Holiday rentals with beach access in Chilmark

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Popular amenities for Chilmark Accommodation with Beach Access

Apartment rentals with beach access

Top Guest favourite
Apartment 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
Apartment 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
Apartment 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
Apartment in Dennis
4.91 out of 5 average rating, 113 reviews

2 BD Suite Mayflower Beach & Dennis Village

KimRating, 5 stars7 months ago
Christina’s home was pretty, quiet, comfortable and well stocked. We appreciated that there was coffee, tea, sugar, soap and everything we needed in the kitchen. The location was also superb- very close to several gorgeous beaches plus multiple restaurants and shops. We did not have a chance to use them, but she even had bikes, which would be wonderful in warm weather. This is a great listing. I thoroughly recommend it!
Superhost
Apartment in Fairhaven
4.77 out of 5 average rating, 109 reviews

Main Street on the Park

VivekRating, 5 stars3 weeks ago
Beautiful and well-maintained place. We had a minor issue, but Jonas was very proactive in resolving it. Felt right at home.
Guest favourite
Apartment in Barnstable
4.95 out of 5 average rating, 122 reviews

Centerville Studio with Town Beach Pass

AndrewRating, 5 stars1 month ago
Great internet. Super clean. Would definitely stay again. Five stars.
Guest favourite
Apartment in Wareham
4.94 out of 5 average rating, 159 reviews

⭐ Gorgeous Beach Views -- The Sand Dollar Suite

GinaRating, 5 stars1 month ago
Relaxing girls get away weekend. Amazing views, very walkable and friendly town and beach. (Delicious local ice cream shop- vegan options too!). The perfect place to relax, catch up with friends, and make some delightful memories.
Top Guest favourite
Apartment in New Bedford
4.99 out of 5 average rating, 124 reviews

One Bedroom in-law near beach with breakfast

ThereseRating, 5 stars1 week 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+ !

Holiday 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
Top Guest favourite
Home in Tisbury
5 out of 5 average rating, 17 reviews

Family Friendly 5 BR, Walk to Town, Beach & Ferry!

LindsayRating, 5 stars6 days ago
What a wonderful stay we had! The house was stocked with anything you could think of and the host Caroline was readily available for any questions. Will absolutely come back and recommend to all!
Top Guest favourite
Home in Yarmouth Port
4.99 out of 5 average rating, 351 reviews

Fabulous Waterfront! 3bdrm/2bth Kayaks & Firepit

CharlotteRating, 5 stars1 week ago
Serene and charming riverfront hideaway. In a residential neighborhood but very quiet. You are 5-10 minutes from great restaurants, shopping, Dennis Beach but it all feels very secluded. We went kayaking every day from the private dock, saw swans, sea lions, and hawks. The space is clean, boho-chic, very comfortable beds, easy to use gas fireplaces. Primary bedroom sitting area/sunroom is dreamy for reading. Kitchen has everything you need. We thought we might miss an ocean/bay view but we didn't at all. Very reasonably priced for the quality. Meg replied to all messages within minutes. We would absolutely come back. Great for a couple or small family.
Top Guest favourite
Home in Woods Hole
5 out of 5 average rating, 63 reviews

Modern Marvel in Woods Hole - Walk to town & ferry

DoreenRating, 5 stars1 week ago
We traveled with 4 couples who have know each other since HS, 40 years ago. It was a great home to relax and catch up. The house is lovely and we loved that we each had our full bath! I highly recommend this home and this location.
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, 199 reviews

Spectacular beach & pool combo; beautiful sunsets!

RobynRating, 5 stars3 days ago
Resort vibes with a chef's kitchen and stunning views! ***** Our stay at Larry's house was fantastic! The kitchen was absolutely amazing - spacious, modern, and fully equipped with everything we needed. We enjoyed cooking and gathering there. The real highlight was the outdoor space. The view was breathtaking! The pool and hot tub made it feel like we were staying in a private resort. Michael was helpful and responsive, making everything easy from check in to check out. We would love to come back.
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.

Holiday condos with beach access

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

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

JocelynRating, 5 stars10 months ago
Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.
Guest favourite
Condo 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
Condo in Oak Bluffs
4.96 out of 5 average rating, 27 reviews

LOCATION LOCATION!! Ocean- View TOP Floor Condo

TaylorRating, 5 stars9 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 :)
Superhost
Condo 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
Condo 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
Condo 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
Condo 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
Condo in West Falmouth
4.97 out of 5 average rating, 29 reviews

Lovely W Falmouth Home steps to bikeway & more!

LaurenRating, 5 stars6 days ago
We had a fantastic time here! We were in Falmouth for a bachelorette weekend and this apartment was convenient and close to everything we wanted to do. The space was super cute and clean, perfect for our group! Adam was super helpful during our stay too. We definitely recommend.

Quick stats about holiday rentals with beach access in Chilmark

  • Total rentals

    100 properties

  • Nightly prices starting at

    $150 NZD 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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