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
Save 100% on your flight
Price was $1,324, price is now $877 per person
$877
per person
Aug 28 - Sep 1
found 4 hours ago
Roundtrip non-stop flight included
Miami (MIA) 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.
Morgan Hotel

Morgan Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,809, price is now $1,316 per person
$1,316
per person
Aug 28 - Sep 1
found 4 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Vineyard Haven (MVY)
This hotel features free WiFi in public areas, luggage storage, and concierge services.
The Richard, The Edgartown Collection

The Richard, The Edgartown Collection

3.5 out of 5
Save 100% on your flight
Price was $2,127, price is now $1,596 per person
$1,596
per person
Aug 28 - Sep 1
found 4 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Vineyard Haven (MVY)
This hotel features free WiFi in public areas, concierge services, and self parking. Enjoy the free self-serve breakfast each morning. A terrace, a garden, and express check-out are also on offer.
The Sydney, The Edgartown Collection

The Sydney, The Edgartown Collection

3.5 out of 5
Save 100% on your flight
Price was $2,796, price is now $2,266 per person
$2,266
per person
Aug 28 - Sep 1
found 4 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Vineyard Haven (MVY)
This hotel features self parking and free WiFi in public areas. Enjoy the free self-serve breakfast each morning. Express check-out is also provided.
The Edgartown Inn, The Edgartown Collection

The Edgartown Inn, The Edgartown Collection

3.5 out of 5
Save 100% on your flight
Price was $2,640, price is now $2,143 per person
$2,143
per person
Aug 28 - Sep 1
found 4 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Vineyard Haven (MVY)
Free WiFi in public areas, a terrace, and express check-out are available at this hotel. Enjoy the free self-serve breakfast each morning. Concierge services are provided for your convenience.

Top Chilmark hotels deals

Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool

Chilmark MA
Get rates
An outdoor pool is featured at this apartment, along with barbecue grills.
Pool
Kitchen
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
$242 nightly
The price is $277 total per night
$277 total
Jul 19 - Jul 20
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
Parking included
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd North Falmouth MA
$443 nightly
The price is $507 total per night
$507 total
Jul 9 - Jul 10
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
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
60 Beach Road Vineyard Haven MA
$257 nightly
The price is $287 total per night
$287 total
Jul 21 - Jul 22
Total with taxes and fees
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.
On private beach
Parking included
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street Falmouth MA
Free Cancellation
Reserve now, pay when you stay
$158 nightly
The price is $178 total per night
$178 total
Jul 15 - Jul 16
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
$476 nightly
The price is $532 total per night
$532 total
Jul 12 - Jul 13
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 $877. 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.