kent's Point and has its own path to Lonnie's River leading out to Pleasant Bay. Perfect for boating or kayaking. Many... View all property information
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    Orleans, Cape Cod
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This Pet friendly home is located just 0.8 miles from Nauset Beach. Enter into a charming, warm home that offers two spacious living areas. One is a bright great room with cathedral ceilings, sectional seating, big screen t.v and game table. Head into the living room where you will find a cozy... View all property information
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    Orleans, Cape Cod
    1 / 23
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Patio
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    About this property
    *If you can't find the dates available that you are looking for, we also have a second studio you may be interested in. Send us an inquiry and we will try to help you find the dates you want.* Sea Wind is a studio in “Holly Tree Cottages” available by world-renowned Nauset Beach. It offers high... View all property information
    Location Information
    Orleans, Cape Cod
    4 of 5 stars Reviewed 11 July 2016
    Short walk to Nauset beach. Short bike ride to shops, ponds. Unit could use some care but is comfortable and well appointed for relaxed studio stay and a great value for the...
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    1 / 18
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Wi-Fi
    • Satellite TV
    • Terrace
    • Grill
    • Secure Parking
    • Balcony
    • Waterfront
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Classic Nauset Heights home sitting directly on the bluff with magnificent views of Nauset Beach, the Atlantic Ocean and Nauset Marsh. Short walk to bay and ocean beaches. Vintage, rustic cottage character in unbelievable location. Great value for view. Wooden farmhouse style floors throughout... View all property information
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    Orleans, Cape Cod
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Spotless home in a lovely quiet setting near the bike path. There are two living spaces and a first floor laundry and half bath. The first floor bedroom has a queen size bed. On the second floor there are two bedrooms with a queen bed and two twin beds and a full bath. Large two level deck. There... View all property information
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    Orleans, Cape Cod
    1 / 30
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Pet-friendly
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    • ?
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    • ?
    About this property
    Cosy, welcoming home in South Eastham. Our traditional Cape Cod house features 4 bedrooms, 2 baths, and a fully finished basement with easy access to beaches, the Cape Cod Bike Trail, shopping and restaurants. Three bedrooms and the living room have window A/C units. We are on a quiet wooded lane,... View all property information
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    Orleans, Cape Cod
    1 / 31
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    This recently remodeled 3 bedroom 1.5 miles from Nauset Beach offers lots of open living space inside and out. 3 living rooms and a lower level entertainment area give this home room for the whole family to gather together or spread out for different activities. The outside lawns are expansive as... View all property information
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    Orleans, Cape Cod
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    1 / 27
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Beautiful Open Layout with updated furnishings on Nauset Heights! Walk to Nauset Beach. Unique extras like large outdoor shower, original artwork, and private setting. See reviews and latest availability and pricing on our site: nausetrental For 2015: A/C in all Bedrooms, All new bedding,... View all property information
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    Orleans, Cape Cod
    1 / 10
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • ?
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    • ?
    About this property
    Adorable updated two bedroom cottage with a bright screened in porch, outdoor shower and A/C units. Located in the Pine Tree Cottage colony. The first bedroom has a full bedroom and the second has two twins and there is a full bathroom with a shower. This cottage is perfect for a family of four or... View all property information
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    Orleans, Cape Cod
    1 / 11
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    • Pet-friendly
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    • x
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    • x
    About this property
    REMAINING WEEKS - $150 DISCOUNT! This charming and pristine contemporary ranch, nestled in a private wooded paradise-Mayflower Point, is minutes by foot to private salt and fresh water accesses for boating, swimming, or fishing. Launch a kayak at ''The River'', leading to Pleasant Bay and the outer... View all property information
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    Orleans, Cape Cod
    1 / 21
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    Crystal Lake Waterfront! Enjoy fresh water swimming right outside your door! This wonderful, private spot is ideal for the extended family offering 5 bedrooms plus an office/den, including an incredibly spacious master bedroom suite and two other bedrooms that open out onto a screened porch that... View all property information
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    Orleans, Cape Cod
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Lovely three bedroom contemporary Cape with an open floor plan located in a private cul de sac neighborhood. Features wireless internet, deck and private outdoor shower and is near the bike trail. Two bedrooms are on the first floor. One with a trundle bed and the other with two twins. Upstairs... View all property information
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    Orleans, Cape Cod
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Wonderful home in very private East Orleans setting! Screened-in porch off the well-equipped kitchen area to enjoy all our summer meals. There is even a large deck off kitchen for grilling and relaxing. There are (3) bedrooms on first level including (1) king bedroom suite, and also (2) Queens... View all property information
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    Orleans, Cape Cod
    1 / 17
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Stunning Carriage House with Ocean Views in Nauset Heights. This home has an authentic feel of a post and beam barn. Superbly appointed with sliding barn doors, authentic wide pine floors and an enormous fieldstone fireplace. Home offers an amazing kitchen, one bedroom plus open loft and a view... View all property information
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    Orleans, Cape Cod
    1 / 17
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Skaket Beach at just 1000 ft!! This gorgeous Orleans vacation rental home is located in the perfect spot for you to enjoy Cape Cod. At this lovely home you will be just 2/10ths of a mile from beautiful private access to Skaket Beach in Orleans on Cape Cod Bay. This home is located on an old Cape... View all property information
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    Orleans, Cape Cod
    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    This 2 bedroom Orleans cottage is light and bright and offers close proximity to Skaket Beach! Located in a residential neighborhood, it features two bedrooms and two full baths, sleeping up to 5 comfortably. There is a fully equipped kitchen with eat in dining area, cozy living area with flat... View all property information
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    Orleans, Cape Cod
    1 / 21
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Walk to Skaket Beach, Orleans Center & Bike Path, Renovated, A/C in all rooms & WIFI - Mere steps to the Cape Cod Rail Trail and under a mile to Skaket Beach and the shops and restaurants on Main Street in Orleans. This charming, renovated, antique home is the perfect place to spend your Cape... View all property information
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    Orleans, Cape Cod
    1 / 21
    5 of 5 stars (5) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Priscilla Landing is on the Nauset Estuary and has private pathways to the Atlantic. The first floor has 3 bedrooms. One room has Queen sized bed with a private bath. Second room as 2 twins also with a private bath. The Master suite has a King sized bed, Private Bath with walk-in shower and a... View all property information
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    Orleans, Cape Cod
    1 / 15
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Overlooking the salt waters of Mill Pond and located in grand Ocean Harbor Estates! The Atlantic Ocean is just beyond this amazing waterway. Only 2 miles from Nauset Beach and 1.5 miles to East Orleans Village. This property has it all. Views, association dock and tennis court privileges. Open... View all property information
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    Orleans, Cape Cod
    1 / 21
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Skaket Beach at just 2/10ths of a mile, gorgeous marsh views and will be completely completely renovated & newly furnished for 2013! This rental home is perfect for the family. It has a lovely deck area with deck furniture to enjoy the stunning views, central a/c to keep you comfortable, 3... View all property information
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    Orleans, Cape Cod
    1 / 23
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This lovely East Orleans vacation rental home is located apprx. 1 mile to Nauset Beach and apprx. 8/10ths of a mile to East Orleans Village with Joe s Bar n Grill (BNI), Zia s PIzzeria, Sundae School Ice Cream and Nauset Farms Market. This home has 4 bedrooms, 2 bathrooms, a gorgeous outdoor patio... View all property information
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    Orleans, Cape Cod
    1 / 15
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
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    About this property
    Spend time in this classic waterfront getaway know as The 'Boathouse' at 'Topside'. Enjoy water views from every room. You and your guests will feel like you are on your own private boat, sailing the blue water of Pleasant Bay. Swim directly from your steps leading into the water or spend the day... View all property information
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    Orleans, Cape Cod
    1 / 23
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Nauset Beach!! At this lovely East Orleans vacation rental home you can enjoy the best of Cape Cod. This 4 bedroom, 2 bath home has everything you need for a comfortable stay here in East Orleans. There are A/C units, WIFI internet access,, outdoor grill and plenty of outdoor living space. The... View all property information
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    Orleans, Cape Cod
    1 / 21
    4.5 of 5 stars (3) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Contemporary home with private setting just 3/10 mile walk through a private neighborhood association path to Skaket Beach. Back yard overlooks an active cranberry bog! Near the Cape Cod Bike Trail and less than a mile to Rock Harbor fishing fleet. There are 3 decks and a fully screened porch with... View all property information
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    Orleans, Cape Cod
    1 / 13
    5 of 5 stars (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Beautiful and spacious vacation home located in one of the best spots in East Orleans. This home offers 4 bedrooms appointed with gorgeous bedding and 3 1/2 artistically tiled bathrooms. The entire home is decorated with a summer theme of the best that Crate and Barrel has to offer. You can relax... View all property information
    Location Information
    Orleans, Cape Cod
    5 of 5 stars Reviewed 15 June 2015
    This house is beautiful!! I wish I had recorded our reaction when we arrived and entered the home for the first time :). Very Comfortable and spacious great for family and small...
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Terrace
    • Satellite TV
    • Secure Parking
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Layout of Bedrooms: 1st Floor: * Living room with gas fireplace * Dining room / Kitchen / lounge area and dining nook * Master Suite with 1 Queen bed and with private bathroom Full bath/ shower * 1/2 bath 2nd Floor: * Library/office * 2 Twins room and sitting area * Master Bedroom with King... View all property information
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    Orleans, Cape Cod
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    You will find that all your expectations are exceeded in this custom built Cape vacation dream home. The front door opens to an inviting and airy foyer complete with nautical décor and powder room. To the right you enter the large living room with ample seating and flat screen TV with DVD player.... View all property information
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    Orleans, Cape Cod
    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Private Outdoor...
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    • x
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    • x
    About this property
    This exceptional compound is one-of-a-kind with a Main House, Carriage House and private pool. The Main house has a restaurant quality kitchen which will bring out the Iron Chef in you. Ample seating in the dining area with separate bar. Entertaining is easy in the Living Room with HDTV and DVD,... View all property information
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    Orleans, Cape Cod
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    • Balcony
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Savor soothing views of Pleasant Bay, Nauset Bar and Ocean beyond! Gorgeous sun and moon rises too! Swim, fish, shell or relax from private beach and dock - 3 minutes; door to dock. A large, sunny & beautifully maintained home in lovely East Egg affords the space and amenities to insure a fabulous... View all property information
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    Orleans, Cape Cod
    1 / 19
    3.5 of 5 stars (4) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located 1/10 of a mile from the private saltwater beach on Pleasant Bay via an Association path, this multi-level contemporary offers a peaceful retreat on Shoal Pond in South Orleans. The main level is open and bright, with a wonderfully open great room, fireplace, dining area, kitchen, entry way,... View all property information
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    Orleans, Cape Cod
    1 / 13
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Ultimate privacy and Olde Cape Cod charm in one of the most pristine areas of East Orleans. This home is completely renovated, tastefully decorated, and comfortably furnished for your summer enjoyment. Central A/C throughout the home, lots of natural light, extra rooms that ramble with nooks and... View all property information
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    Orleans, Cape Cod
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • ?
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    • x
    About this property
    Located right on the shore of beautiful Town Cove in Orleans. This family home has 3 bedrooms 2 baths and a view of the water which is special. This classic Cape Cod home is one floor living with all 3 bedrooms on the main floor. The master has a Queen with private bath with a walk-in shower, BR2... View all property information
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    Orleans, Cape Cod
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Porch
    • Washer
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    1800s Antique Victorian only 1 mile from the Beach! Front porch rockers and side deck overlook the beautiful yard and gardens. The living room, dining room and family/tv room are very welcoming on the main level. One bedroom with a Queen bed is also located downstairs. Three additional bedrooms... View all property information
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    Orleans, Cape Cod
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Walk to Nauset Beach from this wonderful home. Once part of the historic Mayo Duck Farm and a 2/10 mile walk from beautiful Nauset Beach and the Atlantic Ocean. This home has been completely "refreshed" for the 2014 season including some new furniture, new rugs and curtains, and even a new flat... View all property information
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    Orleans, Cape Cod
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Porch
    • Outdoor Dining Area
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    • ?
    • Smoking allowed
    • x
    About this property
    AT SKAKET BEACH! This charming renovated 1927 Cape has ample room for 6, a master bedroom with a vaulted ceiling and a private half-bath, plus a lovely wraparound porch with hammock. The sunny interior features newly-painted floors, comfy furnishings throughout and excellent amenities, including... View all property information
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    Orleans, Cape Cod
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Child-friendly
    • x
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    • x
    About this property
    This beautiful 4 bedroom East Orleans home is just over a mile to popular Nauset Beach. The exterior of the home boasts a beautiful landscape and large, private driveway. The interior features a large and very open kitchen with beautiful hardwood floors and includes a dining area. Off the dining... View all property information
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    Orleans, Cape Cod
    1 / 14
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Satellite TV
    • DVD Player
    • Air Conditioning
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Water views with dock access out to Meetinghouse pond and Little Pleasant Bay. Absolutely charming two bedroom cottage with water access. This home is part of a 4 building compound on a private yard that abutts private conservation land with views of the river leading to Pleasant Bay. Bring your... View all property information
    Location Information
    Orleans, Cape Cod