Thimble Islands vacation rentals

4.95 out of 5 average rating, 180 reviews

A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.

Cottage in Guilford

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

4.99 out of 5 average rating, 496 reviews

A modern living space features a comfortable sofa, a circular coffee table, and a television unit. Large sliding glass doors create a seamless view of the outdoors, with natural greenery visible beyond the private deck. Soft natural light fills the room, enhancing its inviting ambiance.

Guesthouse in Guilford

Get Back to Nature at a Modern Wood Clad Getaway

SPRING IS HERE--Glorious spring birds. Come and enjoy a wonderful time in our guest house--warm days, cool nights. You can Hike on the trails, and Stroll along the ocean. Ospreys; hawks; cardinals, blue jays, bluebirds, gold finches and more are here year round. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

4.97 out of 5 average rating, 578 reviews

Apartment in Milford

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

4.95 out of 5 average rating, 222 reviews

A striking lake scene captures a vibrant sunset, with vivid hues of red and purple reflected on the calm water. The surrounding shoreline is lined with trees silhouetted against the colorful sky, offering a serene and picturesque view.

Home in East Haddam

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

4.97 out of 5 average rating, 273 reviews

The spacious living area features high ceilings with exposed beams, large bay windows, and a comfortable seating arrangement. Natural light floods the room, highlighting the hardwood floors and greenery from a potted plant. A television is positioned beside a wooden cabinet.

Apartment in New Haven

The Pearl, New Haven

Amazing hidden luxury experience along the Quinnipiac River in a historic mid-19th century property. Enjoy the scenic river and sunset views, soak in our stunner claw-foot tub, recharge in the sunlit living room, work in the dining alcove, or relax by the bay windows with your favorite drink. NO KITCHEN, but we have a coffee maker, tea kettle, toaster oven, microwave, fridge, plates, and cutlery. We are 15 mins drive from Yale, 2 mins walk to the downtown bus, and easy cycling downtown.

An open living space is visible, featuring a modern kitchen area with white cabinetry and a black countertop. A comfortable sofa is positioned in front of a large window, providing natural light. Decorative plants enhance the inviting ambiance of the room.

4.98 out of 5 average rating, 155 reviews

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

4.96 out of 5 average rating, 141 reviews

An outdoor seating area is featured in front of a modern structure, surrounded by lush greenery. Comfortable chairs encircle a stylish fire pit, while warm lights hang above, enhancing the inviting atmosphere. Stone pavers lead towards an expansive open area, promoting a seamless indoor-outdoor connection.

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

4.99 out of 5 average rating, 102 reviews

A cottage is nestled in a green lawn, bordered by a wooden fence. Tall trees frame the structure, which features a combination of shingles and large windows. The nearby water is visible, reflecting the clouds and sky, adding to the serene ambiance.

Cottage in Guilford

Waterfront Joshua Cove Cottage with private beach.

Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

4.99 out of 5 average rating, 109 reviews

A lively waterfront scene features colorful Adirondack chairs arranged around a fire pit. Guests can be seen enjoying the sunset, with vibrant orange and pink hues filling the sky. A rustic building and dock are visible in the background, adding to the inviting atmosphere.

Apartment in Branford

Downtown Branford Retreat - Quiet yet Central Apt

A welcoming apartment nestled in the heart of Branford - a quintessential shoreline community! This inviting space offers modern design, a well-equipped kitchen, comfortable bedroom, and a convenient location. Situated within walking distance of the town green and minutes from beaches, guests can easily explore this vibrant shoreline town. From boutique shops and art galleries to charming cafes and trendy restaurants, experience the best of Branford right at your doorstep!

4.94 out of 5 average rating, 268 reviews

An aerial view captures the cottage's proximity to the beach, with sandy shores and gentle waves visible. The surrounding area features a blend of trees and homes, enhancing the scenic coastal environment.

Cottage in Guilford

The Cottage at Indian Cove

A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.

4.97 out of 5 average rating, 102 reviews

A wooden playset is situated in a spacious backyard, featuring a slide, swings, a climbing structure, and a fort-like space with a roof. Surrounding it are tall evergreen trees, adding a natural backdrop to the play area. The ground is covered in wood chips for safety.

Guesthouse in Madison

Beachy & Bright Coastal Escape - 5 Mins to Beach

Charming coastal guesthouse in Madison’s historic district—just a 5-min walk to a private beach, 5-min drive to town, and 20 mins to New Haven. Bright, beachy, and newly renovated with a king bedroom, full kitchen, private deck, and huge backyard. Set on nearly an acre in the heart of New England, it’s perfect for couples, families, and girls’ getaways. Walk to cafes, shops, and the iconic RJ Julia bookstore.

Guest suite in Wallingford

A lush garden space is surrounded by vibrant greenery and flowering plants. A brick patio features a red umbrella over a small table and chairs, providing a shaded area for relaxation. Decorative planters enhance the tranquil setting, inviting guests to enjoy the outdoors.

5 out of 5 average rating, 591 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Thimble Islands vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Thimble Islands house rentals

Superhost

A spacious bedroom features a king size bed adorned with a patterned quilt and two decorative pillows. Light hardwood flooring contrasts with the pale grey walls. A vintage turquoise refrigerator and a dresser with multiple drawers are visible, while natural light streams in through two windows.

4.83 out of 5 average rating, 54 reviews

King Suite with Private Bath and Private Entrance

PaulaRating, 5 stars1 month ago

Great location, just down the street from the beach! Branford was a short drive, great shops and restaurants.

4.96 out of 5 average rating, 222 reviews

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

Designer Beach Retreat on Exclusive Cedar Beach

SaraRating, 5 starstoday

We had a great stay! Incredible one-of-a-kind view over the marsh. We saw so many different beautiful sea birds and an incredible sunset. Very short walk from the beach. Great place to stay with young kids. Well stocked kitchen with supplies and basic seasonings. Would return! Very cozy great family getaway! There are extensive requirements for clean up upon check out.

4.98 out of 5 average rating, 113 reviews

Home in Coventry

Cozy cottage 5 minutes from UConn

JdRating, 5 stars2 days ago

Immaculate space. Location and views are incredible. Check in was easy, hosts were very communicative and you can tell they put a great deal of energy into their home. They also included fresh eggs from their farm. We were obsessed with it and will definitely rebook.

A comfortable living area features a light-colored sofa accompanied by two lamps on side tables. A textured area rug lies beneath a coffee table, while natural light filters through multiple windows, creating a bright and open space. A dining area is visible in the background.

4.95 out of 5 average rating, 111 reviews

Charming home, easy access to everything Branford

KatyRating, 5 stars1 month ago

super nice place. comfortable beds. Great backyard. super responsive and friendly hosts. Will book again!

4.95 out of 5 average rating, 113 reviews

A vibrant sunset reflects on calm waters, with shades of orange and purple illuminating the sky. Silhouettes of small boats are visible along the sandy shoreline, while gentle waves create a serene atmosphere. The scene offers a tranquil view of Long Island Sound at dusk.

Home in New Haven

Beach Haven - waterfront, near Yale, sunsets

Lauren RRating, 5 stars1 week ago

My family and I had such a wonderful stay at this house. The house was immaculate and well stocked for our stay. Matthew and Celia are great hosts. We really appreciated the basket of snacks and dog cookies that were left for us and our fur babies (Thank you!). They truly thought of everything and it felt like “home” the entire time we were there. The views from the back deck are truly spectacular. We spent many hours sitting in the sunroom and out on the deck enjoying the sights. My pups enjoyed daily walks at the sea wall park that was steps from the house. I can’t say enough great things about our stay. Thanks to our hosts for sharing their beautiful home with me and my family.

5 out of 5 average rating, 23 reviews

An aerial view displays the modern home surrounded by greenery, with the marina and water visible in the background. Nearby streets and houses can be seen, showcasing the coastal setting and convenient access to recreational areas.

Home in Guilford

Marina Chic: Bright Seaside Gem

NicholeRating, 5 stars2 weeks ago

Lauren was probably the best host we have had on Airbnb. So responsive and helpful and the place was amazing. Guilford is a special place and we will definitely be back and stay here. Awesome property!

5 out of 5 average rating, 19 reviews

A modern home is showcased with a stone foundation and large windows, allowing natural light to fill the space. A spacious deck is visible, featuring colorful seating options and a stone wall that surrounds a well-maintained lawn, complemented by leafy trees.

Home in Guilford

Coast and Country Private Estate

AndreaRating, 5 stars5 months ago

Suzanne’s home is beautiful and felt like being in our own home. The property is serene and very private. The house and kitchen were well equipped for cooking. Suzanne was so easy to communicate with pre during and post stay. We have family in the area so I hope to be back again.

A gated entrance leads to a sandy path towards the beach, with a serene view of the water. A small island can be seen in the distance, framed by a clear blue sky. Surrounding vegetation adds a touch of greenery to the scene.

4.98 out of 5 average rating, 40 reviews

The Eagle- Private Beach

StephanieRating, 5 stars2 weeks ago

Great location with private beach access. Cozy 2-bedroom slept our family of 4 comfortably. Comfortable beds, great shower pressure, and large yard out back. I’m originally from Branford and we visit my parents regularly. Will definitely keep Abigail’s home in mind for future visits!

Show all

Other great vacation rentals in Thimble Islands

5 out of 5 average rating, 10 reviews

A screened-in porch features large paneled windows offering expansive views of the waterfront. A cozy seating area with a blue couch and a wicker table is positioned against the wooden walls. Natural light fills the space, highlighting the warm hardwood flooring.

Cottage in Branford

Beachfront Cottage Serene Private Beach, Kayaks

BasilRating, 5 stars9 months ago

We loved it. Redefines “fully stocked” - David’s place had everything we could ask for. The water at high tide was magical. Kayaking, fishing and we found over 100 (literally) hermit crabs.

4.96 out of 5 average rating, 91 reviews

A well-maintained garden features raised wooden beds filled with a variety of plants. A wooden trellis supports climbing greenery, while sunlight filters through the trees, casting gentle shadows across the manicured lawn.

Barn in Guilford

Pristine Carriage House Apartment Downtown

LindaRating, 5 stars2 months ago

Wonderful location- easy walk to town! Fun carriage house garage apartment.

5 out of 5 average rating, 44 reviews

A newly renovated barn features a dark exterior with large windows on both levels. A gravel patio area is surrounded by low shrubs, providing a space with a table and chairs for outdoor dining. Lush green trees frame the serene setting.

Barn in Roxbury

Fully Renovated Rural Barn

XenaRating, 5 stars3 weeks ago

My sister and I stayed at Kevin and Mina’s beautiful barn for 5 days. It was the perfect home base as we traveled through the neighboring towns on the Gilmore Girls trail. The house itself was specious, clean, well-decorated, and comfortable. It was great having the flexibility of enjoying the natural sunlight with the skylights open during the day and being able to sleep in a little with them closed overnight. Would definitely stay here again!

5 out of 5 average rating, 26 reviews

A panoramic view of the coastline captured under a blue sky with scattered clouds. The serene water reflects the light, while a sandy beach curves along the shore, lined with coastal homes and greenery in the distance. The tranquil scene embodies waterfront living.

Apartment in Branford

Branford Coastal Bungalow

MarkRating, 5 stars2 weeks ago

Terrific stay in a great neighborhood.

4.97 out of 5 average rating, 77 reviews

A sandy beach stretches under a clear blue sky, with gentle waves lapping at the shore. Weathered wooden fencing outlines the beach, while sparse grasses dot the sandy landscape, contributing to a serene coastal scene.

Guesthouse in Madison

The Barn by the Sound

DianeRating, 5 stars3 weeks ago

Vicky and Peter's little barn apartment was perfectly located for us, close to the beach and we so enjoyed their well landscaped and beautiful property, the birds in the trees and views out the window. The furniture and bed were comfortable and kitchen had all that we needed. They thoughtfully left us a six pack of nice water in the fridge and a pretty little bouquet of her garden flowers on the table. Vicky was friendly and gracious when we saw her in her yard and ready to assist if we needed any thing. They also made the effort to move patio furniture to a location for our use. I would definitely recommend Vicky and Peter's airbnb for others.

Superhost

A fire pit made of black metal is positioned on a stone patio, facing the expansive water view. Surrounding the patio, a wooden railing creates a barrier, complementing the calm atmosphere. Grey clouds can be seen over the serene water, suggesting a peaceful setting.

Home in Hampton Bays

4.84 out of 5 average rating, 68 reviews

Hamptons Oceanfront Oasis

LaurelRating, 5 stars2 days ago

Such a cute little place and Tasha was very responsive. She took care of all our needs as soon as we reached out. Would highly recommend!

4.95 out of 5 average rating, 38 reviews

A tranquil beach scene captures a curved shoreline meeting calm water, with soft sand and scattered seaweed. The sky is painted in warm hues of orange and purple, reflecting on the surface of the water. Silhouettes of distant rocks and small landmasses are visible on the horizon.

Guesthouse in Clinton

Studio Cottage

KellyRating, 5 stars2 days ago

Looked just like the photos. Private space. Clean and tidy, had a few essentials including coffee! She was very responsive and gave East to follow directions for checking in. Provided great recommendations for nearby places. Location was exactly what we were looking for. Would highly recommend.