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Chilmark Holiday Rentals

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Check prices for these dates

Tonight
15 July - 16 July
Tomorrow
16 July - 17 July
This weekend
18 July - 20 July
Next weekend
25 July - 27 July

Holiday Rentals in Chilmark

Chilmark 1-bedroom Bunk house, WiFi, AC. Private Beach, Pets. No kitchen
1 bedroom, WiFi, bed sheets

Chilmark 1-bedroom Bunk house, WiFi, AC. Private Beach, Pets. No kitchen

The price is AU$2,188
includes taxes & fees
16 July - 17 July
Chilmark 1-bedroom Bunk house, WiFi, AC. Private Beach, Pets. No kitchen
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
Enjoy the serene atmosphere on this elevated deck, surrounded by lush trees and grass, with a bench and staircase.

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

10.0 out of 10, Exceptional, (31)
"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 AU$1,609
includes taxes & fees
29 July - 30 July
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
The Seashell Cove - Martha's Vineyard
Enjoy outdoor leisure on the spacious deck with a table and chairs.

The Seashell Cove - Martha's Vineyard

9.6 out of 10, Exceptional, (19)
"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 AU$3,292
includes taxes & fees
21 July - 22 July
The Seashell Cove - Martha's Vineyard
The Costal Corner - Martha's Vineyard
Enjoy cooking and dining in this well-equipped kitchen with a central island, ample counter space, and integrated appliances.

The Costal Corner - Martha's Vineyard

2.0 star property
The price is AU$3,533
includes taxes & fees
9 Aug - 10 Aug
The Costal Corner - Martha's Vineyard
Popponesset, Exclusive, 3-Bdrm, 4-Bths, heated pool, hot tub, firepit, and A/C
Relax in this stylish living area with a large sofa, coffee table, and console table.

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

10.0 out of 10, Exceptional, (76)
"Loved the house. Enjoyed our walk to the beach "
The price is AU$4,441
includes taxes & fees
26 July - 27 July
Popponesset, Exclusive, 3-Bdrm, 4-Bths, heated pool, hot tub, firepit, and A/C
Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
Waterfront homes line the tranquil shore, offering a picturesque setting for a relaxing getaway.

Walk to downtown Edgartown in quiet neighborhood - Perfect Location!

The price is AU$2,268
includes taxes & fees
9 Aug - 10 Aug
Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME
Overlooking the ocean, this property features a white wall along the beach.

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...
STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME
New Rental-Maushop Village, 2-bedroom, 1.5 baths, A/C, patios & private beach
Property grounds

New Rental-Maushop Village, 2-bedroom, 1.5 baths, A/C, patios & private beach

10.0 out of 10, Exceptional, (1)
"We loved our vacation! The house is adorable and decorated with cute beach decorations...the neighborhood is pretty and the people are very kind. Its Mashpee commons are close by for fun shopping and restaurants. We would absolutely recommend and come back again !"
The price is AU$1,545
includes taxes & fees
17 July - 18 July
New Rental-Maushop Village, 2-bedroom, 1.5 baths, A/C, patios & private beach
Centrally-Located New Seabury Waterfront: Rare One Summer Night Open July 19!
Guests can enjoy serene lakeside views from a spacious deck with comfortable seating.

Centrally-Located New Seabury Waterfront: Rare One Summer Night Open July 19!

10.0 out of 10, Exceptional, (124)
"Very nice and would stay there again"
The price is AU$2,257
includes taxes & fees
19 July - 20 July
Centrally-Located New Seabury Waterfront: Rare One Summer Night Open July 19!
Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA
Enjoy a serene beach experience with a tranquil sea view and a scenic pier extending into the calm waters.

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

9.0 out of 10, Wonderful, (2)
"Great location. Very nice property. The unit was clean but dated in a few areas. Overall, it was perfect for 4 of us visiting for the wknd. "
The price is AU$1,672
includes taxes & fees
20 July - 21 July
Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA
Island Inn - 2 Bedroom & 2 Bath Townhouse - 47G - Oak Bluffs, MA
Enjoy the serene coastal views from a natural breakwater, with a small pier or viewing platform nearby.

Island Inn - 2 Bedroom & 2 Bath Townhouse - 47G - Oak Bluffs, MA

10.0 out of 10, Exceptional, (2)
"Property was clean and very accomaditing "
The price is AU$1,465
includes taxes & fees
31 July - 1 Aug
Island Inn - 2 Bedroom & 2 Bath Townhouse - 47G - Oak Bluffs, MA
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA
Enjoy a serene beach experience with a rocky breakwater extending into the calm sea.

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

The price is AU$1,711
includes taxes & fees
28 July - 29 July
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA
Island Inn - 2 Bedroom & 2 Bath Townhouse - 42G - Dog-friendly - Oak Bluffs, MA
Enjoy a serene beachside stroll along the breakwater, surrounded by the soothing sounds of the calm sea.

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

Island Inn - 2 Bedroom & 2 Bath Townhouse - 42G - Dog-friendly - Oak Bluffs, MA
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 46G - Oak Bluffs, MA
Walk along the beach and enjoy the tranquil atmosphere.

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

The price is AU$1,729
includes taxes & fees
30 July - 31 July
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 46G - Oak Bluffs, MA
Book a Last Minute Cape Escape! Modern, Tranquil Cape home close to town beaches
Relax in this spacious living room with a central seating area featuring two sofas and two armchairs.

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 AU$1,298
includes taxes & fees
29 July - 30 July
Book a Last Minute Cape Escape! Modern, Tranquil Cape home close to town beaches
Cape Cod Waterfront Retreat with Dock
Enjoy the serene coastal views and beach access.

Cape Cod Waterfront Retreat with Dock

10.0 out of 10, Exceptional, (2)
"A terrific property that was top-end from all perspectives. It was clean, spacious, modern and homey. Had a great backyard and plenty of room inside and out to relax alone or with friends and family. We loved the location and will absolutely come back. Thank you!"
Cape Cod Waterfront Retreat with Dock
Spacious home for entertaining, centrally located to beach, ferry, and airport.
Enjoy cooking in this well-equipped kitchen with a large island, appliances, and ample storage.

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 AU$6,934
includes taxes & fees
27 July - 28 July
Spacious home for entertaining, centrally located to beach, ferry, and airport.
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Staircase leads to an upper level, with a kitchen area and modern appliances in the background.

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 AU$4,551
includes taxes & fees
16 July - 17 July
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Pet Friendly Cape Cod Home for your Fall Getaway! Minutes to Golf & Beaches!
Enjoy cooking in this well-equipped kitchen with a central island, sink, and dishwasher.

Pet Friendly Cape Cod Home for your Fall Getaway! Minutes to Golf & Beaches!

9.6 out of 10, Exceptional, (7)
"Wonderful home for a family stay, enjoyed area beaches and restaurants. Everything we could of needed was there to use!"
Pet Friendly Cape Cod Home for your Fall Getaway! Minutes to Golf & Beaches!
Spring Escape in Hatchville – Sleeps 6 + Dogs!
Enjoy a game of ping pong or foosball in this lively indoor space.

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 AU$1,612
includes taxes & fees
27 July - 28 July
Spring Escape in Hatchville – Sleeps 6 + Dogs!
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 holiday rentals in Chilmark?

Yes, there are holiday rentals in Chilmark close to Chilmark Chocolates, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Chilmark has to offer?

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.: This highly rated holiday home rental in Chilmark is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 1 hot tub. Our travellers also rate Water-view home in great location with spacious backyard, grill, kayaks, dogs OK as a favourite home for rent in Chilmark.

How many holiday rentals are there in Chilmark?

Choose from 70 Expedia holiday rentals in Chilmark for a memorable holiday.

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 holiday rental in Chilmark like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chilmark. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.