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Thimble Islands vacation rentals

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Top-rated vacation rentals in Thimble Islands

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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

4.95 out of 5 average rating, 180 reviews

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)

Top guest favorite

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

4.99 out of 5 average rating, 496 reviews

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.

Top guest favorite

Apartment in Milford

4.97 out of 5 average rating, 576 reviews

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!

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

4.95 out of 5 average rating, 221 reviews

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.

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

4.97 out of 5 average rating, 272 reviews

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.

Top guest favorite

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.

Home in Branford

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!

Top guest favorite

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

4.96 out of 5 average rating, 140 reviews

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

Top guest favorite

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

4.99 out of 5 average rating, 102 reviews

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.

Top guest favorite

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

4.99 out of 5 average rating, 109 reviews

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!

Top guest favorite

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

4.94 out of 5 average rating, 268 reviews

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.

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

4.97 out of 5 average rating, 102 reviews

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.

Top guest favorite

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.

Guest suite in Wallingford

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.

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Popular amenities for Thimble Islands vacation rentals

Laptop-friendly workspace

Air conditioning

Thimble Islands house rentals

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.

Home in Branford

4.83 out of 5 average rating, 54 reviews

King Suite with Private Bath and Private Entrance

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

4.96 out of 5 average rating, 222 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Home in Coventry

4.98 out of 5 average rating, 113 reviews

Cozy cottage 5 minutes from UConn

Top guest favorite

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.

Home in Branford

4.95 out of 5 average rating, 110 reviews

Charming home, easy access to everything Branford

Top guest favorite

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

4.95 out of 5 average rating, 113 reviews

Beach Haven - waterfront, near Yale, sunsets

Top guest favorite

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

5 out of 5 average rating, 23 reviews

Marina Chic: Bright Seaside Gem

Top guest favorite

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

5 out of 5 average rating, 19 reviews

Coast and Country Private Estate

Top guest favorite

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.

Home in Branford

4.98 out of 5 average rating, 40 reviews

The Eagle- Private Beach

Other great vacation rentals in Thimble Islands

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

5 out of 5 average rating, 10 reviews

Beachfront Cottage Serene Private Beach, Kayaks

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

4.96 out of 5 average rating, 91 reviews

Pristine Carriage House Apartment Downtown

Top guest favorite

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

5 out of 5 average rating, 44 reviews

Fully Renovated Rural Barn

Top guest favorite

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

5 out of 5 average rating, 26 reviews

Branford Coastal Bungalow

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

4.97 out of 5 average rating, 77 reviews

The Barn by the Sound

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

Top guest favorite

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

4.95 out of 5 average rating, 38 reviews

Studio Cottage

A serene outdoor space features a gravel pathway bordered by lush greenery and decorative rocks. A chair is positioned on the path, offering a quiet spot for relaxation. Ferns and hostas complement the natural setting, enhancing the connection to the surrounding trees.

Loft in Killingworth

4.93 out of 5 average rating, 60 reviews

A Peaceful Perch

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