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Chilmark Vacation Rentals

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Vacation Rentals in Chilmark

Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach

10.0 out of 10, Exceptional, (29)
"We loved our stay here. It is a private and peaceful location. Christian was a great and responsive host. The house was exactly as listed and very comfortable and clean."
The price is CA $679
CA $1,518 total
includes taxes & fees
Jul 29 - Jul 30
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach

The Seashell Cove - Martha's Vineyard

9.6 out of 10, Exceptional, (18)
"My family and I had a great stay in this lovely home!! The house had everything we needed and was a great starting point for all island adventures. Charles was so helpful throughout the entire trip. We would most certainly stay here again!"
The price is CA $1,135
CA $1,794 total
includes taxes & fees
Jul 7 - Jul 8
The Seashell Cove - Martha's Vineyard

Popponesset, Exclusive, 3-Bdrm, 4-Bths, heated pool, hot tub, firepit, and A/C

10.0 out of 10, Exceptional, (75)
"Loved the house. Enjoyed our walk to the beach "
The price is CA $2,046
CA $3,209 total
includes taxes & fees
Jul 26 - Jul 27
Popponesset, Exclusive, 3-Bdrm, 4-Bths, heated pool, hot tub, firepit, and A/C

STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME

2.0 star property
10.0 out of 10, Exceptional, (10)
"This beach town home is elegant and charming. The location is unbeatable; we enjoyed easy access to the beach, as well as nearby shops and restaurants. We spent our days beaching it up, and exploring the local area (all fun stuff within walking distance). From the moment we booked to the day we departed, the host always had prompt, friendly and helpful communication, and provided us with great recommendations for things to do for the whole family. THANK YOU FOR AN UNFORGETTABLE vacation, we just...
The price is CA $983
CA $1,590 total
includes taxes & fees
Jul 6 - Jul 7
STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME

New Rental-2 bedrm, 1.5 baths in Maushop Village, private beach

10.0 out of 10, Exceptional, (2)
"Great place to stay was very clean. Beautiful location, could see the ocean from the balcony in the bedroom. Beach was only a few steps away from the house. would definitely book again."
The price is CA $781
CA $1,625 total
includes taxes & fees
Jul 11 - Jul 12
New Rental-2 bedrm, 1.5 baths in Maushop Village, private beach

Walk to Edgartown Wharf - Upgraded Vineyard Home with A/C and Outdoor Area

10.0 out of 10, Exceptional, (48)
"We absolutely loved staying here. Great location, perfect size for us. Very clean and had everything we needed."
The price is CA $1,223
CA $1,988 total
includes taxes & fees
Jul 8 - Jul 9
Walk to Edgartown Wharf - Upgraded Vineyard Home with A/C and Outdoor Area

Centrally-Located New Seabury Waterfront: Last Summer Week at -35% August 23-29!

10.0 out of 10, Exceptional, (124)
"Very nice and would stay there again"
The price is CA $1,155
CA $2,211 total
includes taxes & fees
Jul 19 - Jul 20
Centrally-Located New Seabury Waterfront: Last Summer Week at -35% August 23-29!

NEW! Edgartown 3 BR 2 Bath Newly Remodeled Home

10.0 out of 10, Exceptional, (16)
"House was clean and comfortable. Particularly appreciated the childproofing and children’s play area in the back."
The price is CA $1,365
CA $2,321 total
includes taxes & fees
Jul 5 - Jul 6
NEW! Edgartown 3 BR 2 Bath Newly Remodeled Home

Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA

8.0 out of 10, Very good, (1)
The price is CA $781
CA $1,170 total
includes taxes & fees
Jul 20 - Jul 21
Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA

Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA

The price is CA $707
CA $1,076 total
includes taxes & fees
Jul 6 - Jul 7
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA

Island Inn - 2 Bedroom & 2 Bath Townhouse - 49G - Oak Bluffs, MA

The price is CA $798
CA $1,191 total
includes taxes & fees
Jul 10 - Jul 11
Island Inn - 2 Bedroom & 2 Bath Townhouse - 49G - Oak Bluffs, MA

Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 46G - Oak Bluffs, MA

The price is CA $1,054
CA $1,519 total
includes taxes & fees
Jul 30 - Jul 31
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 46G - Oak Bluffs, MA

Island Inn - 2 Bedroom & 2 Bath Townhouse - 42G - Dog-friendly - Oak Bluffs, MA

The price is CA $1,250
CA $1,768 total
includes taxes & fees
Aug 3 - Aug 4
Island Inn - 2 Bedroom & 2 Bath Townhouse - 42G - Dog-friendly - Oak Bluffs, MA

Book a Last Minute Cape Escape! Modern, Tranquil Cape home close to town beaches

10.0 out of 10, Exceptional, (8)
"We very much enjoyed the stay and wowed by the beautiful decoration of the house. The owners take good care of this house and they are also very approachable. Thank you for providing such a wonderful environment for our vacation!"
The price is CA $661
CA $1,303 total
includes taxes & fees
Jul 8 - Jul 9
Book a Last Minute Cape Escape! Modern, Tranquil Cape home close to town beaches

Cape Cod Waterfront Retreat with Dock

10.0 out of 10, Exceptional, (1)
"We had a family emergency and needed a home that accommodated our large family. This home was perfect for us; clean, great location and plenty of space for everyone. The property management team was fantastic in accommodating our needs on short notice and was quick to respond to our questions. "
The price is CA $2,920
CA $4,457 total
includes taxes & fees
Jul 27 - Jul 28
Cape Cod Waterfront Retreat with Dock

Spacious home for entertaining, centrally located to beach, ferry, and airport.

10.0 out of 10, Exceptional, (3)
"A little problem with oven which seemed to run cooler than set temperature. Everything else was fantastic."
The price is CA $3,668
CA $6,177 total
includes taxes & fees
Jul 27 - Jul 28
Spacious home for entertaining, centrally located to beach, ferry, and airport.

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
The price is CA $2,649
CA $4,022 total
includes taxes & fees
Jul 7 - Jul 8
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Spring Escape in Hatchville – Sleeps 6 + Dogs!

10.0 out of 10, Exceptional, (9)
"Great house, renovates 10 minutes to everything and the game barn is fun for families. "
The price is CA $713
CA $1,420 total
includes taxes & fees
Jul 21 - Jul 22
Spring Escape in Hatchville – Sleeps 6 + Dogs!

AMAZING Location! Hottub! Walk 2 beach! Slps 9

2.0 star property
10.0 out of 10, Exceptional, (10)
"Very happy with our stay and definitely would rebook again in the future. "
The price is CA $1,359
CA $2,617 total
includes taxes & fees
Jul 24 - Jul 25
AMAZING Location! Hottub! Walk 2 beach! Slps 9

Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

10.0 out of 10, Exceptional, (28)
"Good location, pretty spot on pond. Nice deck plenty of room for family of 12"
The price is CA $679
CA $1,950 total
includes taxes & fees
Aug 2 - Aug 3
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

Can I find vacation rentals in Chilmark?

Yes, there are vacation rentals in Chilmark near Chilmark Chocolates, or you can select a more secluded option if you're looking for extra privacy while you relax. Chilmark is known for its beaches and wineries. Make sure you have time to check out the festivals and local tours during your trip.

What are some of the best vacation rentals that Chilmark has to offer?

Water-view home in great location with spacious backyard, grill, kayaks, dogs OK: This highly rated vacation home rental in Chilmark offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Chilmark?

Choose from 68 Expedia vacation rentals in Chilmark for a memorable vacation.

What’s there to see and do in Chilmark?

Family-friendly attractions include Chilmark Chocolates and Fulling Mill Brook Preserve, whereas Menemsha Beach and Lucy Vincent Beach are a couple of great spots to enjoy the outdoors. While here, Chilmark Town Hall and Chilmark Public Library are other places worth a visit.

What’s a vacation rental in Chilmark like?

A vacation rental is a private property where you can stay for a long or short time in Chilmark. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.