Photo by Wen C.

Search Vacation Homes in Chilmark

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 663 Vacation Homes in Chilmark with updated reviews, rates, and availability.

Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths
9.8 out of 10, Exceptional, (9)
"Lovely, comfy cottage with a great view. Clean and nicely decorated. Would appreciate better towels and softer pillows. Some games on site."
Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
6.0 out of 10, (19)
"There were times when the shower in the master bathroom only emitted cold water. The water spigot in the tubs would not turn completely off in bathroom in the hallway. I had trouble with the lockbox. Maybe add more specific directions. It would have been helpful to know that MV transit bus was available at the intersection of the street and County Road."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Maushop Property - First Time Available
10.0 out of 10, Exceptional, (23)
"Perfect place, just as advertised. Clean and quaint with all the conveniences. Great size for someone traveling alone or a couple. Would come back."
Maushop Property - First Time Available
Save an average of 15% on thousands of hotels when you're signed in
Cozy yellow cottage with nearby beach access.
Cozy yellow cottage with nearby beach access.
Adorable waterfront home w/ boat access & a three-season sunroom
9.2 out of 10, Wonderful, (15)
"On the whole, we enjoyed our stay. Had informed Vacasa that we wouldn’t arrive in Falmouth until midnight 4/25 (as we picked up relatives at Logan Airport), but it hadn’t been forwarded: the sloping entry to the cottage was pitch-dark! In the morning we found garbage cans tipped over, & trash strewn all around the yard —the same thing happening the second night (both times we had to clean up a mess). We requested an hour’s leeway for departing 4/27, which was to have been relayed to local owner;...
Adorable waterfront home w/ boat access & a three-season sunroom
Your Oasis Awaits
10.0 out of 10, Exceptional, (27)
"Great area for family"
Your Oasis Awaits
Cozy Massachusetts Escape w/ Patio, Near Beaches!
Cozy Massachusetts Escape w/ Patio, Near Beaches!
3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights
9.6 out of 10, Exceptional, (19)
"The house is in the middle of everything Falmouth. We had a nice stay!"
3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights
Boating, Beach, Sunsets and fun for all
9.8 out of 10, Exceptional, (18)
"We really enjoyed our week at this property. Beautiful views and neighborhood. Very clean and everything we ever could have needed was supplied. Highly recommend."
Boating, Beach, Sunsets and fun for all
Private cottage nestled in center of island, access to Lambert's Cove beach
10.0 out of 10, Exceptional, (27)
"Host was exceptional. Very quiet and secluded. Central on the island for all points of interest. The cottage was private and well appointed."
Private cottage nestled in center of island, access to Lambert's Cove beach
Maushop - 6 Hammock Pond Rd
9.4 out of 10, Exceptional, (20)
"Wonderful location to the beach and excellent stay. Washer and dryer repairmen were supposed to come out but never showed up but that's not the owner's fault though. Twin beds downstairs were very creaky everytime you turned. May I suggest a step stool in the kitchen because some of the cupboard shelves were very high. All in all,it was a very nice place to stay in."
Maushop - 6 Hammock Pond Rd
SPECTACULAR SUMMER RETREAT
9.8 out of 10, Exceptional, (9)
"Nice location, well maintained and clean."
SPECTACULAR SUMMER RETREAT
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
10.0 out of 10, Exceptional, (2)
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
9.0 out of 10, Wonderful, (37)
"Very clean and updated property! Conveniently located near the water. Comfortable place for us to rest and give my daughter/husband their space. Recommend this place and look forward to hopefully staying again. My only suggestion is to add dimmable lighting. We felt on stage in the living/kitchen area, bedroom. It would be nice to turn down bathroom light during the night."
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
10.0 out of 10, Exceptional, (158)
"We had a great vacation dispite the weather. The property could not have been nicer!"
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
8.2 out of 10, Very Good, (24)
"Upon entering the property, everything was very clean and welcoming. The rooms were spacious and comfortable. It felt like home. We would definitely book this property again."
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Stunning East Falmouth Home w/ Pool and Central AC RPAM038
10.0 out of 10, Exceptional, (7)
"Spacious, clean, loved the pool"
Stunning East Falmouth Home w/ Pool and Central AC RPAM038
First Time Available to Rent in 40 Years
9.4 out of 10, Exceptional, (25)
"Coupd hv been better, nothing to do with house just a string of duster events"
First Time Available to Rent in 40 Years
Walk your way into Vineyard Haven from Walker Way!
10.0 out of 10, Exceptional, (33)
"The owner was very nice and friendly and the property was well kept. I would definitely rent again"
Walk your way into Vineyard Haven from Walker Way!
New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖
10.0 out of 10, Exceptional, (2)
"Our stay at 36 Garrison could not have been better! The property is brand new, all the comforts of home and all the extras of a luxury hotel! The perfect combination!! Thank you."
New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖
Don't see what you're looking for?
See all available properties in Chilmark
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.

Other property types in Chilmark

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
8.4 out of 10, Very Good, (18)
"Overall my friends and I have come twice to the Noyes house and are planning to come back next year. As long as you’re comfortable not staying near the main towns, it’s an ideal location - close to the markets and stores of west tisbury, several of the best beaches on the island (Lucy Vincent and Aquinnah in particular), the Chilmark general store, and some of the best farms like beetlebung. The house is something between rustic and luxury, which is deal for a group of friends. It’s not a big...
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
10.0 out of 10, Exceptional, (36)
"Enjoyed the property completely. Loved the fact that we could walk to The dock and get fresh seafood and prepare it and dine on the deck with incredible views!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Beautiful dog-friendly home with water view, balcony & washer/dryer
9.4 out of 10, Exceptional, (8)
"Overall, the house was great — very clean, lots of space, beautiful property. My 3 star review has to do with a couple of issues and a lack of responsiveness from the owner/property manager. When we arrived, the code to open the lockbox didn’t work. I texted the owner (maybe a bot rather than a live person?) who could not solve the problem. I was told “our local team is working on the issue.” We wondered around the house and eventually found an open door. The “local team” never came or got in...
Beautiful dog-friendly home with water view, balcony & washer/dryer
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.

Recent reviews of Chilmark hotels
Expedia verified reviews