Oceanfront Rentals in Chilmark Chocolates, MA: Compare 10+ Sites & Save

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  2. Oceanfront Rentals
  3.  USA

  4.  Massachusetts

  5.  Chilmark
  6.  Chilmark Chocolates

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69 Best Oceanfront Rentals in Chilmark Chocolates (Starting from $323)

Peaceful Chilmark Farmhouse by Menemsha Beach
Peaceful Chilmark Farmhouse by Menemsha Beach
House
Chilmark, MA, USA
1.8k from Chilmark Chocolates center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms10 Guests
New to Booking
$483
Average price / night
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Pet-Friendly Historic Chilmark House
Pet-Friendly Historic Chilmark House
House
Chilmark, MA, 02535, United States
0.6k from Chilmark Chocolates center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$781
Average price / night
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Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby
Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby
House
Chilmark, MA, 02535, United States
0.8k from Chilmark Chocolates center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

24 reviews

$335
Average price / night
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Private beach compound. Please do not book without contacting the host
Private beach compound. Please do not book without contacting the host
House
Chilmark, MA, 02535, United States
0.9k from Chilmark Chocolates center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms6 Guests
New to Booking
$6680
Average price / night
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Spectacular Newly Renovated Home in Menemsha
Spectacular Newly Renovated Home in Menemsha
House
Chilmark, MA, 02535, United States
1.0k from Chilmark Chocolates center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms10 Guests
10.0

Exceptional

31 reviews

$884
Average price / night
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Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
House
Chilmark, MA, 02535, United States
1.2k from Chilmark Chocolates center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

28 reviews

$409
Average price / night
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Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.
Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.
House
Chilmark, MA, 02535, United States
1.2k from Chilmark Chocolates center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms3 Guests
10.0

Exceptional

57 reviews

$342
Average price / night
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Menemsha Pond waterfront   Available July 18-25, 2026 BOOK NOW!!
Menemsha Pond waterfront Available July 18-25, 2026 BOOK NOW!!
House
Chilmark, MA, 02535, United States
1.4k from Chilmark Chocolates center

Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

5 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$1421
Average price / night
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Stunning Location, Oceanfront Home Chilmark
Stunning Location, Oceanfront Home Chilmark
House
Chilmark, MA, 02535, United States
1.5k from Chilmark Chocolates center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

3 Bedrooms8 Guests
New to Booking
$3654
Average price / night
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Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
House
Chilmark, MA, 02535, United States
1.5k from Chilmark Chocolates center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms8 Guests
8.6

Fabulous

24 reviews

$938
Average price / night
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Classic Vineyard Summer Cottage; Private Waterfront Access; Menemsha Pond Views.
Classic Vineyard Summer Cottage; Private Waterfront Access; Menemsha Pond Views.
Cottage
Chilmark, MA, 02535, United States
1.6k from Chilmark Chocolates center

Dryer, Fireplace, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$584
Average price / night
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Chilmark Home, AC, WiFi, Pet friendly, 2 Tennis ct
Chilmark Home, AC, WiFi, Pet friendly, 2 Tennis ct
House
Chilmark, MA, 02535, United States
1.7k from Chilmark Chocolates center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave

5 Bedrooms12 Guests
New to Booking
$2665
Average price / night
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Menemsha Home Fully Renovated w/ Amazing Waterview's of Vineyard Sound
Menemsha Home Fully Renovated w/ Amazing Waterview's of Vineyard Sound
House
Menemsha, MA, 02535, United States
1.8k from Chilmark Chocolates center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

3 Bedrooms6 Guests
10.0

Exceptional

17 reviews

$741
Average price / night
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Menemsha -   Davis House
Menemsha - Davis House
Cottage
chilmark, MA, 02535, United States
2.1k from Chilmark Chocolates center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom2 Guests
10.0

Exceptional

27 reviews

$323
Average price / night
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Post and Beam home with westward views of the ocean and sunsets
Post and Beam home with westward views of the ocean and sunsets
House
Chilmark, MA, 02535, United States
2.2k from Chilmark Chocolates center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

8 reviews

$1372
Average price / night
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House in Chilmark/Menemsha, Martha's Vineyard w/ Private Beach, Sunset View.
House in Chilmark/Menemsha, Martha's Vineyard w/ Private Beach, Sunset View.
House
Chilmark, MA, 02535, United States
2.2k from Chilmark Chocolates center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

19 reviews

$885
Average price / night
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Bright and cozy menemsha cottage
Bright and cozy menemsha cottage
Cottage
Chilmark, MA, 02535, United States
2.2k from Chilmark Chocolates center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms5 Guests
10.0

Exceptional

5 reviews

$604
Average price / night
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CHILMARK WATERFRONT WITH PRIVATE DOCK
CHILMARK WATERFRONT WITH PRIVATE DOCK
House
Chilmark, MA, 02535, United States
2.3k from Chilmark Chocolates center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
New to Booking
$4073
Average price / night
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Classic  Modern House on its Own Point of Land with Astounding Views
Classic Modern House on its Own Point of Land with Astounding Views
House
Chilmark, MA, 02535, United States
2.4k from Chilmark Chocolates center

Barbecue, Dryer, Fireplace, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

5 Bedrooms11 Guests
10.0

Exceptional

13 reviews

$1144
Average price / night
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Charming Rustic Cottage
Charming Rustic Cottage
Cottage
Chilmark, MA, 02535, United States
2.5k from Chilmark Chocolates center

Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms5 Guests
10.0

Exceptional

9 reviews

$413
Average price / night
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Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!!\n
Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!!\n
House
Chilmark, MA, 02535, United States
2.6k from Chilmark Chocolates center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

26 reviews

$1519
Average price / night
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Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
House
Chilmark, MA, 02535, United States
3.0k from Chilmark Chocolates center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
9.2

Superb

17 reviews

$420
Average price / night
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Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!
Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!
House
Chilmark, MA, 02535, United States
3.0k from Chilmark Chocolates center

Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
9.6

Exceptional

32 reviews

$698
Average price / night
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Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches
Gracious Landmark Home ~ Fabulous Water Views ~ 2 Private Beaches
House
Chilmark, MA, 02535, United States
3.0k from Chilmark Chocolates center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
10.0

Exceptional

25 reviews

$1563
Average price / night
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Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
House
Chilmark, MA, 02535, United States
3.0k from Chilmark Chocolates center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

13 reviews

$929
Average price / night
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Ocean View, Walk to Beach, Dog Friendly
Ocean View, Walk to Beach, Dog Friendly
House
Aquinnah, MA, 02535, United States
3.2k from Chilmark Chocolates center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Heater, Internet, Kitchen

4 Bedrooms9 Guests
New to Booking
$1081
Average price / night
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Walk to private beach from beautiful Abels Hill house
Walk to private beach from beautiful Abels Hill house
House
Chilmark, MA, 02535, United States
3.2k from Chilmark Chocolates center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

6 Bedrooms13 Guests
10.0

Exceptional

35 reviews

$688
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Oceanfront Rentals in Chilmark Chocolates.

Chilmark Chocolates Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 69 verified oceanfront rentals in Chilmark Chocolates. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Chilmark Chocolates vary depending on the property size, exact beachfront location, and season. Rates typically start from around $323 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Chilmark Chocolates offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Chilmark Chocolates welcome pets. Currently, 21 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Chilmark Chocolates often include features designed for a comfortable coastal stay, such as Ocean View, View, and Oceanfront. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.