Holiday rentals in Chilmark

My family & I have been vacationing at Larry’s Historic Arcade for the past 7+ years. It is in the most perfect spot located right on Circuit Ave in the heart of Oak Bluffs. There are many stores and restaurants located on this road and it’s super convenient to have a market right across the street for any last minute essentials. We always rent the third floor apartment. It is very spacious and has a full size bed, a loft with 2 twin size beds and a pull out couch. It also has 2 decks. One over looking circuit ave and one on the other side with a grill. The house has WiFi, 2 mini splits (for ac or heat) a tv and a full kitchen. I highly recommend booking Larry’s Historic Arcade. It has everything you need and more. Thank you Larry for providing the perfect vacation spot for me and my family. We are already looking forward to next year!

We had a really nice time and was perfect for what we needed. Short walk to the beach was nice with two gong kids. The living space was extremely clean and felt like home. Would highly recommend.

This was our first stay at an air bnb. Now the bar is set high. After the second day we caught ourselves saying “let’s get home “ . The neighborhood is friendly and quiet. We were so happy that your place was our first.

The Swiss House is an ideal retreat for families seeking a harmonious blend of comfort and connection. The expansive open-concept living area downstairs fostered a sense of togetherness, while the well-appointed kitchen made preparing family meals a breeze. Nestled away from the hustle, yet conveniently close to amenities, the house offers a perfect balance of privacy and accessibility. A quick drive to Mayflower Beach added to the allure, making our stay nothing short of delightful.

Brian was a great host. The place was immaculate and well located. Would definitely stay here again no questions asked. 10/10

quaint little cottage!!!! easy access to restaurants.. shopping... groceries.... responsive host with excellent communication!!! Great books and information about the area.. and surrounding areas!!!!

My friends and I stay at Maureen’s cottage every February for a winter stitching getaway. The house is perfect for the 3 of us. It has 3 comfortable bedrooms and 2 full baths. The living room is spacious. We love the kitchen and dining table. We set up our stitching gear and stitch the days away until it’s time to say goodbye. There are so many great restaurant choices close by. We highly recommend the Keltic Kitchen a short distance away on rte 28. Perfect breakfast place. We also tried for the first time a very small Thai restaurant, Bangkok Kitchen. The food was delicious and very nice people. Back to Maureen’s Beach Glass Cottage…just a perfect place to stay. The amenity list does not even begin to cover what they have available. It’s the perfect getaway home in my opinion. The one floor living is great for us with 1 of us having mobility issues. We cannot wait to come back. Thank You!

Kenneth Is a great host communicates very well and has a genuine concern for his guests Ray

We absolutely loved Nicole’s place. It’s in a quiet neighborhood and very easy to get to. We used it as a starting point on some trips to Plymouth and Newport. The house is set up very well, had all the amenities we needed, and was very comfortable. Our kids loved going to the beach every day, which is only a two minute drive away, and easily walkable. Nicole also shared several recommendations with us and she did not disappoint! I’d highly recommend her cottage.