Vacation Homes in Chilmark, MA
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Top Vacation Homes in Chilmark

Historic Oak Bluffs home, short walk to town, beach, and harbor.

Newly renovated 2BR house, FREE CAR w/beach sticker, pet friendly, sleeps 8

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

Oak Bluffs - Quiet neighborhood

Beachfront On John's Pond, Indoor HEATED Pool, and Dock!

The Seashell Cove - Martha's Vineyard

West Falmouth Cottage in the Heart of This Historic Village.

Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach

Breathtaking Views with Private Dock & Pool!

Cape Cod Retreat by the Beach

Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
Top hotels in Chilmark

Summercamp
Find the Best Vacation Homes in Chilmark
Why book a vacation home in Chilmark?
Vacation homes in Chilmark make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Chilmark?
Private Chilmark rental homes range between - per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Chilmark vacation home rentals. You might look for Chilmark rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Chilmark offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Chilmark?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Chilmark. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Chilmark hotels and vacation homes that best suit your stay. We also have deals for flights, and Chilmark car rentals. You’ll save even more when you bundle your items into a Chilmark vacation package!
How many vacation homes are available to book in Chilmark?
There are 934 rental homes in Chilmark. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Chilmark?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Chilmark Vacation Homes essential information
Accommodation | 934 Vacation Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | Historic Oak Bluffs home, short walk to town, beach, and harbor., Newly renovated 2BR house, FREE CAR w/beach sticker, pet friendly, sleeps 8, Located Steps Away To Main Street And .7 Miles From Surf Drive Beach, Oak Bluffs - Quiet neighborhood, Beachfront On John's Pond, Indoor HEATED Pool, and Dock! , The Seashell Cove - Martha's Vineyard, West Falmouth Cottage in the Heart of This Historic Village. , Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach, Breathtaking Views with Private Dock & Pool!, Cape Cod Retreat by the Beach, Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown, Quintessential waterfront cottage with screened porch - steps to Waquoit Bay |