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Latest Vacation Rentals in Osterville MA (25)

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4 Br Private Vacation Home Vacation Rental In Barnstable, Massachusetts

Stay at this recently renovated 4 bed 3.5 bath Osterville home. Less than a 5 minute walk to Joshua pond ,1 mile from Dowses beach and less than a 10 minute walk to downtown Main Street (0.4 miles...

Created May 12, 2024

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4 Br Private Vacation Home Vacation Rental In Osterville, Massachusetts

Michelle Sylvia high end collection. Introducing the epitome of summer fun in the sun living: Newly unveiled for 2024 in the heart of Osterville. Step into a world of comfort and relaxation in this...

Created May 12, 2024

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6 Br Private Vacation Home Vacation Rental In Osterville, Massachusetts

Originally built in 1886, this home has been a well-loved Wianno area summer home for well over a century. Its proximity to Dowses Beach and Osterville village center make it a very desirable...

Created May 12, 2024

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Private Vacation Home Vacation Rental In Barnstable, Massachusetts

Enjoy a stylish experience at this centrally-located beautifully renovated cape home. It is a five minute walk to Osterville Village and Joshua's Pond (the cleanest and clearest pond in...

Created May 12, 2024

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2 Br Cottage Vacation Rental In Osterville, Massachusetts

Our quaint cottage is located just a minute's walk from Osterville's village center, with its upscale shopping, dining and charming ambiance. It's a quick bike ride or short one-mile drive to the...

Created May 12, 2024

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6 Br Private Vacation Home Vacation Rental In Barnstable, Massachusetts

Welcome to Osterville Seaside Estate, a bright white mansion with ocean views in a highly sought after village on Cape Cod. This grand 1880's estate, steeped in historic charm and beauty, recently...

Created May 12, 2024

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4 Br Private Vacation Home Vacation Rental In Osterville, Massachusetts

4 Bedroom - 2 Baths - Sleeps 8A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of our homes offer flexible stays with a 3 night minimum in the off season -...

Created May 12, 2024

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4 Br Private Vacation Home Vacation Rental In Barnstable, Massachusetts

This home is just a few hundred feet from Nauticus Marina but so private inside and out. Walk to the marina for sunsets over Oyster Harbor or drive a mile to the Village of Osterville for shopping .

Created May 12, 2024

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4 Br Private Vacation Home Vacation Rental In Barnstable, Massachusetts

Amazing summer vacation awaits in this beautiful 4-bedroom Osterville home. Located, on almost an acre, on the private island of Oyster Harbors, a short distance from the town and the beach, you...

Created May 12, 2024

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11 Br Private Vacation Home Vacation Rental In Osterville, Massachusetts

A spacious and welcoming home in a wonderful location. This home allows plenty of room for multi families to vacation together. The large fenced in yard with built in gas fire pit, and inground...

Created May 12, 2024

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3 Br Private Vacation Home Vacation Rental In Osterville, Massachusetts

Summary:21008 - Sun-Kissed Shores: Walk to Joshua Pond Beach & Downtown!The Space:The feeling of a Cape Cod summer doesnt get much better than the beauties of Osterville. With a stunning yet subtle...

Created May 12, 2024

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Private Vacation Home Vacation Rental In Barnstable, Massachusetts

Welcome to this unique home on Micah's Pond in Osterville, Ma. Perfect for a family or 2 couples, this 2+1 bedroom, 3 1/2 bath home and guest cottage is situated on 2.7 private acres. The house...

Created May 12, 2024

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3 Br Private Vacation Home Vacation Rental In Osterville, Massachusetts

Osterville ~Total renovation recently completed and now available for the 2024 rental season. Minimum age to rent is 28.Set on a gorgeous tree-lined street in Osterville this 3 bedroom, 2,900...

Created May 12, 2024

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3 Br Private Vacation Home Vacation Rental In Osterville, Massachusetts

Great Osterville rental for families! Brand new chef's kitchen and bathrooms. Short drive to beach, pond or charming Osterville Village. Rinse off in the outdoor shower, or relax in the spacious...

Created May 12, 2024

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4 Br Private Vacation Home Vacation Rental In Osterville, Massachusetts

Bright, beachy decor and an open floor plan greet you in this centrally located Cape home with countless amenities. Located in the village of Osterville, you will be less than 2 miles from the...

Created May 12, 2024

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3 Br Private Vacation Home Vacation Rental In Osterville, Massachusetts

Welcome to Main Street House - combining history, luxury and location for the perfect Cape Cod vacation home.Main Street House is one of the earliest homes built in idyllic Osterville and is...

Created May 12, 2024

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3 Br Private Vacation Home Vacation Rental In Ostervillle, Massachusetts

Comfortable Family Home in a quiet Osterville neighborhood.Great for your Cape Cod summer vacation.Tastefully updated,offering a fully appliance large kitchen and dining table that will easily sit...

Created May 12, 2024

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4 Br Private Vacation Home Vacation Rental In Barnstable, Massachusetts

This very large beautiful New home in Osterville has everything you need for a fantastic vacation! The home was built in 2004 and has 3300 Square feet on 1.14 Acres. Four very large bedrooms with...

Created May 12, 2024

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4 Br Private Vacation Home Vacation Rental In Osterville, Massachusetts

Michelle Sylvia high end collection. New for 2023! One of the most sought-after streets in all of Osterville. Heated pool, large private yard and fire pit. Close to the beaches of Nantucket Sound...

Created May 12, 2024

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4 Br Private Vacation Home Vacation Rental In Barnstable, Massachusetts

In the heart of historic Osterville village and about a mile to Dowses Beach this is the ideal Cape Cod central Air Conditioned vacation home with a beautiful pool. You are greeted by a bright...

Created May 12, 2024

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5 Br Private Vacation Home Vacation Rental In Barnstable, Massachusetts

Luxury on the Cape. This professionally decorated home in the gated community of Oyster Harbors offers 5 bedrooms, gourmet kitchen, great room, family room, dining room and so much more. Amenities:...

Created May 12, 2024

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4 Br Private Vacation Home Vacation Rental In Barnstable, Massachusetts

Welcome to Starboard Retreat! With its expansive backyard oasis and close proximity to Craigville and Dowses Beaches, this spacious home is a summer paradise for beach goers and pool loungers...

Created May 12, 2024

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3 Br Private Vacation Home Vacation Rental In Barnstable, Massachusetts

Beautiful newly renovated contemporary cape with first floor master bedroom. Beautiful outdoor space with new mahogany deck and stone patio with fire pit. 5 minute walk to village 5 minute drive to...

Created May 12, 2024

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3 Br Private Vacation Home Vacation Rental In Osterville, Massachusetts

Quiet three bedroom, two full bath Cape located on a dead-end street in the quaint town of Osterville.First floor includes master queen bedroom with full bath, second bedroom with two twin beds...

Created May 12, 2024

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4 Br Private Vacation Home Vacation Rental In Barnstable, Massachusetts

Welcome to Seasons by the Sea! Our fully remodeled Cape Cod has 4 bedrooms, 3.5 baths and all the outdoor living spaces you need to have a perfect beach vacation. Located less than a mile from...

Created May 12, 2024

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