Top Winter Vacations - Vacation Rentals in The Yard

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From US $985

         

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 $667

         

10.0 (5 Reviews)

Cottage

Bright and cozy menemsha cottage

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chilmark

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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 $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 $232

         

|

8.6 (6 Reviews)

House

Chilmark Guest House

• Air Conditioner
• Pet Friendly
• Wheelchair Accessible

• Massachusetts
• Chilmark

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From US $417

         

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 $483

         

|

New

House

Peaceful Chilmark Farmhouse by Menemsha Beach

• Parking
• View
• Ocean View

• Chilmark
• Menemsha

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From US $451

         

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 $1,271

         

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 $573

         

10.0 (6 Reviews)

House

Peaceful Chilmark Farmhouse by Menemsha Beach

• Air Conditioner
• Parking
• TV

• Chilmark
• Menemsha

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From US $651

         

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 $1,233

         

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 $335

         

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 $5,940

         

New

House

2 BR, Modern Main House, 1000 feet of private beach, AC, WiFi, Gym

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Massachusetts
• Chilmark

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From US $1,436

         

New

House

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

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chilmark

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From US $1,155

         

New

House

Spacious and gracious architect designed home on 3 acres off Middle Road.

• 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 $734

         

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 $447

         

10.0 (9 Reviews)

Cottage

Charming Rustic Cottage

• Parking
• TV
• View

• Massachusetts
• Chilmark

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★ Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in The Yard.