Top Winter Vacations - Vacation Rentals in Waskosim's Rock Reservation

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From US $867

         

8.6 (24 Reviews)

House

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

• Parking
• Pool
• TV

• Massachusetts
• Chilmark

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From US $914

         

|

10.0 (1 Review)

House

Hillside Oak

• Pet Friendly
• Wheelchair Accessible
• Balcony/Terrace

• Massachusetts
• Chilmark

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From US $1,403

         

New

House

Chilmark 1-bedroom Bunk house, WiFi, AC. Private Beach, Pets. No kitchen

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chilmark

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From US $563

         

10.0 (17 Reviews)

House

Menemsha Home Fully Renovated w/Amazing Waterview's of Vineyard Sound

• Air Conditioner
• Parking
• TV

• Chilmark
• Menemsha

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From US $1,895

         

|

9.0 (1 Review)

House

The Eliot Noyes

• Pool
• View
• Balcony/Terrace

• Massachusetts
• Chilmark

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From US $1,053

         

10.0 (6 Reviews)

House

Secluded retreat in Seven Gates Farm on 7 Acres, Private Beach, Tennis, Pond

• Vineyard Haven
• West Tisbury

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From US $598

         

10.0 (5 Reviews)

Cottage

Bright and cozy menemsha cottage

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chilmark

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From US $232

         

|

8.6 (6 Reviews)

House

Chilmark Guest House

• Air Conditioner
• Pet Friendly
• Wheelchair Accessible

• Massachusetts
• Chilmark

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From US $773

         

10.0 (57 Reviews)

House

Historic Captains House - Newly Renovated Primary Bathroom and Upgraded Kitchen

• Air Conditioner
• Parking
• TV

• Vineyard Haven
• West Tisbury

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From US $343

         

10.0 (57 Reviews)

House

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chilmark

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From US $410

         

10.0 (28 Reviews)

House

Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chilmark

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From US $1,372

         

10.0 (8 Reviews)

House

Post and Beam home with westward views of the ocean and sunsets

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chilmark

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From US $576

         

10.0 (6 Reviews)

House

Peaceful Chilmark Farmhouse by Menemsha Beach

• Air Conditioner
• Parking
• TV

• Chilmark
• Menemsha

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From US $755

         

10.0 (3 Reviews)

House

The Field House - Peaceful Martha’s Vineyard Escape with Serene Field Views

• Air Conditioner
• Parking
• TV

• Vineyard Haven
• West Tisbury

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From US $802

         

10.0 (1 Review)

House

Peaceful Scenic Up-Island Retreat With Private Martha's Vineyard Beach

• Parking
• Security/Safety
• Bedding/Linens

• Massachusetts
• Chilmark

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From US $1,293

         

9.6 (9 Reviews)

House

Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chilmark

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From US $328

         

9.2 (17 Reviews)

House

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chilmark

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From US $1,514

         

New

House

Amazing sunsets, a welcoming home, and island adventures. Lifetime memories!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chilmark

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From US $527

         

New

Cottage

Cozy 3BR Cottage with Lambert's Cove Beach access

• Air Conditioner
• Parking
• Pet Friendly

• Vineyard Haven
• West Tisbury

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From US $1,169

         

9.6 (35 Reviews)

House

Luminous rural retreat with spectacular ocean views.

• Parking
• Pet Friendly
• TV

• Massachusetts
• Chilmark

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From US $754

         

9.2 (40 Reviews)

House

Striking 5BR/4BA Chilmark Contemporary with Views of the Sound

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chilmark

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From US $622

         

9.8 (11 Reviews)

House

Charming Chilmark beach house with private Abel's Hill beach access

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chilmark

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From US $413

         

10.0 (9 Reviews)

Cottage

Charming Rustic Cottage

• Parking
• TV
• View

• Massachusetts
• Chilmark

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From US $433

         

9.8 (18 Reviews)

House

Peaceful Wooded Retreat, Short Car Ride to Everything. Week is Friday to Friday

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chilmark

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