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Holiday Homes in Chilmark

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Chilmark

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 AU$994
includes taxes & fees
17 Sept - 18 Sept
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
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 AU$1,518
includes taxes & fees
14 Sept - 15 Sept
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
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 AU$3,160
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 AU$3,751
includes taxes & fees
1 Sept - 2 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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, (11)
"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$1,061
includes taxes & fees
14 Sept - 15 Sept
Book a Last Minute Cape Escape! Modern, Tranquil Cape home close to town beaches
Charming studio in tranquil Falmouth with AC
Interior

Charming studio in tranquil Falmouth with AC

The price is AU$297
includes taxes & fees
31 Aug - 1 Sept
Charming studio in tranquil Falmouth with AC
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Exterior detail

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

The price is AU$983
includes taxes & fees
1 Sept - 2 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
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 AU$1,775
includes taxes & fees
24 Aug - 25 Aug
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA
Cozy Oceanfront Room | 2 Beds + Kitchenette
Beach

Cozy Oceanfront Room | 2 Beds + Kitchenette

The price is AU$395
includes taxes & fees
1 Sept - 2 Sept
Cozy Oceanfront Room | 2 Beds + Kitchenette
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 AU$1,504
includes taxes & fees
1 Sept - 2 Sept
Chappy - Family Beach House
2 Double Bed Oceanview Stay + Shared Deck
1 bedroom, iron/ironing board, WiFi, bed sheets

2 Double Bed Oceanview Stay + Shared Deck

The price is AU$443
includes taxes & fees
4 Sept - 5 Sept
2 Double Bed Oceanview Stay + Shared Deck
Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter!
On the beach, sun-loungers, beach towels

Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter!

10.0 out of 10, Exceptional, (16)
"We had a great stay at Oceans 11! The home is beautiful, it was incredibly clean, and very well stocked! We look forward to staying here again!!"
The price is AU$613
includes taxes & fees
2 Sept - 3 Sept
Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter!
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 AU$1,153
includes taxes & fees
4 Sept - 5 Sept
Newly Renovated Martha's Vineyard Vacation Rental!
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, (13)
"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 AU$1,805
includes taxes & fees
21 Sept - 22 Sept
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
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 AU$1,388
includes taxes & fees
2 Sept - 3 Sept
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Elisa's Cottage - Your Family Vacation Destination
Fridge, microwave, oven, stovetop

Elisa's Cottage - Your Family Vacation Destination

10.0 out of 10, Exceptional, (6)
"We enjoyed the proximity to Woods Hole and Falmouth and the added snack touches. "
The price is AU$1,429
includes taxes & fees
26 Aug - 27 Aug
Elisa's Cottage - Your Family Vacation Destination
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Fridge, microwave, oven, stovetop

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10.0 out of 10, Exceptional, (198)
"As always, lovely home. Perfect place."
The price is AU$924
includes taxes & fees
11 Sept - 12 Sept
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Stones Throw Waterfront
Terrace/patio

Stones Throw Waterfront

8.4 out of 10, Very good, (5)
"We've selected this place for two main reasons - 1) Kayaks included, and 2) pets are welcome (at least, a dog - check the rules). Apart from the two kayaks, three standup boards (SUB) were also available. The property is located near a small cove, so it's perfect for SUB beginners, as there are no waves due to power motorboats, jet skis, etc. Note that launching the boats ISN'T a walk in the park. You'll have to deal with a narrow and relatively steep path, dealing with shrubs, rocks, and...
The price is AU$1,199
includes taxes & fees
24 Aug - 25 Aug
Stones Throw Waterfront
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 AU$1,504
includes taxes & fees
24 Aug - 25 Aug
Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
4 bedrooms, desk, iron/ironing board, travel cot

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

10.0 out of 10, Exceptional, (12)
"We so enjoyed our stay! Alexis has thought of everything to make a visit comfortable. Enjoyed the location and was able to walk to the village for coffee! Very convenient location and would highly recommend!"
The price is AU$2,275
includes taxes & fees
16 Sept - 17 Sept
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
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

Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"Greeted by front desk upon entering the hotel. Room was clean "
Nancy 1-night trip
Posted 23 hours ago
Iris Hotel Cape Cod