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Orleans Vacation Rentals

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    Travelers to Orleans are booking May dates now. Secure your vacation rental today, and have the perfect trip.
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    Cozy studio cottage - within walking distance of the beach and dining!1 / 23
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    NEW LISTING! Tranquil home w/terrace & 2 kayaks-near Nauset Beach & downtown!1 / 24
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream1 / 21
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Rock Harbor Getaway1 / 16
    (3)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed October 10, 2018
    This beautiful home away from home felt cozy and warm from the moment we stepped inside! It was very clean, and decorated with the feel and beauty of the ocean. I especially...
    Reviewed June 9, 2018
    We have stayed here many times and have found the feel of home. The house is perfect for families or just an intimate getaway. Walking distance to the most glorious beach...
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    About this property
    Perfect house for family vacations or weekend getaways! Prime location in the town of Orleans, Cape Cod. Walking distance to town as well as the Harbor. Less than 2 miles to Skaket Beach and 6 miles to Nauset Beach. Full amenities, washer, dryer, dishwasher and an outside Shower! Nicely...
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    True Cape Cod Charm1 / 11
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed August 6, 2017
    Located in Orleans which was in the middle of cape. Good restaurants and shopping. We loved the Christmas Tree Shop. It was easy to drive to other towns North or South. Flew...
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Ocean Views
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    Pet friendly
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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...
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    Orleans, Cape Cod 02643
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    The whole family will find something to love at this riverfront house in Cape Cod, featuring views of the river and plenty of entertainment to satisfy every age in your group. This house boasts a comfortable atmosphere with a cozy wood stove that will make you feel right at home. This house sits...
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    Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Orleans, Cape Cod 02653
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cozy Cottage Overlooking Rock Harbor Creek1 / 16
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Orleans, Cape Cod 02653
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Stunning Carriage House1 / 22
    (1)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Orleans, Cape Cod 02653
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Enjoy the peaceful side of life on the Cape in this stunning home, close to Nauset Beach! With a private hot tub, spacious master bedroom on the top floor with a jet tub, and two gas fireplaces to relax in front of after a long day of exploring, this home has the room and amenities for the whole...
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    Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 8
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    Panoramic Views of the Atlantic1 / 26
    (6)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Reviewed November 9, 2016
    The house is designed perfectly for a couple of families who want to rent a beach house for a week or two. It is not only well-designed and practical, but is also spotless and...
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    Escape the hustle and bustle of the city when you stay at this charming Orleans studio! Perfect for a couple, a small family, or a few close friends, this vacation rental offers easy access to Nauset Beach and features modern home conveniences including cable and free WiFi. SeaWind Guest Studio...
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    Orleans, Cape Cod 02653
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This 2 bedroom condo is equipped with kayaks and canoes right on the association dock. (First come first use with a few other condo units.) Renovations include air conditioning, new hardwood floors, new windows, outside shower, and additional half bath. The main level offers a fully stocked kitchen...
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    Orleans, Cape Cod 02653
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    On the Waterfront of Nauset Heights1 / 43
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Yard
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    Smoking allowed
    About this property
    Our charming home is well appointed with all you need to have a great vacation. Air conditioned, fully furnished kitchen to make your meals, barbecue grill in the backyard. The deck is surrounded by mature trees and plants adding a beautiful setting for a relaxing vacation. A fabulous outdoor...
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
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    • Housekeeping Included
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location! This charming two bedroom beach cottage, which was fully renovated in 2018, is ideal for your Cape vacation. Nestled on a private road, this little piece of heaven is conveniently located to literally everything the Cape has to offer: Robert’s Cove (a 2-minute walk...
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    Orleans, Cape Cod 02653
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    On the Banks of Rock Harbor Creek1 / 36
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Private, beautiful family home located on a child-safe street in East Orleans. Three levels of living for a maximum of 10 people. Plenty of room for all. The deck with dining table overlooking private back yard is located off the kitchen. Outside shower and spacious back yard. Garage is where...
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    East Orleans, Orleans 02653
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    • Ocean Views
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Walk to Nauset Beach and National Seashore from this charming home!1 / 27
    (1)Terrible
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Balcony
    • Grill
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    • Patio
    • Terrace
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    • Central Heating
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    Pet friendly
    Kid friendly
    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    #515:  Brand New Renovation - private beach just 10-feet from Crystal Lake1 / 31
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed October 24, 2018
    This was a wonderful rental. Very clean and well maintained and equipped. I highly recommend this place. The dock was an added pleasure!
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Located just 2 miles from Nauset Beach, this property has it all: plenty of land to roam, picturesque grounds, proximity to the ocean and four goats to keep you company. Welcome to Barley Neck Farm. This 19th century farmhouse has been recently renovated with the outmost care. Original details...
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    Orleans, Cape Cod 02653
    Rental Home - 7 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Sauna
    • Private Outdoor Pool (Unheated)
    • Hot Tub
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    About this property
    Luxurious Orleans Home with Private Salt Pool, Sleeps 10, Linens included Peak Summer Weekly Rate: $9,500 Rents Saturday to Saturday during peak season PLEASE NOTE: The new Massachusetts state and local taxes apply to stays starting July 1 or later. Book in June and save! Located on a large...
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    Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Executive Waterfront Luxury Home. A/C; Heated Pool & Elevator1 / 29
    (1)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Washer
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 22, 2018
    We just had a glorious week enjoying the incredible views, the majestic house and pool, and of course the natural beauty of the Cape. We have rented our fair share of properties...
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    About this property
    This 6000 sq-ft luxury Estate is a gracious oasis of tranquility with mesmerizing views suitable for family vacations & executive corporate retreats. This luxurious estate features four large Master Bedroom Suites, Elevator, A dinning room that seats 16, Large Living Room, Great Room, Game/Media...
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    East Orleans, Orleans 02653
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 16
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    26 Tides End Lane, East Orleans MA (ID# 52984) 2019 Season! Waterfront home with private dock on Meetinghouse Pond and access to Pleasant Bay. Casual living with water views from almost every room. Picturesque grounds and a nice sunny porch is just about everything you need to enjoy your Cape Cod...
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    East Orleans, Orleans 02653
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    A Private Sunny Gem1 / 14
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    10 Captain Curtis Way 184361 / 17
    (2)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    10 Captain Curtis Way, Orleans (ID#18436) 2019 Season! Cute as a button with Seaside touches and well equipped for your Cape Cod Vacation! Located on a lovely, quiet street with easy access to Nauset Beach and the Village of East Orleans. Living/Dining/Kitchen Area is centrally located with 2...
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    East Orleans, Orleans 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Located right on the shore of beautiful Town Cove in Orleans. This family home has 4 bedrooms 2 baths and a view of the water which is special. This classic Cape Cod home is one floor living with all 4 bedrooms on the main floor. The master has a King with private bath with a walk-in shower, BR2...
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    6 Cedar Land Road, East Orleans (ID#18315) 2019 Season! Adorable home in East Orleans 6/10 mile to Nauset Beach with central air conditioning. This 2 bedroom/1 bath home features an open kitchen/living room and den/TV room leading to the deck and back yard. The bedrooms are furnished with 2 twins...
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    East Orleans, Orleans 02653
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Unit 11 372461 / 9
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    170 Beach Rd Unit #11 (ID# 37246)~Oceanside one bedrom Cottontail Cottage~A/C Nauset Beach Area 2019 Season! This adorable one bedroom cottage is located less than 1/2 mile from beautiful Nauset Beach on the Atlantic Ocean! After a day of fun in the sun, gather in the outdoor eating area and enjoy...
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    East Orleans, Orleans 02653
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Walk to Meetinghouse Pond, 3 season porch, pet friendly This beautiful Cape Cod home sits on Barley Neck, a small peninsula just a few minutes drive to Nauset Beach. Surrounded by Meeting House Pond and Little Pleasant Bay, this area is harbored from the Atlantic Ocean by Pochet Island. From this...
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Prestigious location within Quanset Harbor Club Association. Built on 1.3 acres and only 3 houses away from the community’s private beach on beautiful Pleasant Bay. This is the perfect property to enjoy all that Cape Cod has to offer. Home is newly furnished with a new gourmet kitchen with high end...
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    Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    6 Bayberry Way 185911 / 20
    (2)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    6 Bayberry Way, East Orleans MA (ID# 18591) Waterfront and Waterview on Meetinghouse Pond 2019 Season! Kayak or Canoe- this is the perfect location! Water front on Meetinghouse Pond with access to The River and to Pleasant Bay and less than 2 miles to Nauset Beach. This home offers Air Conditioning...
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    East Orleans, Orleans 02653
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Great location. Short walk down Beach Road to Nauset Beach, which many call the best Cape Cod beach. Spacious master bedroom on top floor. Beautiful view toward Nauset Beach from upper deck. Contemporary style. Beautiful lawn and plantings. East Orleans is part of the Quiet East Side of the...
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    East Orleans, Orleans 02653
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    238 Tonset Road, East Orleans (ID# 113528) 2019 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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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 living...
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    244 Tonset Road, East Orleans (ID#125800) 2019 Season! New kitchen as of October 2018! Adorable vacation rental located in East Orleans. This property has a screened porch overlooking the private back yard (with patio and fire pit) located in a nice neighborhood equidistant to Nauset Beach on the...
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Pleasant Bay Retreat1 / 19
    (4)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Quiet Home in East Orleans1 / 18
    (1)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Orleans, Cape Cod 02653
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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