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

A serene beach view features soft sandy shores leading to calm waters. A small wooden bench is positioned in the foreground, while a sailboat glides gracefully on the horizon. Gentle waves can be seen lapping at the shoreline under a clear blue sky.

Home in Milford

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

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 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 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, 99 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

An open kitchen space features modern appliances, including a stainless steel stove and ample counter space. Barstools are positioned at a breakfast bar, while natural light illuminates the area through several windows. Warm wood flooring complements the neutral-colored walls.

Home in Greenport

4.94 out of 5 average rating, 108 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

Guest favorite

A serene lakeside view is captured at sunset, reflecting vibrant colors across the calm water. The shoreline features rocks and grassy areas, with trees framing the scene. A wooden chair is positioned nearby, inviting relaxation while enjoying the natural beauty.

Guesthouse in East Hampton

4.93 out of 5 average rating, 41 reviews

Family-Friendly Lakeside Cottage

Newly renovated lakeside cottage with stunning views. 2 bedrooms with king beds and a pull-out couch, 1.5 bathrooms - 30 second walk to the lake - Fully furnished and equipped - Private rock patio with picnic table and grill - Washer and dryer in unit - Desk for working from home - 2 Kayaks and 2 paddle boards are available for use - Short walk or drive to restaurants, and shops Perfect for romantic getaways, family vacations, or visiting family locally.

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

A sandy beach stretches out under a clear blue sky, with gentle waves lapping at the shore. Beach grass and wooden fencing line the path leading to the water, where a lifeguard stand is positioned for safety.

Home in Hampton Bays

4.82 out of 5 average rating, 67 reviews

Spacious Hamptons Oasis | Perfect for Families

Escape to our stunning year-round retreat in Hampton Bays' Red Creek area. With over an acre of lush land, our charming residence offers unparalleled serenity and tranquility just minutes from local bay, beaches, and wineries. Ideal for family fun, friend retreats, and exquisite dining in the Hamptons. For off-season activities, explore wineries, animal feeding farms, apple and pumpkin picking, breweries, and more. Book now for your dream getaway!

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.

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What guests are saying

Direct Shoreline Long Island Sound Waterfront

4.95 out of 5 average rating, 80 reviews7 months ago

Our visit was utilitarian. We needed accommodations for us, our grown children and grandchildren and a dog. But the site of the cottage, its charm, its comfort made us wish we were staying another week. James' thoughtfulness went beyond any other Airbnb hosts' that we've experienced. Everything we might need if we were staying 10 days was there, clean, labeled. Thank you, James.

Cottage in Guilford

What guests are saying

Stylish Beach Getaway: pool & walking location

5 out of 5 average rating, 9 reviews6 months ago

Maher’s house was an amazing peaceful experience. I enjoyed my time there and he had great recommendations to restaurants and activities! He was very responsive with all questions we had. I will totally stay here in the future if I can get the chance again!! Thank you Maher!!

Home in Southold

What guests are saying

Black Point Retreat - Entertain & Enjoy the Beach!

5 out of 5 average rating, 10 reviews7 months ago

Our group had a wonderful stay at this beautiful, spacious home. It was spotlessly clean and well stocked with supplies. The 7 of us enjoyed gathering around a spacious table to play games in the bright roomy sunroom. It led out to a very nice patio with a comfy wicker couch and chairs. The host was very prompt in responding to us and was quick to satisfactorily address our questions. We had a wonderful,memorable time!

Home in East Lyme

What guests are saying

La Sirena Beach Cottage

4.96 out of 5 average rating, 24 reviews3 days ago

House was just as it looked in the pictures - beautifully decorated. Has everything needed for a vacation. Comfortable, bright and cheerful. Back yard was private. House was fully stocked with what was needed along with beach supplies in the outdoor shed. Quick walk to the beach. Would easily rent again!

Home in Milford

What guests are saying

The Sandy Shack - Coastal Escape

4.9 out of 5 average rating, 21 reviews6 days ago

As a native long islander I enjoy finding great properties I can bring my family to to take advantage of all long island has to offer. This was the DREAMIEST beach bungalow!! The bedroom with the two beds was just my favorite room especially since we visited off season. You cannot beat this location. I can't wait to book again during high season! Thanks for sharing your home with us !!

Home in Greenport

What guests are saying

Hop Skip and a Jump to the Beach

4.97 out of 5 average rating, 35 reviews8 months ago

Our first ever stay at 'Hop Skip and Jump' really met all of our expectations and needs for the week of 8/10-8/17/24! I have never in my 70+ years of spending a summer week in Old Lyme been so enveloped with 5 star luxury while at the Beach! I would recommend this rental to any small family or a group of girlfriends! Hop

Cottage in Old Lyme

What guests are saying

Seaside Paradise

5 out of 5 average rating, 5 reviews4 months ago

We stay 4 weeks at Jacqueline place, everything was great, did not have any problem. Place is exactly fit the advertising if not better and everything was clean and working. We find place and the area is so peaceful and quiet. Perfect location for someone just looking for rest in very beautiful neighborhood. Jacqueline was very responsive, easy to communicate, helpful and polite. I would definitely stay again and recommend for anyone needs a place feels like home away home.

Home in Milford

What guests are saying

Captains Quarters | July avail!

5 out of 5 average rating, 16 reviews1 month ago

This house served our family very well for a multi-month stay. The house and property are just like the photos and all the amenities were great to have. Would recommend staying here if you are looking for a quiet place near the water in East Hampton. Petra was always very responsive with anything we needed and was an excellent host.

Home in East Hampton

What guests are saying

2 Bedroom Hamptons Waterfront Cottage Rental

5 out of 5 average rating, 21 reviews9 months ago

A quaint cottage that was sparkling clean. Access to the Peconic from a private dock with the available kayaks and canoes. There is a pristine built-in pool with new decking. There was a 10 minute drive to Hampton Bays town with great restaurants, grocery and shopping.

Guesthouse in Hampton Bays

What guests are saying

Newly built twin beach house within steps to beach

5 out of 5 average rating, 8 reviews8 months ago

We stayed here for a wedding at The Burr Mansion, which was extremely close to the house! The house was clean and updated. A few spots to walk to including a local bar. Just a walk to the beach. Bedrooms are all spacious and were very clean. Would definitely stay again.

Home in Fairfield

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