Latest Vacation Rentals in Orleans MA (374)

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3 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

Light and bright East Orleans cape 1.8 miles to Nauset Beach! Beautifully decorated in a Cape Cod beach theme this home is also convenient to Orleans Main Street shops and restaurants. Main level...

Created Dec 4, 2022

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3 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

Family and pet friendly property centrally located not far from the Cape Cod Baseball League field and the home of the Orleans Firebirds.This one level traditional Cape style home offers a fully...

Created Dec 4, 2022

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2 Br Private Vacation Home Vacation Rental In East Orleans, Massachusetts

Ocean view and just a 10 minute walk to Nauset Beach and the Atlantic Ocean, The Friendship House offers home away from home comfort for a small family or a couple. A large bright fully-equipped...

Created Dec 4, 2022

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5 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

Charming antique style home with large country kitchen, living room, card/game or use room as back up eating room, master bedroom, master bath and laundry on first floor. On second floor- three...

Created Dec 4, 2022

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4 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

Orleans CoveOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'An exceptional stay awaits at this stunning, Cape...

Created Dec 4, 2022

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2 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

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,...

Created Dec 4, 2022

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3 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

A classic Cape home with modern amenities for your comfort, this house is a wonderful home base for your Cape Cod vacation; close to town shops, restaurants and beaches. With a private back yard...

Created Dec 4, 2022

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2 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

Bluestone Haven is a gorgeous new rental home in prestigious East Orleans with modern amenities, a game room, and easy access to all Cape Cod has to offer.We respect our guests autonomy but are...

Created Dec 4, 2022

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3 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

15540 Aqua-Marina: Relax and unwind this summer at our waterfront home on Orleans Cove that accommodates up to seven people. Start your day with an early morning yoga session in the secluded...

Created Dec 4, 2022

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4 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

This is the perfect home for your family get away. Recently remodeled and improved in 2016 with a new kitchen, open floor plan, new master bedroom addition, and new screened porch. Located at the...

Created Dec 4, 2022

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4 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

This a lovely well kept home in East Orleans that sleeps eight very comfortably. It sits on a pretty lot in a quiet neighborhood just 1.8 miles from Nauset Beach. There is a beautiful modern...

Created Dec 4, 2022

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6 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

A 1 minute walk to Nauset Beach, just North of the Public Beach off Callanan's Pass. This vintage Nauset Heights home has a perfect location, nice big yard and outdoor shower. Everything you need...

Created Dec 4, 2022

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4 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

15542: Wake up and head downstairs to a bright sun-drenched kitchen and sunken living area, and relax while sipping your coffee before heading out for a walk to Mill Pond. Or, if you're looking for...

Created Dec 4, 2022

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4 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

You know you are on vacation when you first enter our meticulously maintained bright and comfortably furnished home in South Orleans. Our traditional Cape Cod home has wood floors in most of the...

Created Dec 4, 2022

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Private Vacation Home Vacation Rental In Orleans, Massachusetts

Classic Nauset Heights home sitting directly on the bluff with magnificent views of Nauset Beach, the Atlantic Ocean and Nauset Marsh. Stairs to bay and ocean beaches. Vintage, rustic cottage...

Created Dec 4, 2022

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1 Br Cottage Vacation Rental In Orleans, Massachusetts

*Cancellation policy at end of property description.*If you are looking for a cozy and quiet accommodation on Cape Cod, this cute Orleans cottage in the pines may be the answer! This charming &...

Created Dec 4, 2022

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3 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

Namskaket RetreatOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy quiet privacy and quick access to the...

Created Dec 4, 2022

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4 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

This quintessential Cape Cod home was built in 1775 and has been in the same family for almost 200 years. Charming beyond words this home sits at the end of Tonset Road and looks out over Nauset...

Created Dec 4, 2022

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3 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

Located less than one mile from Pleasant Bay Beach, this well-appointed cape style home is a short drive from many attractions on the lower Cape. Freshwater fishing and swimming enthusiasts will...

Created Dec 4, 2022

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4 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

Beautiful Pleasant Bay waterfront vacation home with 180 degree unobstructed views of the Pleasant Bay estuary. This vacation home is about light-filled rooms virtually all with a view of the...

Created Dec 4, 2022

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3 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

*New deck!**New fire pit with Adirondack chairs!**New outdoor dining table with umbrella!*Thoughtfully designed in keeping with the Cape's historic charm, this beautiful waterfront East Orleans...

Created Dec 4, 2022

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3 Br Cottage Vacation Rental In East Orleans, Massachusetts

Our cottage was originally built in 1941 and has been completely and lovingly restored with vintage white beadboard ceilings, shiplap walls and classic built-ins and has been furnished with...

Created Dec 4, 2022

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3 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

15527 The Lobster Claw: Deeded neighborhood beach access, walking distance to the water, private location, sleeps 6! This charming vacation home, located oceanside in East Orleans, is the perfect...

Created Dec 4, 2022

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5 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

New 2021 Listing! The Harbor View House is perfectly perched privately on a point of land with 180-degree views of salt water. This 4 BR, 2 full and 2 half bath house is a nature lover's paradise...

Created Dec 4, 2022

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3 Br Private Vacation Home Vacation Rental In Orleans, Massachusetts

Listen to the waves from this historic home or walk to Nauset Beach! Home was once part of the Mayo Duck Farm and at one point a restaurant with a huge local following. Now divided into 2 separate...

Created Dec 4, 2022

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