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Holiday Homes in Chilmark

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Chilmark

Chappy - Family Beach House
Fridge, microwave, oven, stovetop

Chappy - Family Beach House

10.0 out of 10, Exceptional, (14)
"Very nice property. We were comfortable and had everything we needed. "
The price is NZ$1,616
includes taxes & fees
1 Sept - 2 Sept
Chappy - Family Beach House
Newly Renovated Martha's Vineyard Vacation Rental!
Outdoor dining

Newly Renovated Martha's Vineyard Vacation Rental!

9.6 out of 10, Exceptional, (44)
"Love our stay!"
The price is NZ$1,309
includes taxes & fees
4 Sept - 5 Sept
Newly Renovated Martha's Vineyard Vacation Rental!
The Seashell Cove - Martha's Vineyard
Terrace/patio

The Seashell Cove - Martha's Vineyard

9.6 out of 10, Exceptional, (20)
"Property was perfectly kept and very comfortable. "
The price is NZ$2,154
includes taxes & fees
16 Sept - 17 Sept
The Seashell Cove - Martha's Vineyard
The Costal Corner - Martha's Vineyard
Microwave, oven, stovetop, dishwasher

The Costal Corner - Martha's Vineyard

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was great for our golf trip. The 3 bedrooms were exceptional "
The Costal Corner - Martha's Vineyard
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Outdoor dining

Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C

10.0 out of 10, Exceptional, (178)
"The property had all the amenities and features to make guests feel right at home. We appreciated all the details in the decor and we appreciated the suggestions for local restaurants. TheTheviewwdrdreadream!amademade"
The price is NZ$1,494
includes taxes & fees
2 Sept - 3 Sept
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
Marina

Walk to downtown Edgartown in quiet neighborhood - Perfect Location!

10.0 out of 10, Exceptional, (1)
"Katie and Uri were very accommodating! Place was clean, very comfortable and in a good location. We will be back!!"
The price is NZ$1,616
includes taxes & fees
24 Aug - 25 Aug
Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA
Beach

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 NZ$2,075
includes taxes & fees
19 Aug - 20 Aug
Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA
Island Inn - 2 Bedroom & 2 Bath Townhouse - 50G - Oak Bluffs, MA
Beach

Island Inn - 2 Bedroom & 2 Bath Townhouse - 50G - Oak Bluffs, MA

10.0 out of 10, Exceptional, (1)
"Great location, clean, quiet, great amenities inside AND out, loved having special access to Nomans, we were VERY happy with our stay. Thank you for such an awesome option to enjoy MV and Island Life!"
The price is NZ$1,954
includes taxes & fees
28 Aug - 29 Aug
Island Inn - 2 Bedroom & 2 Bath Townhouse - 50G - Oak Bluffs, MA
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA
Beach

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

The price is NZ$1,984
includes taxes & fees
24 Aug - 25 Aug
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA
Island Inn - 2 Bedroom & 2 Bath Townhouse - 48G - Oak Bluffs, MA
Beach

Island Inn - 2 Bedroom & 2 Bath Townhouse - 48G - Oak Bluffs, MA

Island Inn - 2 Bedroom & 2 Bath Townhouse - 48G - Oak Bluffs, MA
Book a Last Minute Cape Escape! Modern, Tranquil Cape home close to town beaches
Smart TV, fireplace

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

10.0 out of 10, Exceptional, (10)
"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 NZ$1,280
includes taxes & fees
17 Sept - 18 Sept
Book a Last Minute Cape Escape! Modern, Tranquil Cape home close to town beaches
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Beach

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

10.0 out of 10, Exceptional, (2)
"Mike & Olya's house is even more beautiful in person, both inside and out.The house is equipped with everything needed for a peaceful stay. The décor and contemporary style made us want to live there — very tasteful.Check-in and check-out were easy to access. We were authorized to enter the house starting at 4 p.m.The cleaning crew was delayed by just a few minutes (maybe 5 minutes), and I immediately received a message saying I had been refunded for the inconvenience. Although such a gesture...
The price is NZ$1,069
includes taxes & fees
17 Sept - 18 Sept
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Exterior detail

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

The price is NZ$1,056
includes taxes & fees
7 Sept - 8 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
TV, fireplace, books

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
The price is NZ$3,397
includes taxes & fees
1 Sept - 2 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Interior

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 NZ$4,035
includes taxes & fees
1 Sept - 2 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Stunning, Classic Renovated Greek Revival - few mins Walk to Main St & VH Ferry
Property grounds

Stunning, Classic Renovated Greek Revival - few mins Walk to Main St & VH Ferry

10.0 out of 10, Exceptional, (41)
"Couldn't have asked for a better place to have as a homebase while I was in town for a wedding! My friends and I loved using the outdoor space and being so close to town. I look forward to coming back for a future vacation. I would highly recommend staying here!"
The price is NZ$3,563
includes taxes & fees
19 Aug - 20 Aug
Stunning, Classic Renovated Greek Revival - few mins Walk to Main St & VH Ferry
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Fridge, microwave, oven, stovetop

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

10.0 out of 10, Exceptional, (12)
"The house is beautiful and conveniently located. The host, Melissa, was accessible and super helpful. We thoroughly enjoyed our time here and hope to be back in the future."
The price is NZ$1,939
includes taxes & fees
15 Sept - 16 Sept
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Charming studio in tranquil Falmouth with AC
Interior

Charming studio in tranquil Falmouth with AC

The price is NZ$319
includes taxes & fees
19 Aug - 20 Aug
Charming studio in tranquil Falmouth with AC
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Exterior detail

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

10.0 out of 10, Exceptional, (29)
"Good location, pretty spot on pond. Nice deck plenty of room for family of 12"
The price is NZ$1,633
includes taxes & fees
14 Sept - 15 Sept
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Cozy Oceanfront Room | 2 Beds + Kitchenette
Beach

Cozy Oceanfront Room | 2 Beds + Kitchenette

The price is NZ$424
includes taxes & fees
1 Sept - 2 Sept
Cozy Oceanfront Room | 2 Beds + Kitchenette
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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Top Chilmark Hotel Reviews

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

10/10 Excellent
"Very nice and clean place. You would never know it from the street view, we were surprised how much we liked the room and the clean sheets and towels. Room had a full fridge, a toaster, a microwave, it was a real studio apartment like. We will be back!"
Kostas 3-night trip
Posted 2 days ago
Vineyard Harbor Motel - Private Beach