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Orleans Vacation Rentals

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    Travellers to Orleans are booking August dates now. Secure your vacation rental today, and have the perfect trip.
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Located beside Cedar Pond which is great for fishing, this home offers all of the privacy and convenience you could ask for while enjoying your Cape Cod vacation. Walk to Main Street and the Bike Trail in less than a half mile or bike to beautiful Skaket Beach - just a mile away! This home has a...
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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 6 Quick View
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    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...
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    Orleans, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    27 Pond Road, Orleans (ID# 22347) 2017 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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    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Porch
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    Absolutely wonderful young 4 bedroom, 3 full bath cape house with open floor plan on private and quiet cul de sac street off Beach Road. This year just got totally renovated kitchen and bath with modern amenities. Only 0.8 mile from the magnificent Nauset Beach!- One of the best beaches in Cape...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Recently renovated, spacious two-bedroom home with CENTRAL AIR-CONDITIONING sleeping six tucked up on a wooded knoll at Bakers Pond. This spot offers much privacy and is less than .1 mile to beautiful freshwater swimming and kayaking on the pond. This location feels removed from it all, yet is only...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Great privacy in East Orleans! Enjoy this lovely 3-bedroom, 2-bath contemporary saltbox offering a bright and open floor plan and updated furnishings. Front-to-back living room with fireplace and a great screened porch open onto a spacious wraparound deck. This great vacation spot is gracefully...
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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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    Newly renovated ranch located on a cul-de-sac in the desirable Brick Hill area of East Orleans. Fresh, bright and open with Central Air Conditioning! Enjoy the newer furnishings throughout and all amenities. A great spot convenient to the sandy shore of Nauset Beach and The East Orleans Village....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charming period home located only 2/10ths of a mile from gorgeous Nauset Beach on The Atlantic. Enjoy the sunny deck, comfortable furnishings, wonderful country kitchen and spacious backyard. Attached apartment also available for rent. Additional amenities include: room fans, lobster pot, cd,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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, 2 Bathrooms, Sleeps 8 Quick View
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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,...
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    Orleans, Cape Cod 02643
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    Just 0.3 miles to Private Pleasant Bay Beach!! This 4 bedroom / 2 bath home features nice furnishings and amenities with access to a deeded path to a private beach on Pleasant Bay. It is about 3/10ths of a mile to the beach. The path is up a slight hill and wooded. The first floor features a...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Enjoy a serene setting with amazing views from this 3 bedroom Orleans home. Bring your kayaks & canoes to take full advantage of the lake front location. A private boat dock makes accessing the lake for swimming or boating easy. This home offers a nice open layout with views from almost every room...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Secluded Cape Cottage, 3-5 Minute Walk to Beach $2,100 PRIME SUMMER WEEKLY RATE (Rents Saturday - Saturday during peak season) 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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    This recently remodeled 3 bedroom just 1.5 miles or a 5 minute drive 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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Min walk Nauset Beach, Ocean View1 / 26
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    ** Please note: $500 Minimum for off-season stays!** 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!...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    NEW LISTING! Charming 2-bedroom cottage in East Orleans, on a private lane off Tonset Road. The bedrooms have a queen, and 2 twins; full bath features a heat lamp. Eat-in kitchen open to living room with ductless A/C unit to cool the cottage. Only a half-mile to Tonset Harbor beach for swimming and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    #503 - the Ocean Loft: This beautiful fully-renovated barn loft is a perfect place to spend time relaxing and soaking up the summer sun poolside. Brand new wood floors, multiple skylights and exposed beams makes this bright and airy loft an ideal place to spend time recharging from a long day at...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    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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    10 Shorewood Drive 184021 / 16
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    10 Shorewood Drive, Orleans MA (ID# 18402) ~ Near Bakers Pond 2017 Season! Bright and airy home in quiet neighborhood with easy access to Bakers Pond (26 acre kettle pond stocked with trout) or Nickerson State Park a block away where you can enjoy fresh water activities and hiking. Comfortable...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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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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    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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    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Very spacious and nicely appointed home with two living rooms perfect for the larger get-together. Located on a wooded lot close to Little Pleasant Bay and the Paw Wah Pond boat ramp. Enjoy the nice deck and all amenities, including a refurbished kitchen and new flat-screen TV-- plus CENTRAL A/C!...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Charming Cape, just off historic Town Cove. With two bedrooms down, one up, plus a child's nook, this comfortable home can accommodate 7 guests. Features bathrooms up and down; a sunny family room/dining area; fully-equipped kitchen; and a cozy living room with fireplace. Only a short walk to Asa's...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Bright, open and very spacious Cape centrally located on a cul-de-sac not far from Skaket Beach, Rock Harbor, The Cape Cod Rail Trail and Orleans Center. A wonderful, very well maintained home-- with a large deck ideal for eating summer meals or reading a book. Now with A/C units in the living...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    NEW LISTING! Charm oozes throughout this adorable duplex condo with 180 degree water views of Town Cove. This lovely spot is in a quiet in-town location within walking distance of shops, restaurants, live theatre and baseball games! Two bedrooms, one with a queen and slider to deck; the other has a...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This charming Cape sits on a large lot on a quiet street in Orleans. This is a great location with easy access to Skaket Beach, the Rail Trail for biking and also easy access to shops and restaurants. The deck overlooking a large yard is a great place to relax and unwind at the end of a busy day at...
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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 10 Quick View
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    Retreat to this cozy Cape Cod home less than a mile from two amazing beaches, complete with two inviting living spaces and a nice deck with a gas grill. This home is located in Orleans, MA, about a mile from Nauset Beach and Skaket Beach - two top destinations on Cape Cod during the summer months....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    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 beaches, or, if you prefer,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    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: $4,600 - $4,900 Expansive Waterfront Home on Crystal Lake in the heart of Orleans. Crystal Lake is a pristine fresh water lake located close...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Bright, Pet-friendly, beach cottage just 0.2 miles to Skaket beach!1 / 20
    (1)Average
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Price Range $1875-$2375* *without pet $100 less Rates include all charges; no hidden fees! Now pet-friendly! This bright single level beach cottage just 0.2 miles to Skaket beach features a beautifully landscaped yard and a large deck. It is a great Cape Cod getaway. Enter into the living room and...
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    Orleans, Cape Cod 2653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    This immaculate home is located in a quiet neighborhood with just a .2 mile walk down a sandy path to Skaket Beach. It is also close to the bike trail and nearby shopping and restaurants. The home features an open floor plan with skylites, a spacious screened porch with seating, and a large back...
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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    5 Blueberry Island Road, Orleans, MA (ID# 18404) 2017 Season! Bright and spacious home just a short distance to Cape Cod Bay and Skaket Beach! This wonderful home provides all amenities and has cathedral ceilings in the living, dining and kitchen areas. 3 Bedrooms (2 Queens, 2 Twins) and 2 Baths....
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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
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    4 Seaview Rd East Orleans (ID #130778) ~ Oceanside Two Bedroom cottage ~ Mill Pond Area 2017 Season! Darling little Cape cottage. Enjoy simple summer living in this peaceful setting of cottages near Mill Pond. This property offers wireless internet, two comfortable bedrooms with A/C units, bright...
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    Location Information
    Orleans, Cape Cod 02653
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    ASP-9991 / 16
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Renovated ranch with semi-finished lower level walkout tucked up on a hill in the lovely Brick Hill area of East Orleans. This nice vacation home is fresh and bright offering newer furnishings and convenience to the East Orleans Village and Nauset Beach. Three bedrooms accommodate 6 guests, with...
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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    12 Heritage Dr. 1188991 / 24
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    12 Heritage Drive, Orleans MA (ID#118899) 2017 Season ! Lovely, spacious updated colonial home near Pah Wah Pond and equidistant to Nauset Beach or Skaket Beach and centrally located to Pleasant Bay, Chatham and National Seashore Beaches. A gorgeous kitchen with stainless appliances and granite...
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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    2 bedroom 1 bath apartment with separate private entrance, driveway and deck. Living room, kitchen, and laundry. Queen bed in one room and a double bed in the other room. Optional air mattress can be set up in living room to sleep 2 more if needed. Window AC units in bedrooms. Ceiling fans in...
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    Location Information
    Orleans, Cape Cod 02653
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
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    • Terrace
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    • Balcony
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    This immaculate, well appointed Cape enjoys access to all of the amenities of Orleans. Its close proximity to Skaket Beach, Rock Harbor, Orleans Center and the Bike Trail make it an ideal vacation property for the active family. With three bedrooms, 2 baths and an extra sleeping area with a daybed,...
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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Priscilla Landing1 / 26
    (6)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lovely 3 bedroom, 1.5 bath East Orleans Cottage located in a quiet and private area of East Orleans convenient to great waters for kayaking, paddle boarding, walking along the water edge and Nauset Beach. This cute cottage has WIFI, flat screen TV, nice deck and yard, outdoor shower, A/C, cooking /...
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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    A VERY SPECIAL HOME FOR 6 VERY SPECIAL GUESTS IN NAUSET HEIGHTS!1 / 24
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Price $1875-$2275 Rate includes all charges; no hidden fees! Recently purchased by new owners, this beach cottage has undergone a face lift to maximize the exterior and interior space and to completely redefine the meaning of rustic from its 20th century images of musty rugs and knotty pine. The...
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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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