Holiday rentals with beach access in Chilmark

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Popular amenities for rentals with beach access in Chilmark

Apartment rentals with beach access

Guest favourite
Flat in Middletown
4.98 out of 5 average rating, 252 reviews

Private Beach Retreat close to Newport

TylerRating, 5 stars4 weeks ago
Great host, extremely responsive and consistently checking in on us to make sure everything was spot on. The listing was accurate and everything was already taken care of before we arrived but I can imagine she would have been extremely responsive if required. I would highly recommend this place due to the proximity to downtown Newport without all of the immediate hustle and bustle and a nice cozy place to relax to end your day.
Top guest favourite
Flat in East Falmouth
4.95 out of 5 average rating, 314 reviews

In-law apt. with all the amenities of Home.

KateRating, 5 stars7 months ago
We had a short but pleasant stay at Gail’s and the in-law apartment was perfect! Check in was easy and the apartment was clean, comfortable, and well-appointed with great snacks! This is a great location for exploring Falmouth and the rest of the Cape and Gail is super friendly and responsive. We hope to stay longer next time!
Superhost
Flat in Oak Bluffs
4.88 out of 5 average rating, 153 reviews

WATERFRONT PENTHOUSE OAK BLUFFS

JustynRating, 5 stars9 months ago
We spent our anniversary at Leslie’s place and it was a beautiful! The views and location was like no other and we would book again! Leslie was very responsive and even left us some dinner when we came in late from the ferry. The restaurant staff were friendly and it was everything described in the listing. We didn’t want to leave!
Top guest favourite
Flat in Middletown
4.98 out of 5 average rating, 185 reviews

Modern beach studio 7 min walk from the beach

AngelikaRating, 5 stars1 week ago
Absolutely loved our stay here! Location is amazing and apartment is in pristine condition. Alice was an amazing host and we had great communication throughout our stay. The Airbnb also had everything needed to make sure we were comfy. Alice truly thought about everything to make sure guests feel right at home. Would recommend and will stay again!
Guest favourite
Flat in Wareham
4.91 out of 5 average rating, 177 reviews

☀️ Spacious and Bright -- The Sailboat Suite

JocelynRating, 5 stars2 days ago
We had such an amazing stay. We felt right at home and were very comfortable with the place. Carolyn was very responsive and helped with everything we needed. Shout out Ali for fixing our little problem. We loved it here and would stay again!
Top guest favourite
Flat in Tisbury
4.93 out of 5 average rating, 125 reviews

Harbor view apartment, a quick walk from the ferry

KatherineRating, 5 stars2 weeks ago
Mark's place was exactly how it appeared in photos. Great, walkable location. Easy to get to restaurants on Main St. There's a place to rent bikes just across the street. The stay was comfortable, quiet, and exceeded expectations. Thank you again, Mark!
Guest favourite
Flat in Somerset
4.91 out of 5 average rating, 154 reviews

The Crows Nest - 1747 Isaac Pierce House 2nd Floor

DorisRating, 5 stars1 week ago
The apartment is very comfortable. The pictures are accurate. Beds comfortable. Plenty of very nice bath linens. I loved the types and amount of lighting in every room. Wonderful water pressure in the shower. The kitchen is very functional . I loved cooking on the beautiful big stove. We really appreciated having both a Keurig and a coffee maker. The one thing I would caution about is the stairs. They are as pictured. We had no problem with them, but people with knee issues might. I will certainly look for this property again when in the area.
Top guest favourite
Flat in New Bedford
4.99 out of 5 average rating, 124 reviews

One Bedroom in-law near beach with breakfast

ThereseRating, 5 stars3 days ago
Monica & TJ’s listing is exactly as pictured and described. It is spotless and well appointed. The extra little touches such as quality shampoo, conditioner, shower gel (not Wally World brand), snacks, and of course the pastries upon check in- are so nice. These things tell me that they care about their guests and their experience. Great binder on the “How to use” + suggestions of things to do, restaurants, etc. Very helpful! The best part was how close to the beach this rental is! 100% would stay here again; experience to value ratio = A+ !

House rentals with beach access

Guest favourite
Home in Edgartown
4.91 out of 5 average rating, 54 reviews

Updated Beautiful Cottage in Edgartown AC

RayRating, 5 stars7 months ago
Kenneth Is a great host communicates very well and has a genuine concern for his guests Ray
Guest favourite
Home in Middletown
4.93 out of 5 average rating, 166 reviews

Renovated 2 Bed Private Vacation Home near Newport

GeRating, 5 stars2 weeks ago
Great place! Very spacious and clean. Matthew was also very accommodating and provided us with very helpful instructions about how to get in, where things are, and wifi log-in info. The backyard and frontyard were also great for our dog to explore around. We really enjoyed our stay and would definitely come back another time.
Guest favourite
Home in Mattapoisett
4.9 out of 5 average rating, 10 reviews

Buzzard Bay Getaway

AnnaRating, 5 stars8 months ago
While the weather did not cooperate (it rained the entire time) the cottage and views made up for the weather. From the table to the couch the views are wonderful. The cottage is very well stocked from towels and blankets to the kitchen. We did not need anything that wasn't supplied. The bathroom is small but functional. The shower might not work well for a larger person. The neighborhood is quiet and feels very safe and peaceful. We enjoyed our long weekend and would book this cottage again.
Guest favourite
Home in West Tisbury
4.87 out of 5 average rating, 30 reviews

Greenehill~ Up-island 1800's Vineyard farmhouse.

ShahRating, 5 stars9 months ago
We stayed over the long weekend at this beautiful property. It’s located centrally close to all the major attractions and beaches. The property had beautiful features and felt very comfortable. The home itself had a lot of charm and had a positive energy. Hosts were very kind and nice to communicate with. They left us wonderful treats and fresh eggs from their beautiful garden. Overall it was a great stay at their property. Highly recommended and we will be staying there again. I will highly recommend getting a car to travel in the island so you can go to Edgartown or other places.
Guest favourite
Home in Fairhaven
4.92 out of 5 average rating, 104 reviews

Cottage by the Sea

DonnaRating, 5 stars1 week ago
We enjoyed our weekend get away at Kara's. The bed was comfy, house had all the amenities we needed. We enjoyed sitting outside, listening to the birds and watching the bunny rabbits in the yard.
Top guest favourite
Home in Oak Bluffs
4.93 out of 5 average rating, 198 reviews

Spectacular beach & pool combo; beautiful sunsets!

AshleyRating, 5 stars1 week ago
Came here for a girls weekend. I think it’s even better than the photos! We had a great time!!!
Top guest favourite
Home in New Bedford
5 out of 5 average rating, 27 reviews

Sea-Side Shanty

KelseyRating, 5 stars1 week ago
Truly the best Airbnb experience I have had. Hosts are kind and thoughtful. They made sure we had everything we needed. House is spotless. Beds very comfortable. Perfect location with the beautiful water view. Great restaurants around. And easy trip to Boston from the local train station just 10 mins away! We hope to come back soon!!!
Guest favourite
Home in Edgartown
4.92 out of 5 average rating, 151 reviews

✅Beach ✅Downtown ✅Restaurants/Bars ✅Bike Path

DanielRating, 5 stars2 weeks ago
Great location just over 2 miles (3.5 K) from the heart of Edgartown. There is a little bit of road noise per the other reviewers but it minimal, especially at night. The place is very clean and has everything you need for a comfortable stay. We were 4 adults, stayed for 2 nights, and had a vehicle so were able to easily explore the island from this location. Other than breakfast, we ate out (lots of great places to eat on MV) but the kitchen is fully equipped should you choose to eat in. The nearby Stop and Shop grocery store is well stocked.

Apartment rentals with beach access

Guest favourite
Apartment in Vineyard Haven
5 out of 5 average rating, 21 reviews

Relax....You're on Island Time......

JocelynRating, 5 stars9 months ago
Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.
Guest favourite
Apartment in Tisbury
4.9 out of 5 average rating, 73 reviews

Sunny 2bedroom condo w pool, walk to town

ShayRating, 5 stars7 months ago
We had a great time at Leah’s place. She is a terrific communicator, immediate responses. She also reached out to share about local fun events that were happening during our stay. So nice! We would definitely stay there again.
Guest favourite
Apartment in Oak Bluffs
4.96 out of 5 average rating, 27 reviews

LOCATION LOCATION!! Ocean- View TOP Floor Condo

TaylorRating, 5 stars8 months ago
Heather's place is beautiful! An amazing location with close proximity to the OB steamship authority station, a number of bus lines, and the beach! The view and location are unbeatable! Heather was also super responsive in terms of coordinating flexible check-in/check-out times which was very much appreciated. Overall, would definitely recommend to anyone visiting OB :)
Guest favourite
Apartment in Falmouth
4.72 out of 5 average rating, 18 reviews

Condo in Falmouth MA

MarkRating, 5 stars1 month ago
The Condo was clean & comfortable. Having two bedrooms with queen beds was perfect for us, and sharing the 1 bathroom worked fine. The price was better than most other options. It was peaceful, and very quiet during our stay (in early May). Having the pool available would be very nice in summer months.
Top guest favourite
Apartment in New Seabury
4.94 out of 5 average rating, 72 reviews

Beach Cottage 3nts/4th Free in August,Mashpee MA

GeorgeRating, 5 stars9 months ago
Our second visit. We love the place. Quiet but close to great beaches and the Popponesset Marketplace is 2 minutes walk away, with fish restaurants and small stores with necessities (including wine and beer!). A highlight of this visit was sitting on the patio in the morning and 3 times seeing an osprey dive to the pond and catch a fish.
Guest favourite
Apartment in Sandwich
4.97 out of 5 average rating, 38 reviews

Sandy Neck Provisions - Full Apartment

KevinRating, 5 stars7 months ago
The location was quiet during our low season stay and close to a beach with 5 mins drive. The house was clean and had lots of board games to have fun with. Meghan was responsive to answer our questions and to addressed issues. I would stay there again in the future.
Superhost
Apartment in Hyannis
4.79 out of 5 average rating, 14 reviews

Charming Hyannis 3 Bed 2 Bath

KiaraRating, 5 stars8 months ago
Had to call maintenance for a couple of reasons but responded quickly.
Guest favourite
Apartment in Hyannis Port
4.85 out of 5 average rating, 85 reviews

Short walk to the Beach and Downtown Hyannis!

MathieuRating, 5 stars2 weeks ago
Great stay. I would definitely recommend this place. Great location for a stay in Cape Cod.

Quick stats about holiday rentals with beach access in Chilmark

  • Total rentals

    100 properties

  • Nightly prices starting at

    ₹7,715 before taxes and fees

  • Total number of reviews

    2.4K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

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