Thimble Islands vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Thimble Islands

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

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Superhost

Home in Roxbury

5 out of 5 average rating, 10 reviews

Zoom In Map To 5*Roxbury "Painter Hill" PoshPadsCT

PoshPadsCT - Private 4-5-Bedroom hilltop retreat on a serene brook - a perfect getaway. New Hot Tub, Terrace, Trampoline. Located on a 3 acre property near historic estates, Maple Bank farm stand and Toplands Farm and just 1.5 hours from NYC. The house features beautiful fields, views, a large terrace with a gas grill, a firepit. Nearby hiking trails & Washington restaurants, shopping, distilleries, vineyards, breweries, and more! Ski Mohawk Mountain or Swim Lake Waramaug State Beach.

Guest favorite

Chalet in Goshen

4.89 out of 5 average rating, 142 reviews

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & stunning woods view, 10 minute drive to Woodridge Lake.

Superhost

Two comfortable chairs are positioned on a spacious porch, offering a clear view of the beach and ocean. The horizon is visible in the distance, with calm waters under a blue sky dotted with clouds.

Home in West Haven

4.79 out of 5 average rating, 43 reviews

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

Top guest favorite

A serene indoor hot tub is surrounded by wooden paneling and natural stone accents. Soft blue lighting illuminates the water, while greenery is positioned nearby, enhancing the calming ambiance of the space.

Condo in Norwich

4.98 out of 5 average rating, 135 reviews

The Vacay Villa

The Vacay Villa, just minutes away from Mohegan Sun, Foxwoods and The Spa at Norwich Inn, offers so many amenities you won’t even have to leave the grounds. Private balcony, fireplace, two outdoor pools currently open, year-round access to luxurious hot tub and saunas, small workout room, laundry facilities, pub and upscale restaurant allow for a one-of-a-kind stay at an incredibly affordable price. Why spend hundreds to stay at the area casinos when you can stay in your own private villa?

Top guest favorite

A spacious outdoor dining area features a large wooden table surrounded by matching chairs. Sunlight illuminates the area, showcasing a well-maintained yard with a manicured hedge and a small garden shed visible in the background.

Home in Northport

4.94 out of 5 average rating, 114 reviews

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

Superhost

A spacious living room is defined by a sectional sofa, complemented by a wooden coffee table at the center. Natural light filters through large windows adorned with sheer curtains. Light-colored walls and decorative wall art enhance the inviting ambiance.

Home in East Hampton

4.83 out of 5 average rating, 6 reviews

Cozy Town Cottage - Minutes from EH Town

This charming, historic home is perfect for a young family! The original mudroom with laundry, farm kitchen (no dishwasher), spacious dining and living rooms, two bedrooms and one bathroom welcome you on the main level. Upstairs is a larger bedroom and a second bathroom as part of an open primary suite. Take a half mile, tree-covered walk to town, or stop at the grocery store or restaurants just down the street. Sorry but, absolutely no animals as owner has severe allergy.

Guest favorite

A charming building is illuminated by soft evening light, surrounded by blossoming trees adorned with twinkling lights. Outdoor seating is visible, inviting guests to enjoy the vibrant atmosphere of the town. The sky transitions to a serene twilight blue, enhancing the scene.

Guest suite in Branford

4.9 out of 5 average rating, 100 reviews

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

Guest favorite

A covered outdoor seating area is furnished with a combination of turquoise and brown seating, complemented by decorative pillows. Soft lighting from string lights enhances the space. A swing seat is positioned against the wall, and a small table is centered on the tiled patio.

Home in Mastic

4.89 out of 5 average rating, 105 reviews

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Guest favorite

A view of the Peconic River is depicted from a wooden deck, featuring a small round table and two woven chairs. The water reflects clear blue skies, with boats visible in the distance and trees lining the shore.

Houseboat in Riverhead

5 out of 5 average rating, 11 reviews

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

Superhost

An outdoor deck area is seen featuring a large round table surrounded by several comfortable chairs. A sun umbrella provides shade, while a propane grill is positioned nearby. Lush trees create a natural backdrop, enhancing the serene atmosphere of the space.

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Top guest favorite

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

Home in Greenport

4.98 out of 5 average rating, 179 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Guest favorite

A spacious outdoor deck features a hot tub and comfortable seating area, surrounded by lush greenery. The inviting hot tub offers a relaxing retreat, while the seating includes a large sofa and a coffee table, creating an ideal space for outdoor gatherings.

Home in Montauk

4.92 out of 5 average rating, 51 reviews

Montauk Family Gem: HotTub, Pro Kitchen, Fireplace

Escape to your perfect Montauk getaway! Nestled on a secluded, beautifully landscaped lot at the end of a quiet dead-end street, this recently renovated 4-bedroom, 3.5-bathroom beach house offers the ultimate combination of luxury, comfort, and privacy. We are also pet friendly!