Short-Term Rentals in Chilmark Chocolates, MA: Compare 10+ Sites & Save

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108 Best Short-Term Rentals in Chilmark Chocolates (Starting from $143)

The Eliot Noyes
The Eliot Noyes
House
Chilmark, MA, USA
1.5k from Chilmark Chocolates center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

4 Bedrooms8 Guests
8.5

Very Good

2 reviews

$1895
Average price / night
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Pet-Friendly Historic Chilmark Cottage
Pet-Friendly Historic Chilmark Cottage
Cottage
Chilmark, MA, 02535, United States
0.6k from Chilmark Chocolates center

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

3 Bedrooms5 Guests
9.6

Exceptional

12 reviews

$480
Average price / night
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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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Wayside Camp
Wayside Camp
House
Chilmark, MA, USA
1.9k from Chilmark Chocolates center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

3 Bedrooms6 Guests
3.0

Review score

1 reviews

$637
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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Chilmark Guest House
Chilmark Guest House
House
Chilmark, MA, USA
3.0k from Chilmark Chocolates center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family

2 Bedrooms4 Guests
8.6

Fabulous

5 reviews

$232
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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Hillside Oak
Hillside Oak
House
Chilmark, MA, USA
3.2k from Chilmark Chocolates center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$914
Average price / night
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Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice
Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice
House
Chilmark, MA, 02535, United States
1.0k from Chilmark Chocolates center

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

4 Bedrooms8 Guests
10.0

Exceptional

52 reviews

$780
Average price / night
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Beachroad Hideout
Beachroad Hideout
House
Lobsterville, MA, USA
4.4k from Chilmark Chocolates center

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

3 Bedrooms7 Guests
5.0

Review score

2 reviews

$830
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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Lobsterville Landing
Lobsterville Landing
House
Lobsterville, MA, USA
4.4k from Chilmark Chocolates center

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

3 Bedrooms6 Guests
New to Booking
$640
Average price / night
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Quintessential Chilmark Retreat - Marthas Vineyard
Quintessential Chilmark Retreat - Marthas Vineyard
House
Chilmark, MA, 02535, United States
1.1k from Chilmark Chocolates center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, No Smoking, TV

3 Bedrooms8 Guests
9.8

Exceptional

15 reviews

$909
Average price / night
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Bijha's View
Bijha's View
House
Chilmark, MA, USA
5.9k from Chilmark Chocolates center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$143
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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C-Haven
C-Haven
House
West Tisbury, MA, USA
9.1k from Chilmark Chocolates center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
8.0

Good

1 reviews

$349
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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2-bedroom cottage in Chilmark 1/2 mile from Menemsha Harbor and fishing village
2-bedroom cottage in Chilmark 1/2 mile from Menemsha Harbor and fishing village
Cottage
Chilmark, MA, 02535, United States
1.8k from Chilmark Chocolates center

AC, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, No Smoking, Outdoor Space, TV

2 Bedrooms4 Guests
New to Booking
$357
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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Vintage 1920s House W/Beach Path & Glorious Sunset Water Views
Vintage 1920s House W/Beach Path & Glorious Sunset Water Views
House
Chilmark, MA, 02535, United States
2.1k from Chilmark Chocolates center

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

3 Bedrooms8 Guests
10.0

Exceptional

28 reviews

$503
Average price / night
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Tilton House - Menemsha Harborside
Tilton House - Menemsha Harborside
House
Chilmark, MA, 02535, United States
2.1k from Chilmark Chocolates center

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

2 Bedrooms4 Guests
10.0

Exceptional

8 reviews

$390
Average price / night
Check Availability

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 Short-Term Rentals in Chilmark Chocolates.

Chilmark Chocolates Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 108 verified short-term rentals in Chilmark Chocolates, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Chilmark Chocolates vary depending on location, property size, and travel dates. Rates typically start from around $143 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Chilmark Chocolates include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Chilmark Chocolates, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Chilmark Chocolates often include amenities such as Laundry, Fireplace/Heating, and Balcony/Terrace, providing a comfortable and convenient stay.

Short-term rentals in Chilmark Chocolates are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.