Chilmark Vacation Homes

A dock with boats, a small wooden structure, and a forested shoreline.

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Our top choices for Chilmark holiday homes

1. Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Fairhaven

Zachary S.

HK$3,706 total

includes taxes & fees

10 Aug - 11 Aug

2. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

Bethann N.

HK$4,968 total

includes taxes & fees

7 Sept - 8 Sept

3. Wooded Vineyard Retreat Near Beaches & Town

Edgartown

HK$8,608 total

includes taxes & fees

18 Aug - 19 Aug

4. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs

Karen M.

HK$12,064 total

includes taxes & fees

5 Sept - 6 Sept

5. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Oak Bluffs

Sherri R.

HK$11,093 total

includes taxes & fees

6 Sept - 7 Sept

6. Walk to Town/Golf Club - Renovated Edgartown Home

Edgartown

Steven M.

HK$8,850 total

includes taxes & fees

2 Sept - 3 Sept

7. NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Tisbury

Jennifer T.

8. New 4 BR house near center and beaches with bikes

Katama

Susan M.

HK$11,461 total

includes taxes & fees

7 Sept - 8 Sept

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Top Chilmark Hotel Reviews

Inn on the Square

10/10 Excellent

"This place isn’t fancy but everything was clean and the staff was wonderful. A perfect resting spot"

Admiralty Inn & Suites - a Red Collection Hotel

8/10 Good

"1- cleaning room but the towels stained although they change the towels every day 2- staff are friendly but they don't fill the soup dispenser 3- the breakfast is not good no variety the same scrambled egg and waffles only every day no change 4- they are very friendly but they saw that I had a lot of heavy bags eventhough they put me on the second far away from the reception with no elevators"

Mansion House Inn And Spa

10/10 Excellent

"We absolutely loved our stay at Mansion House Inn & Spa. This was our first trip to MV, and we didn't really know where we should stay, but we are so happy we ended up staying in Vineyard Haven, and specifically at Mansion House. The Inn is so beautifully decorated, the location is super convenient, and I honestly don't think I have ever stayed at a place that is so clean. Everything is pristine - including the stairwells! The beds are super comfortable, and the linens are all top notch. Everyone was so helpful, and really wanted to help us put together the best weekend. We followed all of their tips, and just had such a memorable long weekend there. We loved the low-key vibe of Vineyard Haven. It was fun to go to Oak Bluffs and Edgartown, but we really appreciated coming back to the more relaxed feel of Vineyard Haven. We greatly enjoyed the shops and the restaurants that were just steps from the hotel. We also enjoyed an amazing couples massage at the spa. We unfortunately did not make it up to the rooftop deck until the last day. The view up there is phenomenal and it would have been great to enjoy my morning coffee up there. On the last day, upon recommendation of the hotel staff, we took the free island bus to Aquinnah. The views there are absolutely spectacular. Thank you to all of the staff at Mansion Inn for helping us enjoy such a memorable time on MV!"

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