Holiday Rentals in Chilmark
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Holiday Rentals in Chilmark

Beachside Village Resort

Sea Mist Resort

InnSeason Resorts Captain's Quarters

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

The Club at New Seabury

Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.

Chappy Summer Cabin!

Newly Renovated Apartment in the heart of Edgartown on the Bike Path!

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

New Seabury Cape Condo + Pool & Beach Escape

Private cottage nestled in center of the Vineyard

Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

★The Islander | Steps From Water, Fire Pit, AC★

Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Other types of properties in Chilmark you may be interested in

Sea Crest Beach Resort
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.
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