
Vacation rentals with outdoor seating in Chilmark
Find and book unique accommodations with outdoor seating on Airbnb
Top-rated accommodations with outdoor seating in Chilmark
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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!

Secluded Up Island Cottage
Charming Martha's Vineyard post and beam house on two secluded acres with two bedrooms in West Tisbury. The master bedroom has a queen bed, the second bedroom has a full bed, the loft has a full size futon. It is peacefully tucked away at the end of a road with only three other houses on it. It has easy access to beaches, bike paths and walking trails. Enjoy some family time in the wooded backyard grilling or relaxing with an outdoor shower or napping in the hammock after a day at the beach.

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.

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.

Brand new gorgeous 2 bedroom guest house.
This is a gorgeous brand new 2 bedroom guest house on the bike path that leads to downtown Edgartown and both State Beach and South Beach, as well as 1/4 of a mile from the famous Morning Glory Farm Stand. There are cathedral ceilings in the living room, which provide a open, spacious feel. There is a large deck on the front of the house with a grill, table and chairs. Part of it is covered in shade. Separate parking for guests with privacy, as it sits 200+ feet from the main house.

Vineyard Haven Walk to Ferry
I love this neighborhood! It is quiet, peaceful, and only a short walk to either Tashmoo Beach or downtown Vineyard Haven and the ferry. The house has plenty of outdoor space with it's own wood fired pizza oven, fire pit, and decks. There are nice seating areas near the fire pit, on the lower deck and on the upper deck. Walk through the backyard, down a dirt road and be at the water in five minutes. Beach towels included! Plenty of sliding glass doors and LOTS of light. Vitamix included!

East Chop Cottage - walk to lighthouse & beach!
This quaint little cottage is located in the heart of East Chop, a neighborhood of Oak Bluffs. East Chop features the high, prominent bluffs that gave Oak Bluffs its name. A lighthouse, East Chop Light, stands at the north end of the chop on Telegraph Hill- only a five minute walk from the cottage. The cottage is a twelve minute walk to the harbor, and about a mile from the Oak Bluffs ferry! There is a public beach about 1/2 mile down the road. ***This space is not suitable for children

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.

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! 10% off wk!

The Luxury Vineyard Yurt
Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

Stylish retreat | walk to town | fire pit
* 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 Chilmark outdoor seating rentals
House rentals with outdoor seating

Mid-Century Modern home 5 minute walk to beach

Juniper Point Cottage With Ocean View

Waterview, Private, Walk to Beach, Mile to Town

Beautiful 3 bedroom in Oak Bluffs, walk to beach

Top-Rated Island Retreat: Hot Tub, Lamberts Cove!

Sweet little post and beam

Antique Farmhouse w/ modern updates West Tisbury

South Coast Artists' Farmhouse
Apartment rentals with outdoor seating

WATERFRONT PENTHOUSE OAK BLUFFS

15 Acres of Open Fields & 15 Minutes to the Beach

Brand new! Whole apartment, huge tub, full kitchen

Top floor with views and steps to private beach

Walk downtown from our terrace apartment

Main Street on the Park

Cozy Large Private Pet Friendly Studio

One Bedroom in-law near beach with breakfast
Condo rentals with outdoor seating

Walk to Beach & Ferry: AC + Private Yard

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

A Perfect. Walk to beach, harbor and Main Street

Private 3bdrm Condo Tashmoo Woods

Private Ocean Overlook! Serene Cape Cod Escape

Cape Esacpe at New Seabury

2BR dog-friendly 2-story condo with community pool

Millie's-Historic New Bedford, 2BR, water views
When is the best time to visit Chilmark?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $554 CAD | $600 CAD | $611 CAD | $554 CAD | $549 CAD | $668 CAD | $799 CAD | $900 CAD | $585 CAD | $590 CAD | $554 CAD | $554 CAD |
| 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 vacation rentals with outdoor seating in Chilmark

Total vacation rentals
Explore 120 vacation rentals in Chilmark

Nightly prices starting at
Chilmark vacation rentals start at $139 CAD per night before taxes and fees

Verified guest reviews
Over 3,440 verified reviews to help you choose

Family-friendly vacation rentals
100 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
120 of Chilmark vacation 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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