Deals on vacations and trips to Chilmark

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Price found within the past 48 hours. Click for updated prices.
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
Price was $1,270, price is now $1,192 per person
$1,192
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
Charleston (CHS) to Vineyard Haven (MVY)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a picnic area, and luggage storage are also on offer.
Harbor View Hotel

Harbor View Hotel

5 out of 5
Price was $1,519, price is now $1,357 per person
$1,357
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
Charleston (CHS) to Vineyard Haven (MVY)
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and free valet parking. Enjoy the seasonal outdoor pool and perks like free self parking.
The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
Price was $1,394, price is now $1,273 per person
$1,273
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
Charleston (CHS) to Vineyard Haven (MVY)
This resort's 3 outdoor tennis courts and seasonal outdoor pool are among the featured amenities. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free beach shuttle. A garden, a picnic area, and laundry facilities are also on offer.
The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
Price was $1,368, price is now $1,302 per person
$1,302
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
Charleston (CHS) to Vineyard Haven (MVY)
Luggage storage is available at this hotel. Take advantage of the free self parking.
Faraway Martha's Vineyard

Faraway Martha's Vineyard

4 out of 5
Price was $1,427, price is now $1,389 per person
$1,389
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
Charleston (CHS) to Vineyard Haven (MVY)
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.

Top Chilmark hotels deals

Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool

Chilmark MA
$480 nightly
The price is $536 total per night
$536 total
Sep 28 - Sep 29
Total with taxes and fees
An outdoor pool is featured at this apartment, along with barbecue grills.
Pool
Kitchen
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd North Falmouth MA
$216 nightly
The price is $248 total per night
$248 total
Oct 22 - Oct 23
Total with taxes and fees
A private beach, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the picnic area.
On private beach
Pool
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd Falmouth MA
Free Cancellation
Reserve now, pay when you stay
$133 nightly
The price is $152 total per night
$152 total
Oct 12 - Oct 13
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Inn on the Square

Inn on the Square

3.5 out of 5
40 North Main Street Falmouth MA
Free Cancellation
Reserve now, pay when you stay
$128 nightly
The price is $147 total per night
$147 total
Oct 22 - Oct 23
Total with taxes and fees
A restaurant and an indoor pool are featured at this hotel. WiFi in public areas is free. A garden is provided and the front desk is staffed around-the-clock.
Pool
Free WiFi
Faraway Martha's Vineyard

Faraway Martha's Vineyard

4 out of 5
23 Kelly Street Edgartown MA
$307 nightly
The price is $343 total per night
$343 total
Oct 18 - Oct 19
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.
Pool
Pet friendly
Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
$170 nightly
The price is $190 total per night
$190 total
Oct 13 - Oct 14
Total with taxes and fees
This hotel features free WiFi in public areas, concierge services, and self parking. A snack bar/deli and luggage storage are also provided.
Free WiFi
Air conditioning
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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.

Stay near popular Chilmark attractions

Menemsha Beach

Why not spend a carefree afternoon at Menemsha Beach during your travels in Chilmark? Take in the festivals and sunsets in the area.
See properties

Frequently asked questions

How much are vacation packages to Chilmark?
You can find an excellent flight and hotel bundle for as little as $1,192. With one of our Travelocity vacation packages, a getaway in Chilmark has never looked more irresistible! Save your time and cash and then start packing that suitcase.
How long should my Chilmark vacation be?
Many visitors pack their suitcase and explore the sights of Chilmark for an average of 2 nights. That's a good starting point, but don't feel limited by it. Whether you stay for a couple of days to see the major sights or hang around to uncover hidden treasures, an unforgettable journey awaits.
Where can I get the best vacation package deals for Chilmark?
It's hard to beat Travelocity when it comes to crafting your Chilmark package deal. There are at least 400 air carriers and 1,000,000 worldwide properties to select from. Secure your trip now and get ready to cross another amazing place off your to-do list.
Why should I purchase my Chilmark vacation package with Travelocity?
Travel is all about making fantastic new memories and leaving all your stresses behind — which is why we provide you with a friendly team of customer service experts on hand around-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our terrific range of destinations. So what are you waiting for? There's no time like the present to secure that vacation you've always dreamed of.
Can I save money on my Chilmark car rental if I book it with a hotel or flight?
You sure can — combine your hotel, flight and car into a Chilmark vacation package and you'll save tons. With so much to discover in and around Chilmark, having your own wheels will make exploring a joy. Once you've buckled yourself in, crank up the tunes and find your way to Fenway Park, a famous attraction roughly 70 mi from Chilmark.
Which airport is best for Chilmark?
For many people, heading to Chilmark means a visit to T.F. Green Airport (PVD). This bustling airport is situated 45 mi northwest of the downtown area. You could also fly into Martha's Vineyard Airport (MVY) (8 mi away from central Chilmark) or Nantucket Memorial Airport (ACK) (35 mi away from central Chilmark).
What is there to do in Chilmark?
Chilmark is teeming with things to see and do, including Lucy Vincent Beach and The Yard. These two fantastic attractions top most tourists' to-do lists.
Where should I stay when visiting Chilmark?
The Menemsha Inn & Cottages is popular with many visitors. Book soon before it's too late.

Photos of local treasures

Browse Chilmark vacation photos for more inspiration

A dock with boats, a small wooden structure, and a forested shoreline.
A beach with large rock formations and the ocean in the background.
A sunset over a calm sea with a rocky shoreline and a distant buoy.
A coastal landscape with a lighthouse, cliffs, and the ocean.
A building with a red door and a white fish sign.