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Holiday Rentals 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.
    4 BedroomsSleeps 10Quick View
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    Reviewed 27 August 2015
    Had a wonderful week with our family at this beautiful apartment. It is exactly like the photos! Clean, quiet and relaxing! Would definitely return! The owners live on the...
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    Lovely Summer Rental in East Orleans. Approximently 0.5 miles from Nauset Beach. This apartment will sleep 4. One seperate bedroom with queen bed. Bathroom and shower. Murphy bed available.in sitting area. Comfortable sitting area with Direct TV, WiFi, washer and dryer, microwave among the...
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    Orleans, Cape Cod 02653
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Large wrap around deck provides spectacular views of Cape Cod Bay near Boat Meadow Landing. The Beach IS your front yard! Ideal for children. Relax swimming in the warmer Bay. Two kayaks provided for exploring the Bay and marsh. Take long walks along the water to Rock Harbor. Only a short 5 min....
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    Orleans, Cape Cod 02642
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Terrace
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    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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    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...
    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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    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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    Bright, sunny and updated new home in Nauset Heights with AC! This property is the perfect home base for family and friends to enjoy all that Orleans has to offer. Enjoy a beautiful light-filled living room with views of the ocean, which opens to an updated kitchen and dining room. Beautifully...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Waterfront 4 Bedroom on Crystal Lake in Orleans. This well appointed 4 bedroom has recently been fully updated. It has central AC throughout the home and it is quite spacious! Upper and lower floors all have lake front views. The main level has an eat in kitchen with mini bar with seating for 4....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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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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    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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    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....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Light and bright spacious beach house sitting on the edge of a marsh at the end of a sandy lane-- just 2/10ths of a mile from Skaket Beach! This wonderful spot offers panoramic marsh views with peeks out to the waters of Cape Cod Bay. The recently renovated main floor consists of a lovely kitchen...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cape Cod elegance describes this beautiful, expansive home which sits peacefully at the end of the cul-de-sac adjacent to a cranberry bog. Ideal for the larger gathering with its great room with soaring cathedral ceiling, gorgeous eat-in kitchen, spacious TV loft, screened porch, deck and patio....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Enjoy easy access to a gorgeous private association beach and dock on Pleasant Bay from this well maintained property in the beautiful neighborhood of ''East Egg''. This incredibly spacious home offers lovely water views, central air, large kitchen, and game room with regulation pool table, perfect...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    244 Tonset Road, East Orleans (ID#125800) 2017 Season! Adorable cottage in East Orleans. This home has a screened porch overlooking the private back yard and is located in a nice neighborhood equidistant to Nauset and Skaket Beaches. 3 bedrooms 2 Full Baths, Master Bedroom with private bath....
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    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,...
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    Orleans, Cape Cod
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    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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    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: two new bathrooms, hardwood flooring, water filtration system, Wifi Internet access 55inch TV, DVD . Updated photos to come! Also enjoy relaxing in...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Step back in time in this classic turn of the century cottage with views of Cape Cod Bay. Located on a wonderful property with an expansive yard, a screened-in porch and a path down to the sandy shore of Cape Cod Bay. Additional amenities include: beach chairs, crock pot, room fans, lobster pot,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Reviewed 21 September 2016
    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...
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    *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...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    About this property
    Charming Antique home with 6 bedrooms plus a den providing accommodations for up to 10 guests. Two kitchens, two living rooms, set on a huge lot in the lovely Barley Neck area of East Orleans. All the beds are new, it has been freshly painted and has a great yard. The barn has 2 miniature goats...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 10
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    Nauset Beach!! At this lovely East Orleans vacation rental home you can enjoy the best of Cape Cod. This 4 bedroom, 2 bath home has everything you need for a comfortable stay here in East Orleans. There are A/C units, WIFI internet access,, outdoor grill and plenty of outdoor living space. The...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Reviewed 11 June 2014
    From the moment we drove up the driveway to the time when we finally left, our girls weekend was spectacular! This house that we rented was all we expected and more! Spacious...
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    Classic Cape with bright, modern, free-flowing interior and central air conditioning in a tiny neighborhood on a private road in the woods (but only 2 miles to local stores). Private access to secluded salt-water beach on shallow bay, great for kayaking and beach-combing. Two master suites with...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Spectacular Location! An outstanding waterfront spot offering exceptional privacy. Want to unplug? This simple, rustic cottage (no wifi, no TV) is on a peninsula surrounded by salt water and has views of Mill Pond. Launch your kayak or boat from its shore to access Nauset Inlet and to the beautiful...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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 $60 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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    2013 WATERFRONT HOME! Gorgeous 3-level contemporary home with 180 degree view of a beautiful 28-acre lake and conservation lands. With water views from every room, this dramatic home has 3 exterior decks and a private path to the pond only 75 feet away. Set on a cul-de-sac on a private lane, it is...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    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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    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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    WATERFRONT on Bakers Pond! Take the path from the patio to your private pondfront to enjoy swimming, fishing and kayaking on this lovely freshwater pond. Designed as an airy contemporary cabin on 3 levels-- all with sunset water views-- this home has beautiful pine panelling and hardwood fir floors...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    Orleans, Cape Cod 02653
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Charming remodeled 1930s cottage! This home is located in the desirable and scenic Mill Pond area in Orleans with a well kept yard and wrap-around deck. House is very comfortable with single story living. Three bedrooms (brand new mattresses) and 1 and a half baths are located off the main...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique 3 bedroom home tucked into a wooded path to Nauset Beach. This home offers peeks of the Atlantic from the living room and small viewing deck and distant sounds of the Ocean. Also a second spacious deck for outdoor dining and relaxing, an enclosed outdoor shower, and a portable AC unit in the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Grill
    • Patio
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming modern waterfront cottage-- now with A/C!-- located in the exclusive Mayflower Point section of Orleans where the Namequoit River meets Little Pleasant Bay. The secluded area boasts scenic water views, quiet nights and sounds of birds. The living space has a new whole-house fan, ceiling...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Truly a one-of-a-kind contemporary home on Little Pleasant Bay! Set on over an acre of wooded land, this light and bright beach home has multiple decks, a screened porch and views of the water from nearly every room. Your private beach is just 25 yards away! Sliders in the living room and...
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    Orleans, Cape Cod 02662
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 7
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    6 BedroomsSleeps 14Quick View
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    • Washer
    • Private Garden
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 BedroomsSleeps 6Quick View
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    • Satellite TV
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    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This private gem sits at the end of a sandy lane wrapped in trees and bathed in sunlight. The front deck welcomes you to sit and relax and enjoy the peace and quiet and plan your next days adventure. Located less the 2 miles from Nauset Beach and slightly farther from Cape Cod Bay, this Cape...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Pet friendly
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    Smoking allowed
    About this property
    Freshwater Lakefront! Wonderful, newly renovated cottage set on 1.5 acres on Pilgrim Lake! Bright and open with cathedral ceilings, large fireplace and walls of glass overlooking the lake. This great spot offers much privacy with access to the fresh water out your back door, along with association...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Reviews
    4 BedroomsSleeps 10Quick View
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    • Satellite TV
    • Air Conditioning
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    • Patio
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    • Waterfront
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    About this property
    ** 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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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 BedroomsSleeps 9Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk to the water from this private 4 bedroom, three bath home. Just one house away from a waterview and 200 yards to deeded access to a cove off The River. Nestled within two acres on a gorgeous country dead end road. The sandy beach of Crystal Lake is only .4 mile walk away, Pilgrim Lake less...
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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 BedroomsSleeps 6Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Absolutely charming Cape located in the very desirable Briar Springs area of East Orleans. Situated on a very beautiful and spacious lot, this home is light and bright throughout, offers lovely furnishings and is meticulously kept evoking the feeling of a true vacation get-away. The first floor...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Review
    3 BedroomsSleeps 6Quick View
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    • Ocean Views
    • Satellite TV
    • DVD Player
    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PRICE REDUCTION! The only high season week still open from June 24 to July 1 has just been reduced by 20% to $2,500.00 plus a $100.00 cleaning fee. Thereafter the entire fall season is still open beginning Sept. 2 to Nov. 18 at moderate off-season prices, except 9/9 to 9/16. Yes, we have WiFi and...
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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 BedroomsSleeps 8Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Washer
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Queen bed...
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    Location Information
    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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