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Orleans Holiday Rentals

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    Travellers to Orleans are booking May dates now. Secure your holiday rental today, and have the perfect trip.
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    Cape Cod ~Cozy  Relaxing Vacation Apt.1 / 6
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Bright & Charming Cottage: on the way to Nauset Beach, Walk to Sundae School!1 / 21
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    This 3 bedroom, 1 bath Orleans home is within walking distance of picturesque Rock Harbor and Cape Cod Bay. The first bedroom features a king sized bed, the second a double sized bed and the third has one twin sized bed. The spacious living room also offers a pull out sleeper sofa for extra...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    61 Captain Linnell Road, Orleans, MA (ID# 100002) Near Skaket Beach 2017 Season! Spacious, beautifully updated, dog friendly home near Skaket Beach on Cape Cod Bay. Large granite and stainless kitchen opens to dining area, living area and office. Sliders to deck, brick patio, back yard and fire...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    #501 Viking Cottage: New renovation, sunny secluded home with view & access to saltwater. Enjoy the pleasures of a waterfront property -- Wake up to views of a peaceful Pleasant Bay inlet from this sun-filled, modern 3-bedroom cottage in the woods. Launch your kayak or canoe to explore beautiful...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    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 Cod...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Enjoy this gorgeous custom 3 bedroom, 2 bath East Orleans vacation rental that is located just 1/10th of a mile from some of Cape Cod s best inner water ways off of Pleasant Bay and minutes from Nauset Beach & East Orleans Village. This rental home has been tastefully designed with high-end...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Walk to Nauset Beach and National Seashore from this charming home!1 / 26
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Enjoy dining al fresco on the patio with a gorgeous ocean view at this cozy Cape Cod home. Grab one of the two beach chairs and head to Nauset beach, just a few blocks away - you'll be relaxing in no time! Additional area beaches are nearby and you're also not far from the fishing mecca of Mill...
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    Orleans, Cape Cod 02643
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    This lovely 3 bedroom, 2 bath East Orleans vacation rental is located 1.9 miles to Nauset Beach in East Orleans and just 3/10ths of a mile to Nauset Farms Market, Sundae School Ice Cream and Zia s Pizzeria. At this private and quiet location you can enjoy the beautiful outdoor living area and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    #502 The Lobstah Pot: East Orleans at its finest. This quaint and FULLY RENOVATED cottage is a short walk to preservation land and a salt water bay worthy of kayaking. Bring your bikes for a fast 10-minute ride to Nauset Beach or your kayaks for unending exploration in Town Cove, Mill Pond and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Hot Tub
    • Waterfront
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    Renovated Gem on Town Cove in Orleans with hot tub, walk to town Peak Summer Weeks: $4,400 - $5,400 Please note:  This property rents Sunday to Sunday in summer for full-week or multiple week terms only, but is available during the shoulder-season for 3-night minimum. This Orleans home is located...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Delightful ranch located in the Nauset Heights area of East Orleans, just .2 miles away from Nauset Beach! The house is bright and cheerful with a nautical theme and features a deck offering peeks of the Atlantic Ocean. With four bedrooms and 2 baths, it sleeps 8 comfortably. The first floor...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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...
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    Orleans, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    7 Mallard Drive, Orleans MA( ID# 49614) Close to Skaket Beach 2017 Season! Wonderful home near Skaket Beach, A/C, private yard, quiet neighborhood! Just under 1 mile to Skaket Beach from this beautiful 3 bedroom, 3 bath home on the bayside of Orleans! Spacious home with all of the desired...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    20 Hayward Lane, East Orleans (ID# 108991) Close to Nauset Beach MeetingHouse Pond, Pleasant Bay and Village of East Orleans 2017 Season! Enjoy this lovely, large, sun-filled home in charming East Orleans on a spacious, 1.5 acre private property with saltwater views of Frostfish Cove (leading to...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
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    For the ultimate Cape Cod retreat, stay at this charming shingle-style cottage in Orleans. You'll have stunning views of the water just out your back door, a cozy interior with a fireplace, and plenty of outdoor space on the deck and sunroom - complete with a gas grill. Located in the ocean town of...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Balcony
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    • Terrace
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    Pet friendly
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    Smoking allowed
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    When it's time for your next vacation, make this prime lakefront Orleans home yours, and enjoy beautiful views in a secluded, tranquil setting with close proximity to town. You'll have access to private and public docks and two kayaks. Ideal for large families, couples, or groups, this home offers...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    244 Tonset Road, East Orleans (ID#125800) 2018 Season! Adorable vacation rental located in East Orleans. This property has a screened porch overlooking the private back yard located in a nice neighborhood equidistant to Nauset Beach on the Atlantic Ocean and Skaket Beach watch the sun set over...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Nauset Heights! Absolutely lovely, newly built guest house located just under a half mile from the sandy shore of Nauset Beach on The Atlantic. Designed with the cozy character of a barn with the finer amenities of today. Beautifully detailed throughout with authentic wide pine floors, sliding barn...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Skaket Beach at just 2/10ths of a mile, gorgeous marsh views and has been completely renovated & newly furnished in 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 bedrooms , 1 full...
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    Orleans, Cape Cod 02753
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    238 Tonset Road, East Orleans (ID# 113528) 2018 Season! Charming home near Town Cove and Asa s Landing. This beautifully decorated, pristine 3 bedroom home also has an adorable 1 bedroom cottage right next door. Perfect for the group that needs a little privacy or extra room. Equipped with...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    17 Center Place 183741 / 10
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    17 Center Place, Orleans MA (ID# 18374) Close to town, waterfront to pond 2017 Season! Charming waterfront cottage on scenic Boland Pond. A good location, only a short distance to the center of Orleans, not far from the bike trails and to Skaket and Nauset Beaches! 2 Bedrooms, 1 Bath. Sleeps a...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    26 Winslow Drive, Orleans (ID# 18543) ~ South Orleans 2017 season ! Located in South Orleans and close to Chatham for shopping and dining! This home is less than ½ mile to the beaches on Pleasant Bay and overlooks scenic Uncle Seth’s Pond. This contemporary home with an abundance of glass offers...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This Orleans property features stunning views of Robert's Cove from almost every room in the house. This custom built home has a casual floor plan that takes advantage of the serene waterfront setting, as well as comfortable furniture for relaxing. Enjoy the pathway around Robert's Cove or bring...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This custom designed home was renovated just a couple years ago and is newly furnished and tastefully decorated. It has all the comforts and conveniences of home: bedroom A/C units on each floor; GenAir cook top with grill and griddle; double oven; gas & charcoal grills; 4 TVs, including new 36”...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Waterfront on Nauset Harbor! Classic Cape located on an incredible property overlooking the water and beyond. Enjoy the lovely living area with fieldstone fireplace, relaxing on the spacious deck or taking the path to the shore's edge. Current updates include new carpeting throughout house,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    22 Uncle Vicks Way 184011 / 14
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    22 Uncle Vicks Way, , MA (ID# 18401) 2017 Season! Cape Cod Summer Vacation. A charming Cape ranch located close to town and the East Orleans Village. This home offers a lovely private setting, nice country furnishings and a lower level family room. Ideal vacation home with 3 bedrooms and 2...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2 miles to Skaket Beach, 2 King Beds, 3 ACs & WIFI 'Ready to Rent for the 2018 Season' 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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Salt waterfront home located in the Ocean Harbor Association in East Orleans. This newly-furnished home is set on over an acre of beautiful multi-level grounds with frontage and views of Little Cove. Enjoy kayaking right from your backyard, access to the association tennis courts or deepwater...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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 $75 reservation fee and a refundable security deposit. - Additional amenities include: coffee maker,...
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    Orleans, Cape Cod
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
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    • Private Garden
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    Come to your very own private resort on Cape Cod. Located directly on Nauset Harbor on the Eastham\Orleans town line, The Jeremiah House is the place to be for your quintessential Cape Cod getaway. This luxury home is the perfect convergence of classic old Cape Cod architecture and charm with...
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    Orleans, Cape Cod 02642
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Just a short distance to the center of Orleans, this well kept Saltbox style house is convenient to everything. It is only .3 miles to the bike path and 1.6 miles to Skaket Beach. The large grassy yard is private and spacious. The cute back deck comes equipped with an electric grill and outdoor...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Charming ranch on a quiet lane offering a idyllic setting right on Henson's Cove. There are many ways to enjoy the outdoors at this wonderful location. Bring your kayak or canoe to paddle Pleasant Bay, enjoy beautiful fresh water swimming at nearby Crystal Lake, walk the conservation land of Kents...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    25 B Doane Road, East Orleans (ID# 106441) Nauset Heights 2017 Season! Adorable 2 bedroom cottage in Nauset Heights. Peeks of Mill Pond and around the corner from the landing. Cute, clean and charming 2 bedroom, 1 bath cottage with central air conditioning, part of the Pilgrim Lane cottages....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    About this property
    Spacious 4 Acre private waterfront estate located in the prestigious and secluded Snow Point Association with private steps down to the water. Snow Point is a small peninsula of land in Orleans bordered by Rachel Cove, Town Cove and Woods Cove. You'll experience 180-degree views of the water from...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    JUST LISTED! Waterfront on Skaket Beach! TWO-bedroom ground level condo in 4-unit waterfront building. Enjoy the sandy shore of Cape Cod Bay right outside your door. There are 2 twins in one bedroom, bunkbeds (twins) in the other and a twin daybed tucked in the corner of the living room. This...
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    Orleans, Cape Cod 02653
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    20 Deerwood Lane, East Orleans, MA (ID# 120896) 2017 Season! Wonderful Home in East Orleans with central A/C. Walk to restaurants or Sundae School after a relaxing day at Nauset Beach. This dog friendly (with homeowner approval) home features lots of room with 4 bedrooms, hardwood floors...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedroom by Nauset Beach1 / 18
    (4)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2017
    We couldn't be more pleased with our stay at this cottage. Tucked away in the beautiful Nauset Heights area it was the ideal vacation spot. We had kid-friendly walks to inlet...
    Reviewed 8 September 2016
    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...
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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....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    27 Pond Road, Orleans (ID# 22347) 2018 Season! Nestled on a private 1.5-acre wooded lot, this charming and newly constructed home combine’s comfort with gracious living! The large kitchen features high-end appliances, marble counters, breakfast booth with bay windows and opens to the dining area...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    Adorable cottage located in a beautiful, quiet area about 3/10ths of a mile from Nauset Harbor. The cozy living/dining/kitchen area features a brand new kitchen, queen sofa bed and A/C unit. The bedroom has a king bed (easily converted into 2 twins) and an A/C unit. A separate laundry area has a...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
    • Hot Tub
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    About this property
    Private Orleans resort with water views, heated pool & spa; sleeps 15 (linens included) Peak Summer Weekly Rates: $15,900- $17,800 Rents Sunday to Sunday during peak season Please click on the 'Virtual Tour' to see a 3D tour of the home Your multi-generational or multi-family summer vacation has...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 15
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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. All bedrooms have window A/C units. We are on a quiet wooded lane, just one mile from...
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    Orleans, Cape Cod
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Smoking allowed
    About this property
    Comfortable 4 bedroom home located on a quiet dead end road just a short distance from Rock Harbor and the Cape Cod Rail Trail. For the 2017 season: both bathrooms updated, hardwood flooring, water filtration system, Wifi Internet access 55inch TV, DVD . Central Air! Also enjoy relaxing in the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Smoking allowed
    About this property
    This classic 4-bedroom, 2-bath Orleans, MA vacation rental is set so close to treasured Nauset Beach you can hear the waves from home. Relax, unwind, and enjoy Cape Cod with the people you love! A large and beautifully furnished home with a fireplace in the main living area, charming areas for...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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