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

Newly Renovated! Seconds to sand, fire pit, A/C
Recently Renovated! This Cape Cod Cottage is completely refreshed top to bottom. Less than 60 seconds to the sand. Cape cod vacations do not get any better than this! Located on idyllic Monomoscoy Island known for its gorgeous wildlife and stunning waterways, our home is the perfect choice to rent on Cape Cod. We are less than 10 Mins to Mashpee Commons and famous Mashpee Town Beach, Less than 5 mins to New Seabury and the Popponesset Inn, and only 15 mins to downtown Falmouth. Linens included!

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.

Harbor view apartment, a quick walk from the ferry
This is a great one bedroom apartment on the second floor of a house. My place is close to the beach, public transport, the Steamship Authority ferry, Black Dog Tavern, Main Street Vineyard Haven, Stop & Shop grocery, and lots of great shopping. You’ll love the convenience! Walk to the apartment right off the ferry boat. Lots to do in walking distance, and onsite parking. The Martha's Vineyard Museum is a 5 minute walk, down the same street. My place is great for couples and solo adventurers.

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!

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 Deals! September/October-15% OFF.

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

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

Sunny Private studio amazing deck kayaks & kitchen

Quiet & Serene in Aquinnah

Main Street on the Park
House rentals with beach access

The Lobster Pot: Lake Tashmoo, beachfront

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

Secluded and Serene Getaway

Newly renovated garden carriage house

Entire home newly renovated in August 2025

Beautiful 3 bedroom in Oak Bluffs, walk to beach

Antique Farmhouse w/ modern updates West Tisbury

The Blue Lagoon, Oak Bluffs
Apartment rentals with beach access

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

Private Ocean Overlook! Serene Cape Cod Escape

Cape Esacpe at New Seabury

Short walk to the Beach and Downtown Hyannis!

Lovely W Falmouth Home steps to bikeway & more!
When is the best time to visit Chilmark?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $523 SGD | $553 SGD | $511 SGD | $535 SGD | $549 SGD | $607 SGD | $749 SGD | $847 SGD | $580 SGD | $578 SGD | $604 SGD | $633 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 120 holiday rentals in Chilmark

Nightly prices starting at
Chilmark holiday rentals start at $128 SGD per night before taxes and fees

Verified guest reviews
Over 2,660 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
120 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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- Rentals with a kayak Chilmark
- Rentals with beach access Dukes County
- Rentals with beach access Massachusetts
- Rentals with beach access United States
- Cape Cod
- Brown University
- Mayflower Beach
- West Dennis Beach
- Charlestown Beach
- Craigville Beach
- East Sandwich Beach
- Duxbury Beach
- Easton Beach
- Onset Beach
- East Matunuck State Beach
- Roger Williams Park Zoo
- Bonnet Shores Beach
- Second Beach
- The Breakers
- Pinehills Golf Club
- New Silver Beach
- Sandy Neck Beach
- South Shore Beach
- Nickerson State Park
- Lighthouse Beach
- Popponesset Peninsula
- Point Judith Lighthouse
- Cape Cod Inflatable Park




