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Orleans Holiday Rentals

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    Travellers to Orleans are booking September dates now. Secure your holiday rental today, and have the perfect trip.
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    FABULOUS SUNSETS & BAY VIEWS ON WATERFRONT PROPERTY1 / 16
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Walk to Nauset Beach and National Seashore from this charming home!1 / 26
    (1)Terrible
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    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, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Price Range $1595-$2195* *without pet $100 less Rates include all charges; no hidden fees! This delightfully redone 2.5 bedroom/1.5 bath home located in a sought-after East Orleans location is bright and open with an unbeatable location! The front door leads directly into a large living room cooled...
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    Orleans, Cape Cod 2653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This recently renovated 2 bedroom,1 bath cottage is nicely appointed in a prime East Orleans location, convenient to beaches and shopping. It is situated across the street from Town Cove and Asa's Landing and offers views of the water. The cottage has lovely grounds and gardens to enjoy, as well as...
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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 6 Quick View
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    Price Range $1895-$2245 Rates include all charges; no hidden fees! Situated between Skaket Beach on the bay and Nauset Beach on the ocean, this beautifully renovated home is tucked in a quiet neighborhood. It is a short walk to playgrounds, public tennis courts, the town of Orleans for great...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Price Range $2415-$3915* *$100 less without pet Rates include all charges; no hidden fees! NEW LISTING! PROPERTY UNDERGOING COSMETIC UPGRADES! NEW PICTURES COMING SOON! The moment you arrive at this 3 bedroom, 3 bath classic cape with central a/c, you will immediately downshift into vacation gear....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    • Balcony
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    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 Bedroom by Nauset Beach1 / 18
    (4)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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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    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 10 Quick View
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    • Internet Access
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    Pet friendly
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    About this property
    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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    This light & bright newly listed home is situated on a quiet, dirt road and offers an easy 4/10th of a mile walk to Skaket Beach. It has 2 bedrooms on the first level, one with a queen sized bed and the second with 2 twins. There is also a cozy, open layout with a living area and updated, eat-in...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sweeping Bay Views, Privacy, Two Full Kitchens (Pets Considered) Peak Summer Weekly Rates: $4,300 - $4,500 (Rents Saturday - Saturday during peak season) 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...
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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 8 Quick View
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    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...
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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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    Price $3195 Rates include all charges; no hidden fees! SKAKET BEACH is just 3/10th's of a mile away via path at Willie Atwood Rd and Cape Cod Rail Bike trail access is very close to this splendid Orleans home! This 4 bedroom home with Central A/C is set on almost an acre of land down a sand lane,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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...
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    Orleans, Cape Cod
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Luxury 6 BR Home W/ 60 Foot Private Pool1 / 23
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
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    • Sauna
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    • Private Outdoor Pool (Unheated)
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    About this property
    This warm and inviting 6 bedroom, 4 bath home sprawls over 4 stories of comfortable rooms with spacious, open living areas and a private, fully fenced back yard. Perfectly located in South Orleans, the house is just minutes from the Lower Cape villages of Chatham, Brewster and Orleans. A beautiful...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Price Range $1875-$2475* *without pet $100 less Rates include all charges; no hidden fees! New Bedroom suite, recently expanded living room, Flat screen TV's and 2nd bath! This quaint 3 bedroom, 2 full bathroom Cape Cod Vacation Cottage is located on a spacious corner lot located just 3/10 of a...
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    Orleans, Cape Cod 2653
    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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    Price Range $1745 Rates include all charges; no hidden fees! This idyllic 3 bedroom/1 bath home sits at the end of a quiet cul-de-sac. A down to the studs renovation was designed to maximize space and sunlight. Its cheerful interior combines whimsy and practicality in every room. You walk through...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Satellite TV
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    • Private Outdoor Pool (Unheated)
    • Hot Tub
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    Pet friendly
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    About this property
    Private Orleans resort with water views, heated pool & spa; sleeps 14 (linens included) NEW Listing for 2017! Peak Summer Weekly Rates: $15,900- $16,900 (Rents Sunday to Sunday during peak season) Your multi-generational or multi-family summer vacation has found its home. Enjoy panoramic views of...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 15
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This cute 2 bedroom, 2 bath waterfront condo sits on beautiful Skaket Beach in Orleans. It is a second floor, end unit with unobstructed views of Cape Cod Bay. The property features two bedrooms, one with a queen sized bed and one with two twin sized beds, as well as a double pull out sleeper sofa...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This is a unique ranch in beautiful East Orleans. It has a private small dock in Meetinghouse Pond, a saltwater estuary of Little Pleasant Bay. Fully renovated in winter of 2016 this property sits on an oversized private lot and the owner is a high end landscaper who will finish exterior hardscape,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    About this property
    Nice 2 bedroom, 1.5 bath home so close you can WALK to your own private association beach on PLEASANT BAY. When you walk in the front door you go up a few stairs to get to the main level. The first level has a nice living room/dining room, a galley kitchen, and a relaxing 3 SEASON ROOM where you...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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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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    ORLEANS 3 BEDROOM 2 BATH VERY CLOSE TO NAUSET BEACH!1 / 22
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 31 May 2017
    My husband and I rented this wonderful, warm and inviting contemporary home for a week and didn't want to leave. It is conveniently located in East Orleans where you'll find...
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    Price Range $1795-$2595 Rates include all charges; no hidden fees! This beautifully decorated three bedroom, two bathroom East Orleans home with bright, open contemporary style and is located just a mile to Nauset Beach! Upon entry to this home you will find soaring ceilings with wood beams,...
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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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    About this property
    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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    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 (Rents Saturday - Saturday during peak season) 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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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...
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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 8 Quick View
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    About this property
    A very unique haven situated on what was a private family compound with private beach on Cape Cod Bay. The beach is less than 700 feet away via a beautiful sandy path which passes a cranberry bog along the way. The rambling, airy & bright 3000 sq. ft. home has been renovated over the past several...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Price Range $1245-$1670 Rates include all charges; no hidden fees! Enjoy this Lakefront condo on Crystal Lake and near the heart of Orleans close to dining and shopping and more! A quick ride to Nauset Beach which is 3 miles from this home. This condo home has everything to offer including kayaks,...
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    Orleans, Cape Cod 2653
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Very convenient to everything Orleans has to offer, this well appointed home is just a short drive to Nauset Beach or town. This 4 bedroom, 2 bath home sleeps 8 comfortably, making it ideal for extended families. The property offers a nicely landscaped yard, deck, and patio as well as a gas grill...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    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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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Beautiful historic home, private mini estate. Heated Pool, Central AC, Sleeps 13, Linens & Towels Included, Pets considered! Peak Summer Weekly Rates: $7,500 - $9,500 (Rents Saturday - Saturday during peak season) The interior of this beautiful 1920 Orleans home was fully remodeled and redecorated...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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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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    Spacious Orleans Home on Crystal Lake Includes Linens and Beach with Kayaks, Canoe & SUP Boards! Peak Summer Weekly Rates: $5,400 (Rents Saturday - Saturday during peak season) This expansive waterfront home is located on Crystal Lake in the heart of Orleans. Kayaks, a canoe and stand-up paddle...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Smoking allowed
    About this property
    Escape to Cape Cod and enjoy being just a few blocks from the beach at this adorable three-bedroom duplex for six. Located in the small town of Orleans, you'll have lots of room plus a great outdoor space at this home, complete with a nice patio, grill, and outdoor shower. This home is located in...
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    Orleans, Cape Cod 02643
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Price Range $1695-$1995 Rate includes all charges; no hidden fees! This very special 4 bedroom, 3 bath vacation rental features handsome wood floors and central air-conditioning. Located on a wooded lot, you can paddle board, kayak, or boat in adjacent Areys Pond, swim in nearby Crystal Lake, body...
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    Orleans, Cape Cod 2653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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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 Cod...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Grill
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    • Hot Tub
    • Sauna
    • Private Outdoor Pool (Unheated)
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    Smoking allowed
    About this property
    Private Orleans resort-style compound with heated pool & spa, fire pit and cabana (linens included) NEW Listing for 2017! Peak Summer Weekly Rates: $12,500 - $14,000 Last minute deal! Week of Aug 13th reduced 15% to $11,200/week (Rents from Sunday to Sunday during peak weeks) Please click on the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Brand new renovation! Light and bright expansive ranch that has been beautifully and thoughtfully upgraded throughout. This architech-designed 'green' home is pristine and feels brand new! A few of its many highlights are its wonderful great room offering additional living space, inviting deck...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    About this property
    Enjoy the comfort of this conveniently located and well-appointed newer home. Nauset Beach (oceanside) with full amenities (restrooms, outdoor showers, Liam's for seafood, burgers, ice cream and more) is just a short drive (3.5 mi) from the house. Skaket Beach on the Cape Cod Bay with its long...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Spacious Bay Side Orleans Waterfront Home Next to Skaket Beach PEAK SUMMER WEEKLY RATE: 8,500 (linens included) Please click on the "Virtual Tour" to see a 3D tour of the home Situated between Skaket Beach and Rock Harbor, this magnificent home leaves nothing to be desired. Commanding views and...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    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,...
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    Orleans, Cape Cod 02643
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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