Old Mansions - Vacation Rentals in Chilmark Chocolates

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From US $492

         

10.0 (87 Reviews)

House

Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Aquinnah

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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 $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 $1,895

         

|

9.0 (1 Review)

House

The Eliot Noyes

• Pool
• View
• Balcony/Terrace

• 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 $232

         

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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 $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 $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 $460

         

9.6 (21 Reviews)

Apartment

Cozy efficiency apartment/heated pool

• Air Conditioner
• Parking
• Pool

• 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 $560

         

5.8 (7 Reviews)

House

Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach

• Air Conditioner
• Parking
• TV

• Massachusetts
• Aquinnah

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From US $1,955

         

New

House

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

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chilmark

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From US $1,205

         

New

House

Beautiful Aquinnah Home: Ocean View, Walk to Beach

• Air Conditioner
• Pet Friendly
• TV

• Massachusetts
• Aquinnah

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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 $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 $1,564

         

10.0 (25 Reviews)

House

Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches

• Air Conditioner
• Parking
• Pet Friendly

• 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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From US $1,085

         

10.0 (26 Reviews)

House

Cool, Mid-Century House - Lucy Vincent Beach and Pool!n

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Chilmark

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★ Pro Tip: Old Mansions makes it easy to compare the best listings on Old Mansions homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Old Mansions 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 Chilmark Chocolates.