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Search Condo Rentals in Chilmark

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Compare 57 Condo Rentals in Chilmark with updated reviews, rates, and availability.

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (188)
"I liked the location. It was older and more dated than I realized but very comfortable and perfect location. "
Southcape Resort Mashpee a Ramada by Wyndham

Dog-friendly, two-story condo with community pool - close to Mashpee Town Beach

9.8 out of 10, Exceptional, (10)
"Great well equipped condo with all you need. We stayed for one week and wished we could have stayed longer. Very close to the town beach. Good for a large family or just a couple. We would comeback again. "
Dog-friendly, two-story condo with community pool - close to Mashpee Town Beach

Coastal condo with pool, tennis courts & home comforts - close to beach

9.4 out of 10, Exceptional, (22)
"Perfect for our trip to the Beach Road weekend music festival. The restaraunt and Bar at the location is a great casual place. Pool was small but nice. Would go again."
Coastal condo with pool, tennis courts & home comforts - close to beach

Heart of downtown, walk to harbor, Martha’s Vineyard ferry, bikeway and beach!

9.6 out of 10, Exceptional, (13)
"Fantastic location, easy walking distance to shops and restaurants, but still very quiet location. Owner dining and site recommendations were spot on. We took in quite a few and were not disappointed!"
Heart of downtown, walk to harbor, Martha’s Vineyard ferry, bikeway and beach!

Large Cottage for Perfect Family Vacation

9.8 out of 10, Exceptional, (37)
"This cottage is located in a seaside vacation village. We were there off season when very few people were around. Therefore, both parking and walking around were easy. Be mindful that during this time of year some stores and restaurants are either closed or are open with reduced hours. The village was very quiet and peaceful. We had one question during our stay, which was responded to quickly. Our visit to this village was very pleasant. "
Large Cottage for Perfect Family Vacation

Dog-friendly condo with pool - explore the parks & hit the beach

9.4 out of 10, Exceptional, (53)
"Awesome location, easy check-in, good amenities in the unit as advertised. Great water pressure in shower, comfortable bed. Will stay again."
Dog-friendly condo with pool - explore the parks & hit the beach

Charming condo near ferry with roof top deck, AC, W/D, & central location

2.0 star property
10.0 out of 10, Exceptional, (3)
Charming condo near ferry with roof top deck, AC, W/D, & central location

Dog-friendly first-floor seaside cottage with pool & tennis courts

9.4 out of 10, Exceptional, (43)
"We come out to the island to enjoy short, stays every summer and it tends to be a whirlwind of a long weekend. Island Inn is the perfect spot to stay for our family. The accommodations are clean and comfortable, the property is well maintained and everyone has always been very friendly and welcoming. We bring our dogs with us (Labs) and having a large outside space that allows us to exercise them without bugging anyone who may not be dog people is priceless! I can throw the ball and walk them...
Dog-friendly first-floor seaside cottage with pool & tennis courts

Lovely studio above garage

Lovely studio above garage

Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!

10.0 out of 10, Exceptional, (64)
"The location was easy to find, instructions were clear, and the place was clean. Good stay."
Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!

The Pool Villas @ New Seabury-2 Bedroom, 2 full baths, private heated pool

9.6 out of 10, Exceptional, (30)
"Had a wonderful stay, unit had everything we needed, clean and easy to access. Sunsets were spectacular just a short drive away. Only wish we could've enjoyed the pool."
The Pool Villas @ New Seabury-2 Bedroom, 2 full baths, private heated pool

Charming suite with pool & tennis courts - 1/2 mile to the beach

9.4 out of 10, Exceptional, (18)
"It was our first time staying at Island Inn. We thoroughly enjoyed our stay. It was peaceful and it didn’t take long to get to various destinations. We’ll visit again!"
Charming suite with pool & tennis courts - 1/2 mile to the beach

Renovated Cottage Steps from Private Beach. Aug 18-24 Discounted Rate

8.6 out of 10, Excellent, (39)
"We loved our stay at the Cape location perfect! Our 2nd year renting, was a disappointment!year"
Renovated Cottage Steps from Private Beach. Aug 18-24 Discounted Rate

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

10.0 out of 10, Exceptional, (26)
"Great location"
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

Coastal getaway 1/2 mile from beach with pool & tennis courts - dog-friendly

8.8 out of 10, Excellent, (21)
"Very clean inside, convenient location. Only issues were A/C unit didn’t reach back bedroom. Horrible water pressure and backed up bathtub. Paper thin walls."
Coastal getaway 1/2 mile from beach with pool & tennis courts - dog-friendly

Cute condo with pool & tennis - close to golf & the beach

8.8 out of 10, Excellent, (43)
"Over run with ants, in the bathroom and on my toothbrush and in the kitchen had to put food in the refrig and microwave as we had to throw things out before we realized how bad the ants were. Needed better instructions for the roku tv which we got from Megan at the checkin."
Cute condo with pool & tennis - close to golf & the beach

Dog-friendly condo suite with pool, tennis & picnic area - close to beach

9.0 out of 10, Wonderful, (31)
"Took a quick trip over to MV for change of scenery from our house on the Cape. Brought the dog so our options for a rental were limited. This was perfect for what it was. Nomans is one of our favorite spots on MV, grounds were well kept. Layout of the unit was efficient and was very clean. Very friendly staff once we arrived. We rented a jeep so we had easy access to OB and Edgartown. Kids enjoyed dips in the pool. Will likely come back due to convenience ! "
Dog-friendly condo suite with pool, tennis & picnic area - close to beach

Cozy seaside escape with on-site tennis, pool & prime location

9.2 out of 10, Wonderful, (31)
"Perfectly located near the center of Oaks Bluff. Property has lots of land and a pool."
Cozy seaside escape with on-site tennis, pool & prime location

Comfortable & convenient Martha's Vineyard condo with pool - close to beach

9.0 out of 10, Wonderful, (29)
"This was a great convenient location is directly on the MVTA bus route so very easy to get around the island if traveling with no car. The grounds are set back from the main road so no noticeable street noise. Also walkable to Oak Bluffs and larger beaches if you don’t mind a 20-30 minute walk. Very clean and efficient layout to the unit, staff were helpful. Extra towels and linens were provided. There is a nice restaurant/bar next door for a quick bite or a drink and some music. Only real...
Comfortable & convenient Martha's Vineyard condo with pool - close to beach

Upscale cottage in the heart of South Cape Cod, walk to beach & marketplace

9.4 out of 10, Exceptional, (18)
"Loved this house and the location especially for a September wedding which was on the beach just a walk away. The house was very clean and just as described, I would definitely recommend this property!"
Upscale cottage in the heart of South Cape Cod, walk to beach & marketplace
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.
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Other property types in Chilmark

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

8.6 out of 10, Excellent, (22)
"We didn't realize how beautiful and unique the architecture of this residence was before we arrived. It is a gorgeous place and we were please by the cleanliness and simplicity of it. "
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

Beautiful dog-friendly home with water view, balcony & washer/dryer

7.8 out of 10, Good, (14)
"A Vacasa managed property that has everything you could want. We stayed 4 nights with our whole family and our small dog. It had everything we could want and we enjoyed ourselves. Recently redone, with good fit and finish and places to hang cook and relax off a dirt road that is well situated. Our only comments would be that there were some things needing fixing like the grill handle, lights not in sockets, and general disarray of bedding and supplies in the closets. While clean and fresh...
Beautiful dog-friendly home with water view, balcony & washer/dryer

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.

10.0 out of 10, Exceptional, (44)
"We were in town for a wedding in Chilmark and the property was exactly what we needed!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
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.

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