Chilmark Holiday Rentals
Holiday Rentals in Chilmark
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Beautiful dog-friendly home with water view, balcony & washer/dryer
The Club at New Seabury
InnSeason Resorts Captain's Quarters
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Romantic seaside getaway with pool & tennis courts - dog-friendly
Quiet duplex by the beach, short walk to Falmouth Village, 2GBps Internet.
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Adorable waterfront home w/ boat access & a three-season sunroom
Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths
Beautiful bright home with firepit, deck & backyard - walk to beach
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
Water Front DREAM vacation, AC, skylight, Free wi-fi,free linen,with fire pit
Breathtaking Views with Private Dock & Pool!
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Other types of properties in Chilmark you may be interested in
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Sea Crest Beach Resort
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chilmark holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Chilmark. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chilmark. Seeing all the best attractions is bound to make you fall in love with Chilmark. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chilmark short-term rentals, that won’t be hard to do.
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