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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 / 6
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 30
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    1 / 18
    4 Bedrooms, 1 Bathroom, Sleeps 8 | 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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    About this property
    100 Yards from Water! Its hard to beat the location and value of this charming, well-appointed, 3 bedroom cottage on picturesque Nauset Heights with a short walk to both inland waterways and famous Nauset Beach. Set in a beautiful and relaxing setting - a perfect refuge. 3 Bedrooms. One Queen.... View all property information
    Location Information
    Orleans, Cape Cod
    4 of 5 stars Reviewed 2 weeks ago
    This is the 3rd time we've rented this place. Comfortable, clean and close to the beach. A 10 minute walk to the outer end of Nauset, and minutes to the inlet. Nice little...
    5 of 5 stars Reviewed 20 May 2016
    My family of four (inc. two young children) loved the four nights we spent at this cottage. Nice, well-maintained property in a beautiful, quiet area and only 10 minutes walk to...
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    1 / 31
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    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 / 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 5 days 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 / 29
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
    1 / 26
    5 of 5 stars (2) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Wi-Fi
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    • Waterfront
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    • x
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    About this property
    Classic Nauset Heights! Walk to Nauset Beach & Views of Atlantic Ocean! Unique extras like rain shower, summer reading library, mid-cen artwork, mature gardens and 900 sq ft deck. New Outdoor Shower, A/C in Beds, Beach chairs /wagon provided! 5-minute walk to Nauset Beach, views of the Atlantic... View all property information
    Location Information
    Orleans, Cape Cod
    5 of 5 stars Reviewed 25 May 2016
    Great rental property with fantastic views of Nauset Beach. Very close to main beach and a quick trip into town for anything you may need. The house itself has plenty of space and...
    5 of 5 stars Reviewed 17 May 2016
    Organizing a place to stay for a large group can often be difficult however this was not the case here. Kent and Nicole were always available and responsive through email to...
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    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Grill
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    • Secure Parking
    • Central Heating
    • Porch
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
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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 / 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 / 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
    Location Information
    Orleans, Cape Cod
    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
    Location Information
    Orleans, Cape Cod
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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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
    Location Information
    Orleans, Cape Cod
    1 / 11
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Terrace
    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our home is located in a quiet upscale neighbourhood close to all amenities. Walk to grocery store, downtown shopping, library, tennis courts and town field. Less than a 5 minute drive to ocean and bay. Quick access to highway and all the surrounding Cape towns. Relax and unwind at With the... View all property information
    Location Information
    Orleans, Cape Cod
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Air Conditioning
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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
    Location Information
    Orleans, Cape Cod
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    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
    Location Information
    Orleans, Cape Cod
    1 / 30
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Child-friendly
    • x
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    • Smoking allowed
    • x
    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
    Location Information
    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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    • x
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    • x
    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 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    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
    Location Information
    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
    Location Information
    Orleans, Cape Cod
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    At the end of a private lane lies your secluded vacation retreat on tranquil Pilgrim Lake. Just 60 feet from the decks and living room window is your private lakefront with boat dock for swimming, boating or fishing. The main deck, overlooking the water with comfortable outdoor furniture and gas... View all property information
    Location Information
    Orleans, Cape Cod
    1 / 21
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    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
    Location Information
    Orleans, Cape Cod
    1 / 15
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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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 / 10
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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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
    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 / 22
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Masterfully Renovated across from Pleasant Bay(Linens Included) Peak Summer Weekly Rates: $3,400 - $3,700 This pristine property is located on Orleans Road in Orleans. Every room, every aspect of this newly renovated home is truly something special. The home is brand new in every aspect. Stainless... View all property information
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    Orleans, Cape Cod
    1 / 48
    10 Bedrooms, 8 Bathrooms, Sleeps 24 | Quick View
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    About this property
    Orleans Estate (3 structures) with large heated pool, on Town Cove, Sleeps up to 24 Peak Summer Weeks from $24,500 SEPT/OCT Rentals – Now available, rent the Main House and Carriage House, which sleeps up to 18, for a reduced rate. You will still enjoy the brand new pool area too! Rates range from... View all property information
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    Orleans, Cape Cod
    1 / 24
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
    About this property
    Beach, Kayaks, SUPs on Pristine Orleans Lake! (Pets Considered) Please Note: This home rents Sunday to Sunday in peak summer months Peak Summer Weekly Rates: $4,500 - $4,800 Expansive Waterfront Home on Crystal Lake in the heart of Orleans. Crystal Lake is a pristine fresh water lake located close... View all property information
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    Orleans, Cape Cod
    1 / 24
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
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    • 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 / 32
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Spacious Bay Side Orleans Waterfront Home Next to Skaket Beach PEAK SUMMER WEEKLY RATE: $7,200-$7,500 Situated between Skaket Beach and Rock Harbor, this magnificent home leaves nothing to be desired. Commanding views and direct access to private beach land compliment the seclusion and privacy at... View all property information
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    Orleans, Cape Cod
    1 / 24
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Secluded Cape Cottage, 3-5 Minute Walk to Beach $1,900 PRIME SUMMER WEEKLY RATE It’s possibly one of the best values in Orleans. Located on the Bayside of Orleans, this well-maintained cottage is one of 4 homes on a 25 acre family estate located between Skaket Beach and Rock Harbor on Cape Cod Bay.... View all property information
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    Orleans, Cape Cod
    1 / 47
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Luxurious Orleans Home with Private Salt Pool, Sleeps 10 (linens included) Peak Summer Weekly Rates: $8,500 - $9,000 Located on a large private lot in South Orleans, this luxurious property provides the highest level of amenities and diverse indoor and outdoor living space. With an eclectic... View all property information
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    Orleans, Cape Cod
    1 / 33
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    Sweeping Bay Views, Privacy, Two Full Kitchens(Pets Considered) Peak Summer Weekly Rates: $4,200 - $4,400 This unique vacation home is nestled between Rock Harbor to the east and Skaket beach to the west. The home has its own private boardwalk across the tidal areas. You'll have your feet in the... View all property information
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    Orleans, Cape Cod
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    New and upscale with guest house, walk to Skaket Beach $3,500 - $3,800 prime summer weekly rate. This home is about a 10 minute walk to Skaket Beach or a very short drive. It's less than a mile (0.8 miles) to the bike trail also. You do have distant views of the bay and the property abuts Namskaket... 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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    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 / 35
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    • x
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    • x
    About this property
    Spacious Orleans Home on Crystal Lake Includes Linens and Beach with Kayaks, Canoe & SUP Boards! Please Note: This home rents Sunday to Sunday Peak Summer Weekly Rates: $4,900 This expansive waterfront home is located on Crystal Lake in the heart of Orleans. Kayaks, a canoe and stand-up paddle... View all property information
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    Orleans, Cape Cod
    1 / 41
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Newly remodeled historic home. Heated Pool, Central AC, Sleeps 12, Linens & Towels Included! Peak Summer Weekly Rates: $9,500 This beautiful 1920 Orleans home, newly remodeled and redecorated, exudes Cape Cod charm, retains its original historic character and provides the highest level of modern... View all property information
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    Orleans, Cape Cod
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    About this property
    Large 5 Bedroom with AC on Skaket Beach Please note: This property rents Sunday to Sunday with some exceptions in May-June Here's a great find: a top quality vacation home, located directly on the beach that can comfortably accommodate a guest group up to 10, and is thoroughly and tastefully... View all property information
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    Orleans, Cape Cod
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    • DVD Player
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    • Washer
    • Porch
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    • Pet-friendly
    • Child-friendly
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    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
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Beautiful Pleasant Bay Views, Large upscale home in secluded neighborhood Peak Summer Weekly Rates: $5,400 - $5,900 Nestled in the woods of South Orleans on Pleasant Bay on 6.5 acres, this gorgeous home is a luxurious way to vacation on the lower Cape. The home has over 5000 square feet of living... 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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    • DVD Player
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    • Patio
    • Balcony
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    • Pet-friendly
    • Child-friendly
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    About this property
    First floor master suite and fully equipped separate guest suite make this newer custom Cape an ideal property for two families. The spacious design and top quality appointments in this builders own home assure you a comfortable, relaxing, and memorable vacation you'll truly enjoy. Granite... View all property information
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    Orleans, Cape Cod
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Incredible spot! Expansive Cape cottage on a bluff in Nauset Heights overlooking Nauset Inlet and the Atlantic with a newer upper level deck and a private stairway down to the beach. Casual Olde Cape Cod with pine panelling throughout. The main floor bedrooms consist of a large bedroom with double... View all property information
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    Orleans, Cape Cod
    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Outdoor Dining Area
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    • Pet-friendly
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    • x
    About this property
    New Listing! Bright and spacious ranch located on a wonderful, 1.2 acre level lot off a quiet lane the desirable Barley Neck area of East Orleans. With A/C units in the living area, loft and bedrooms, and brand new finishes and furnishings throughout! Two bedrooms are on the main floor, each with a... 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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    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
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Ocean Views
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful waterfront vacation home with 180 degree unobstructed views of the Frostfish Cove, The River, Jack Knife Point and the mouth Pleasant Bay. This vacation home is about light-filled rooms virtually all with a view of the water, kayaking, canoeing, sailing, fishing and more: a most unique,... View all property information
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    Orleans, Cape Cod
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    • Grill
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    About this property
    Upgraded & upscale near Nauset Beach, Linens Included Peak Summer Weekly Rates: $4,500 - $4,900 This property rents Sunday to Sunday This spacious East Orleans home is located just off Nauset Beach in the desirable Grand View neighborhood. This neighborhood is characterized by rolling lawns,... View all property information
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    Orleans, Cape Cod
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Washer
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    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Parking
    • Grill
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    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
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    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
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Enjoy an expansive layout at this antique 3 bedroom, 3 full bath home featuring a living room, two dens, dining room, large open kitchen and much more! On the first level is a Master Suite with a queen sized bed and full bathroom, with a shower and large soaking tub. Just off the Master Suite is... View all property information
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    Orleans, Cape Cod
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Internet Access
    • Satellite TV
    • Patio
    • Grill
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    2 miles to Skaket Beach, 2 King Beds, 3 ACs & WIFI - This is a classic Cape Cod home in a private location between the Bay and the Atlantic with cooling cross breezes, close proximity to Skaket Beach and Orleans center. This three bedroom, two bath property with a private yard is 2 miles from... View all property information
    Location Information
    Orleans, Cape Cod