Holiday rentals with a patio in Chilmark

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Top-rated rentals with patio in Chilmark

Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.

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Guest favourite

Home in New Seabury

5 out of 5 average rating, 37 reviews

Beachfront Cottage

This 2-bedroom New Seabury beachfront cottage overlooks the Nantucket Sound which offers breathtaking views & a spacious patio perfect for morning coffee, barbecues, and stargazing. It is only a few steps to the private beach and a short walk to Popponesset Marketplace, the best place to grab food & drinks while enjoying live music & mini golf - quintessential Cape Cod summer living! *Popponesset Marketplace (10min walk) is closed during the off season but Mashpee Commons(10min drive) is open*

Top guest favourite

Townhouse in Oak Bluffs

5 out of 5 average rating, 6 reviews

Oak Bluffs Renovated Retreat

Fully renovated for 2025, this 3-bed, 2.5-bath townhome invites you to unwind with a community pool, tennis courts, and direct access to Sengekontacket Pond. Inside, a custom chef’s kitchen, new baths, and luxury furnishings set an upscale coastal tone. The main level flows from a sun-lit living room to dining area / deck, and powder room. The entire second floor is reserved for the primary suite. The walk-out lower level offers two guest bedrooms, a full bath, laundry, and a private patio.

Guest favourite

Flat in West Tisbury

5 out of 5 average rating, 63 reviews

Butterfly Farm Sanctuary Bright Sunny Studio Apt

Spacious & serene in a rural setting of West Tisbury. Private, modern, light-filled studio on the first floor walkout of a newly built 2021 post and beam home. Beautifully landscaped, abutting the state forest. Full amenities, 10ft high ceilings, windows and French doors with stone patio sitting area. Studio is down a long dirt driveway located mid-Island, near beaches, trails, and 15 minute drive to all towns. Close to the Farmers Market, Artisan fair & General Store. The perfect retreat!

Top guest favourite

Home in Oak Bluffs

4.97 out of 5 average rating, 35 reviews

Pinkletink Plantation

Your family will be close to everything when you stay at this centrally-located place. Less than a mile from the heart of Oak Bluffs and Circuit Ave., where you'll find all the famous restaurants, harbor & night life. A half mile from Eastville Beach (fabulous sunsets). Take a morning stroll around "the chop"-East Chop & walk or run a 5K. Less than 2.5 miles from Farm Neck Golf Club- & 2.5 miles to State Beach. It has a well equipped kitchen, laundry, outside shower, & back yard!

Top guest favourite

Guest house in Edgartown

4.92 out of 5 average rating, 103 reviews

Martha’s Vineyard Cottage - A Glamping Experience!

This is your vineyard home, where you can walk or ride a bike less than a mile to the beach or two into town. Get the glamping experience with kitchenette, A/C, an outdoor shower, a composting toilet, a queen bed in the loft and futon couch that can sleep two more in the living room. Enjoy outdoor games, outdoor seating, a Weber grill for bbq, tv, WiFi, cozy indoor space and more, right on the bike path with a bus stop for easy accessibility or free car parking. Whatever you want!

Guest favourite

Flat in Fairhaven

4.87 out of 5 average rating, 69 reviews

Heart of Fairhaven Studio

Vibrant studio in the center of Fairhaven. Our place is a short walk to shopping and restaurants, and features: - Private entrance - Kitchenette - Remodeled backyard with turf - Minutes from ferry to Martha’s Vineyard & Nantucket - Under 10 min from the NEW train (T) to Boston With so much to explore (30min to PVD, Newport, Cape Cod), we recommend renting a car. There is limited public transportation. Notes: On-street parking & the stove is a 2-burner electric hot plate.

Guest favourite

Home in Edgartown

5 out of 5 average rating, 37 reviews

Valentine's Retreat Hot Tub Fire Pit Trails Beach

LOCATION LOCATION ✅ Rated Top 5% of Homes ✅Cleanliness, Fully stocked kitchen ✅Pet-Friendly, Minutes from ferry & beaches ✅ Peaceful & private neighborhood ✅ HotTub, Fire Pit, Trails at your door step, perfect for peaceful strolls or energetic hikes through lush landscapes. AND Flexibility, with Every detail curated for comfort and style, you'll feel at home the moment you step inside. Located with the island's natural beauty around you, unwind and reconnect with nature.

Guest favourite

Cottage in Oak Bluffs

4.96 out of 5 average rating, 151 reviews

Beautiful and walk to everything Oak Bluffs!

This is a beautiful cottage in the heart of Oak Bluffs! Walk to town, the inkwell beach and the harbor! This modern and comfortable space will be the perfect home base for you and your family. Enjoy all the amenities including central air. Coffee maker, full laundry, outdoor shower and a beautiful patio too. We are on property eager to make your stay as magical as possible. Please check the reviews of our other listings to see how guests enjoy our properties.

Guest favourite

Guest house in Tisbury

4.96 out of 5 average rating, 83 reviews

King bed, Water Views,AC,Near Bike Path- Bus stop

Have your morning coffee looking out at the sunrise and sailboats from your living room or bedroom windows. This modern studio feels secluded while only a mile and a half from Main Street Vineyard Haven, four miles from Oak Bluffs, and eight miles to Edgartown. This is the perfect place to unplug but does come equipped with everything you need, including wifi, smart tv, fully equipped kitchen, beach towels, linens, and bath towels for your stay.

Superhost

Home in West Tisbury

5 out of 5 average rating, 9 reviews

Behold the Beach - Steps from Lamberts Cove Beach

5 BR House sleeps 11 or 6 BR w/cottage for Extra charge & sleeps 4 more-Both have A/C & Heat. See property details for price to add cottage. ONLY 3 min walk to Lambert's Cove Beach. Never miss a beach day due to no parking. Relax in privacy on a peaceful 1 acre homestead in a restored 1900 farmhouse. KING beds. Wrap around deck w/ rockers & screened in porch for all day enjoyment. Lounge in a hammock. Enjoy leisurely lawn games & ping pong.

Guest favourite

Guest house in Dartmouth

4.89 out of 5 average rating, 148 reviews

Lovely Lakeside Cottage

Keep it simple at this peaceful and centrally-located cottage. Lovely lakeside cottage with open floor plan. Centrally located in southeastern Massachusetts with short drives to Boston, Providence, Newport, and Cape Cod. Several beaches within 20 minutes. Washer/ Dryer on site and California King Size bed. A simple five (5) minute ride to UMass Dartmouth. Cottage has a living room, full kitchen, bedroom, full bath, and small dining area.

Top guest favourite

Guest suite in West Falmouth

4.99 out of 5 average rating, 177 reviews

The Sea-Cret Garden, Guest Apartment

Kick back and relax in this calm, stylish space! This comfortable and peaceful guest apartment is situated in an ideal location in a quiet, beautiful neighborhood that is close to beaches and a short drive to downtown. Take a quick stroll to the West Falmouth Market or the Shining Sea Bike Path. With easy access to Chapoquoit & Old Silver Beach, this perfectly situated apartment is in an ideal spot for your next Falmouth getaway!