Guesthouse vacation rentals in Nantucket

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Top-rated guesthouse rentals in Nantucket

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite
The cottage's entrance features a charming screen door framed by flowering plants in a wooden box. A small wooden table with two chairs is set for dining, with wine glasses and a potted plant placed center stage. A bicycle leans against the side.
Guesthouse in Siasconset
4.93 out of 5 average rating, 107 reviews

Sweet Dreams Romantic Guest Cottage.....'Sconset

This Cottage is Limited for a Couple !!! Non Smoking-No pets-No Children Check In 3 pm (but you can always leave your luggage earlier) Check Out 10:30 (Luggage may be left to retrieve later) Sweet Dreams is a lovely two-story free-standing building next to my home, outside table & Gas Grill, A chair for relaxing or reading. Beach chairs and towels also supplied. The center village & beach 4-minute walk Most likely you can hear the crash of ocean waves nightly Central heat/air Flat Screen TV

Guest favorite
A patio dining area is set with a glass table and four wicker chairs. A bottle of wine stands at the center, accompanied by two glasses and two plates. Surrounding greenery creates a natural backdrop, enhancing the serene outdoor dining experience.
Guesthouse in Edgartown
4.92 out of 5 average rating, 26 reviews

Private cabin in Wildlife Habitat; near bus route

Come to “Simple Sea-Renity”, a private cabin on Martha's Vineyard. Located in a half acre certified wildlife habitat, this air conditioned cabin offers lots of privacy while keeping your stay simple & back-to nature. You have your own small yard & a patio for dining, napping or stargazing -enclosed outdoor shower (toilet is indoors) -TV -wifi -gas grill -scullery sink -refrigerator/freezer -microwave -coffee maker Centrally-located in Edgartown, an easy walk to Sengekontacket or VTA routes

Top guest favorite
A bright living area features a comfortable seating arrangement with soft, neutral-toned couches. Natural light fills the space through multiple windows, and a rustic wooden coffee table enhances the cozy feel. A small dining area is visible in the background.
Guesthouse in Edgartown
5 out of 5 average rating, 24 reviews

THE BIG CHILL ~ ONE MILE TO EDGARTOWN CENTER

The Big Chill is close to the buses, grocery stores, fish markets, Morning Glory Farm, the beautiful beaches and the center of Edgartown. You’ll love it.. its cozy, has A/C, you'll love the high ceilings on the second floor and the location! The BIG CHILL has a full bath indoors and a fully enclosed outdoor shower steps from the door. Great for couples, solo adventurers, and business travelers….a bike ride to town. If you need a bigger house, check out Sandy Feet Retreat for 5-10 guests.

Guest favorite
A well-lit bedroom features a spacious bed with white linens and decorative pillows. Natural light enters through two windows adorned with blinds. A soft area rug is positioned under the bed, complementing a cozy reading nook with a rattan chair and a bean bag.
Guesthouse in Edgartown
4.95 out of 5 average rating, 44 reviews

Wedding RetreatTrails Golfing Beaches Private Gem

✨ LOCATION, LOCATION✨ ✅Cleanliness, Fully stocked kitchen ✅Pet-Friendly, Minutes from ferry & beaches ✅ Peaceful & private neighborhood 🌳 Hidden trails—Great for exploring 🏡 Perfectly Getaway, ✅ Easy access to all towns, Hassle-free stay. 🚗 Just 8 minutes to local markets, and top-rated restaurants. 🚴‍♂️ A scenic 13-minute bike ride takes you to the charming Edgartown Village or Katama South Beach—perfect for breathtaking sunsets! Convenience, comfort, and nature at your doorstep.

Guest favorite
A bright living area features a light-colored sofa adorned with soft throw pillows, facing a round coffee table. Large double doors open to a private outdoor space, where a cozy seating area is visible. Natural light illuminates the room, enhancing the airy atmosphere.
Guesthouse in Nantucket
4.92 out of 5 average rating, 13 reviews

Beach Chic Guest Cottage, Town

Your perfect seaside Nantucket getaway is our idyllic guest cottage in town, on the corner of historic Orange Street and Dover. Lovingly restored and fully styled in coastal chic, this 1900 built guest cottage with private outdoor garden lounge is completely renovated with all the appointments. Open 1 bedroom loft with double bed upstairs, plus a twin xl daybed in living room on first floor, large sofa, full bathroom, mini fridge, coffee maker, microwave, living room, outdoor living room.

Guest favorite
A charming two-story exterior is seen, featuring weathered shingles and a light-colored door. Lush greenery, including a hydrangea bush, surrounds the base of the building, enhancing the natural setting. Windows allow for natural light, while a small shed is visible on the side.
Guesthouse in Nantucket
4.94 out of 5 average rating, 87 reviews

In-Town Private Cottage w/ parking

5-min. walk to Town, w/ parking. Upstairs bedroom w/ 2 twin beds, queen pull-out couch in main living area w/TV. Bathroom w/ shower. Small kitchen area w/ fridge, microwave, coffee pot, sink (no stove). Enclosed outdoor shower, all linens, bath towels, beach towels, beach chairs and cooler. Heat/AC/Wi-Fi. PLEASE NOTE: All rentals beginning after July 1, 2019 are subject to new state and local taxes of 11.7% on total rental, collected separately by airbnb after the booking.

Top guest favorite
Guesthouse in Vineyard Haven
4.95 out of 5 average rating, 136 reviews

West Chop Cottage + Beach Access

Sweet, rustic, and tiny - yet comfortable with all the amenities - the cottage is a short walk to the town center, lighthouse, landmarks, and lovely harbor beaches on desirable West Chop. The private yard with harbor view allows for sunbathing and stargazing, lounging and lawn games, grilling and campfires. With access to spectacular private association ocean beach, Hancock Beach, on the island's south shore in Chilmark, this rental offers a complete Vineyard experience.

Top guest favorite
A bright living area features a striped couch adorned with a 'SUMMER HOUSE' pillow, complemented by a cozy armchair. Natural light enters through windows with white blinds, and wooden beams add a touch of character. A decorative coffee table sits in the center, enhancing the inviting space.
Guesthouse in Barnstable
4.9 out of 5 average rating, 70 reviews

Osterville Guest House

Charming 600 sq. ft. guesthouse located in the desirable village of Osterville. Take a short walk down Main Street for some shopping or dining. Along the way you may want to stop at Gone Chocolate for an ice cream or Dunkin Donuts for a quick coffee. You will have your choice of several restaurants to dine at including Five Bays Bistro, Crisp Flatbread Inc., Wimpy’s Seafood Market, or the newest restaurant in Osterville- the Chart Room at Crosby’s boat yard.

Top guest favorite
A charming cottage exterior features a shingle facade and a spacious wooden deck. Two lounge chairs are arranged invitingly beside a potted plant. Large glass doors offer a view into the interior, while a grill is positioned nearby for outdoor cooking.
Guesthouse in Madaket
4.96 out of 5 average rating, 108 reviews

Madaket Bright and Airy Guest Cottage

Escape to this charming guest cottage in Madaket, just a short walk from Madaket Beach, known for its stunning sunsets. This peaceful retreat offers a cozy, light-filled space with a well-equipped kitchen and comfortable sleeping arrangements. Enjoy mornings on the private patio, bike scenic paths, or dine at Millie’s. Easily explore Nantucket’s shops, restaurants, and history. End your day with a breathtaking sunset—your perfect island getaway awaits!

Top guest favorite
A dining area is presented with a rustic wooden table, set for a meal. Four dark chairs surround the table, and a vase of white flowers adds a touch of decor. The adjacent living area features a comfortable sofa, flanked by windows allowing natural light.
Guesthouse in Oak Bluffs
4.99 out of 5 average rating, 98 reviews

Mermaid Cottage

Our735 square foot guest cottage is spacious and has a contemporary beachy feel. We are located near the ferries, buses, bike path and a short walk to a public beach. We've tried to provide everything you'll need for a comfortable stay on Martha's Vineyard. The house has a front porch, outdoor dining, hot tub and central air.

Guest favorite
Guesthouse in Edgartown
5 out of 5 average rating, 35 reviews

La Casita

After years of hard work ,planning downsizing from the main house the casita was built and completed to full fruition. Environmentally green household (composting, recycling, clothesline, minimal trash, etc.) Enjoy refuge,quietness ,comfort ,simplicity of living ,and proximity to all the island offers!

Top guest favorite
The exterior of the cottage is showcased, featuring a shingled facade and large windows that provide ample natural light. Lush greenery is present in the foreground, with ornamental grasses swaying gently. A vehicle is parked nearby, highlighting the cottage's easy accessibility.
Guesthouse in Madaket
4.99 out of 5 average rating, 88 reviews

Beautiful Nantucket Summer rental

Lovely newly built cottage in Fishers Landing, with an open floor plan with living room, dining area and fully equipped kitchen and powder room. Second floor, bedroom with king bed,and second bedroom with twin beds. Full bath Laundry room with washer and dryer. Garden with patio and outdoor shower

Popular amenities for Nantucket guesthouse rentals

Quick stats about guesthouse rentals in Nantucket

  • Total vacation rentals

    Explore 10 vacation rentals in Nantucket

  • Nightly prices starting at

    Nantucket vacation rentals start at G$41,785 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,060 verified reviews to help you choose

  • Wi-Fi availability

    10 of Nantucket vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Nantucket rentals

  • 4.9 Average rating

    Nantucket stays are highly rated by guests—averaging 4.9 out of 5!