Deals on vacations and trips to Chilmark

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Chilmark flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Morgan Hotel

Morgan Hotel

2.5 out of 5
Price was $781, price is now $698 per person
$698
per person
Mar 22 - Mar 27
found 1 hour ago
Roundtrip flight included
Washington (DCA) to Vineyard Haven (MVY)
This hotel features free WiFi in public areas, luggage storage, and concierge services.
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
Price was $844, price is now $751 per person
$751
per person
Mar 22 - Mar 27
found 1 hour ago
Roundtrip flight included
Washington (DCA) to Vineyard Haven (MVY)
This motel features a terrace, laundry facilities, and free self parking. A picnic area, luggage storage, and barbecue grills are also on offer.
The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
Price was $1,325, price is now $1,199 per person
$1,199
per person
Mar 22 - Mar 27
found 1 hour ago
Roundtrip flight included
Washington (DCA) 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 Christopher, The Edgartown Collection

The Christopher, The Edgartown Collection

3 out of 5
Price was $2,060, price is now $1,901 per person
$1,901
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Birmingham (BHM) to Vineyard Haven (MVY)
Free WiFi in public areas, a terrace, and a garden are available at this bed & breakfast. Enjoy the free self-serve breakfast each morning. A communal living room and express check-out are also provided.
The Coco, The Edgartown Collection

The Coco, The Edgartown Collection

3 out of 5
Price was $2,044, price is now $1,932 per person
$1,932
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Birmingham (BHM) to Vineyard Haven (MVY)
A restaurant, self parking, and a terrace are among this inn's amenities. Guests will appreciate free perks like self-serve breakfast and WiFi in public areas. A communal living room is also provided.

Top Chilmark hotels deals

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
$131 nightly
The price is $150 total per night
$150 total
Feb 22 - Feb 23
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.
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street Falmouth MA
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $137 total per night
$137 total
Mar 1 - Mar 2
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
Harbor View Hotel

Harbor View Hotel

5 out of 5
131 N Water Street Marthas Vineyard Edgartown MA
$243 nightly
The price is $271 total per night
$271 total
Feb 22 - Feb 23
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. Enjoy the seasonal outdoor pool and perks like free self parking.
Pool
Pet friendly
Faraway Martha's Vineyard

Faraway Martha's Vineyard

3.5 out of 5
23 Kelly Street Edgartown MA
Get rates
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
Mansion House Inn And Spa

Mansion House Inn And Spa

3.5 out of 5
9 Main Street Vineyard Haven MA
$189 nightly
The price is $209 total per night
$209 total
Feb 22 - Feb 23
Total with taxes and fees
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Business travelers can take advantage of the business center. There's an indoor pool on site, and a rooftop terrace and a fireplace in the lobby are also provided.
Pool
Hot Tub
Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
Get rates
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.

Popular places to visit

One of the best sunsets you'll find on the East Coast is here at Martha's Vineyard on Menemsha Bight. The shops in town are quaint, the seafood is out of this world and the memories will be everlasting. #EndlessSummer

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.

Menemsha Beach

Lucy Vincent Beach

If a restful vacation is part of your travel plans, Lucy Vincent Beach might be the perfect place to seek out during your trip to Chilmark. Take in the festivals and sunsets in the area.

Lucy Vincent Beach

Squibnocket Beach

Why not spend a lazy afternoon at Squibnocket Beach during your trip to Chilmark? Stroll along the beaches or experience the area's festivals.

Squibnocket Beach

Frequently asked questions

How much are vacation packages to Chilmark?
You can find an excellent flight and hotel bundle for as little as $698. 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

Chilmark Shellfish Department on Martha’s Vineyard
Chilmark Shellfish Department on Martha’s Vineyard
Chilmark, MA / United States - May 28, 2016: Landscape sunset image of Martha's Vineyard's Lucy Vincent Beach.
One of the best sunsets you'll find on the East Coast is here at Martha's Vineyard on Menemsha Bight. The shops in town are quaint, the seafood is out of this world and the memories will be everlasting. #EndlessSummer
In the fishing village of Menemsha in Marthas Vineyard. Delicious lobster rolls, clam chowder, lobster bisque etc. they'll boil your fresh lobster for you if you don't want to do it yourself. Some benches outside if you want to 'eat in' but best bet is to take your food down to the beach for a picnic.