Holiday Rentals in Chilmark
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Unlock member prices with Mates Rates
You could save 10% or more on over 100,000 hotels right now.
Check rental availability in Chilmark
Holiday Rentals in Chilmark

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

Water-view home in great location with spacious backyard, grill, kayaks, dogs OK

Cozy efficiency apartment/heated pool

The Club at New Seabury

Sea Mist Resort

InnSeason Resorts Captain's Quarters

Beachside Village Resort

Charming Seaside Cottage Central to the Beach and New Seabury Resort Community

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Charming 3-bedroom house with a pool, AC, WiFi in pleasant East Falmouth

Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C

Walk to Beach & Lighthouse: Oak Bluffs Studio!

Maushop Property - First Time Available

Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

Coastal chic meets French Provençal in this newly renovated oceanfront home.

Your Oasis Awaits
Other types of properties in Chilmark you may be interested in

Water-view home in great location with spacious backyard, grill, kayaks, dogs OK
Holiday Accommodation Chilmark
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Chilmark are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Chilmark itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Chilmark holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Chilmark, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Chilmark with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.