"The New Seabury resort is beautiful & has excellent customer service. The 4/5 stars is because the unit we stayed in needs some updating. However, the layout, cleanliness, & location is good."
"The New Seabury resort is beautiful & has excellent customer service. The 4/5 stars is because the unit we stayed in needs some updating. However, the layout, cleanliness, & location is good."
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.
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.
We stayed for 2 nights in early Aug 2015. When we checked in we were told we had an upgrade due to a large group staying at the hotel. We ended up with a huge suite! It was very quiet, peaceful and relaxing. There is a great restaurant and bar right in the inn and also a fun pub next door that features live music, lots of fun! The bed and linens were excellent and the room size was very large. A bit of a "grand old dame", but well-maintained and very clean. Staff helped with taking the...
We stayed for 2 nights in early Aug 2015. When we checked in we were told we had an upgrade due to a large group staying at the hotel. We ended up with a huge suite! It was very quiet, peaceful and relaxing. There is a great restaurant and bar right in the inn and also a fun pub next door that features live music, lots of fun! The bed and linens were excellent and the room size was very large. A bit of a "grand old dame", but well-maintained and very clean. Staff helped with taking the...
There were chairs to bring to the beach, bath towels in the room for each person. The bed & pillows were very comfortable, AC working very well, nice clean bathroom. The included breakfast had mutliple choices and all very tasty.
There were chairs to bring to the beach, bath towels in the room for each person. The bed & pillows were very comfortable, AC working very well, nice clean bathroom. The included breakfast had mutliple choices and all very tasty.
Jamie
Reviewed September 13, 2026Reviewed September 13, 2026
My wife and I were celebrating our anniversary and decided to head to Cape Cod. With so many options of where to stay we began to read reviews and settled on the Inn on the Sound. I cannot be happier. The facilities were great, the room spacious and tastefully decorated and the food (breakfast) was outstanding. The location made walking to the beach or to dinner, only a few steps away. I would highly recommend staying here. Jon, Debbie and team should be congratulated on running a first rate...
My wife and I were celebrating our anniversary and decided to head to Cape Cod. With so many options of where to stay we began to read reviews and settled on the Inn on the Sound. I cannot be happier. The facilities were great, the room spacious and tastefully decorated and the food (breakfast) was outstanding. The location made walking to the beach or to dinner, only a few steps away. I would highly recommend staying here. Jon, Debbie and team should be congratulated on running a first rate...
Everything you need to know about Chilmark vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chilmark vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chilmark vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Chilmark vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Chilmark. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .
Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chilmark vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. The selection of Chilmark vacation rentals we have selected for you start as low as CA $180 per night. Entering your travel dates in the search wizard you might find even better deals!
How to find incredible deals on Chilmark rentals
At Expedia, we put the best Chilmark vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Chilmark rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chilmark vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chilmark. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
Frequently Asked Questions
Can I find vacation rentals in Chilmark?
Yes, there are vacation rentals in Chilmark near Chilmark Chocolates, or you can select a more secluded option if you're looking for extra privacy while you relax. Chilmark is known for its beaches and wineries. Make sure you have time to check out the festivals and local tours during your trip.
What are some of the best vacation rentals that Chilmark has to offer?
Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel: This vacation home near Chilmark is located near the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.
How many vacation rentals are there in Chilmark?
Choose from 65 Expedia vacation rentals in Chilmark for a memorable vacation.
What’s there to see and do in Chilmark?
Family-friendly attractions include Chilmark Chocolates and Fulling Mill Brook Preserve, whereas Menemsha Beach and Edys Island are a couple of great spots to enjoy the outdoors. While here, Chilmark Town Hall and Chilmark Public Library are other places worth a visit.
What’s a vacation rental in Chilmark like?
A vacation rental is a private property where you can stay for a long or short time in Chilmark. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.