
Holiday rentals with beach access in Chilmark
Find and book unique rentals with beach access on Airbnb
Top-rated rentals with beach access in Chilmark
Guests agree: these rentals with beach access are highly rated for location, cleanliness and more.

101 Steps to Beach/Island/Bike Path
Experience the Seaside Town of Mattapoisett. Location! Relax in this cozy cottage that is 101 steps from the front door to the Beach/Island/Bike Path. Enjoy this popular, sought after scenic Path for walking, biking, or a day at the Beach. The path is known for its picturesque coastal views. Walking distance to the Quaint Town, Shipyard Park, and many restaurants. Ned's Point Lighthouse- 5min. Day trip to the Vineyard? Ferry- 14 min. Season Open! Early Bird Deal- 20% off wk. 3,4,5 days 10% off

Koselig Cabin on the Farm Coast of New England!
This cabin is full of comforts, convenience, and love. Just miles from Horseneck Beach. It is located under a mile to Buzzards Bay Brewery and Westport Rivers Winery and a 5 minute walk to the quiet little neighborhoods private beach on the East Branch of the Westport River. Koselig embodies feelings of family, friends, warmth, love, coziness, contentment, and comfort. We have a custom area and house guide at the Cabin with everything you need to know to maximize your experience in the area!

Loft Guest Suite in Modern Barn House
A beautiful guest suite on Martha’s Vineyard with a private entrance on the 2nd floor of the back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this large 400 square foot suite has vaulted wood ceilings and skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is centrally located, just off historic Music St, a short walk to a small town center which provides amenities. Ask about our other guest suite if you are with others.

Spectacular beach & pool combo; beautiful sunsets!
Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Sunny Studio Apartment on Martha's Vineyard
Our Sunny Studio is centrally located on Martha's Vineyard. A down-island location with an up-island feel. Open and airy studio with kitchenette and bath. The apartment has all the essentials. The apartment is located within walking distance of hiking and biking trails. A 10 to 15 minute car ride to any down-island town / beach. ***Please Note: Although conveniently located we are not within walking distance to Bars or Restaurants. We do recommend first time visitors rent or bring a car.

4-Season Guest House on Historic Chilmark Estate
Beautiful private guest house in Chilmark on Martha's Vineyard. Secluded yet convenient. Drive on pass to spectacular Chilmark beaches! Newly renovated and gorgeous. Great location - 10 minute walk to Chilmark Store. Full kitchen, living area, kitchen island/dining table, queen bed, day bed (not for sleeping), fireplace/heater, private outdoor shower, deck and picnic table, full bath inside. Keurig machine. 2 friendly labs/2 chickens on premises. Easy bus access. Old-style MV charm.

impeccable cottage STEPS to downtown OB & beach!
Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

Waterview, Private, Walk to Beach, Mile to Town
Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing. Ask the host about ferry reservations if they appear to be sold out!

Beach Glass Cottage - Pond Front
Come stay at the Beach Glass Cottage! A pristine pond front, completely renovated and tastefully decorated, 3 bedroom, 2 bathroom cottage in the heart of Hyannis. Truly the perfect get-a-way for family and friends. The Beach Glass Cottage is tucked away from the action, but within walking distance to Main Street Hyannis, which features eclectic shops, restaurants, bars, ice cream with mini golf and the Cape Cod Melody Tent is a short walk from the cottage as well.

Private Pond-side Cape Cod Home
Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.

Stylish Getaway|Outdoor Shower|Patio|walk to town
* Private garden patio: table & chairs, propane grill, propane fire pit & enclosed outdoor shower * 10 min walk to Edgartown's dining & boutiques * Cable TV, Streaming services, Sonos * High-speed WiFi, comfortable workspace in the bedroom * USB charging ports in the BR & LR * Small but mighty fully stocked kitchen for home-cooked meals * Organic, local bath products * Board games & a small library * HW floors, SS Bosch appliances, DW, W/D, HVAC

The Ideal Spot
The perfect getaway in Falmouth for all seasons! Our home is beautifully located overlooking Bourne’s Farm and we are steps away to the picturesque Shining Sea Bike Path. Enjoy a beautiful scenic 8.5 mile ride winding your way thru the Sippewisset marsh and along the coastline to the seaside village of Woods Hole. Where you can enjoy the local restaurants ,shops and science learning or jump on the ferry to Marta’s Vineyard.
Popular amenities for rentals with beach access in Chilmark
Apartment rentals with beach access

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

WATERFRONT PENTHOUSE OAK BLUFFS

Perfect Location for a Walking Vacation

Spacious & bright, near beaches

Brand new! Whole apartment, huge tub, full kitchen

Quiet & Serene in Aquinnah

Anchor Suite | Nantucket Boat | Hyannis + Parking

Main Street on the Park
House rentals with beach access

Martha's Vineyard Cottage: Walk to Town and Beach

Mid-Century Modern home 5 minute walk to beach

3BR Home, Fenced Yard, Free use of car, Pets ok!

Secluded and Serene Getaway

Entire home newly renovated in August 2025

Secluded Aquinnah Cottage

Katama Barn

Beautiful 3 bedroom in Oak Bluffs, walk to beach
Apartment rentals with beach access

Seaview Cottage

FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach

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

Serenity on Martha's Vineyard

Sunny 2bedroom condo w pool, walk to town

Cape Esacpe at New Seabury

Beachfront Complex in Hyannis

Short walk to the Beach and Downtown Hyannis!
When is the best time to visit Chilmark?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $527 SGD | $558 SGD | $515 SGD | $540 SGD | $554 SGD | $612 SGD | $755 SGD | $854 SGD | $585 SGD | $582 SGD | $609 SGD | $637 SGD |
| Avg. temp | -2°C | -1°C | 3°C | 8°C | 13°C | 18°C | 21°C | 21°C | 17°C | 11°C | 6°C | 1°C |
Quick stats about holiday rentals with beach access in Chilmark

Total holiday rentals
Explore 110 holiday rentals in Chilmark

Nightly prices starting at
Chilmark holiday rentals start at $129 SGD per night before taxes and fees

Verified guest reviews
Over 2,600 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
100 of Chilmark holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chilmark rentals

4.9 Average rating
Chilmark stays are highly rated by guests – averaging 4.9 out of 5!
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- Cape Cod
- Brown University
- Mayflower Beach
- West Dennis Beach
- Charlestown Beach
- Craigville Beach
- East Sandwich Beach
- Duxbury Beach
- Easton Beach
- Onset Beach
- Roger Williams Park Zoo
- East Matunuck State Beach
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- Second Beach
- The Breakers
- Sandy Neck Beach
- Pinehills Golf Club
- New Silver Beach
- South Shore Beach
- Nickerson State Park
- Popponesset Peninsula
- Lighthouse Beach
- Cape Cod Inflatable Park
- Point Judith Lighthouse




