Holiday houses in Block Island Sound

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Top-rated holiday rentals in Block Island Sound

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Top Guest favourite
A monochromatic logo features two fish intertwined, symbolizing the property name 'Heathers on High Street' and the location 'Westerly, RI.' The design is clean and simple, with the word 'AIRBNB' clearly displayed below.
Apartment in Westerly
4.99 out of 5 average rating, 119 reviews

Heathers On High Street King Bed/Twin Bed

Experience Westerly life like a Local! Enjoy this centrally-located Apartment close to Downtown. Easy highway access to the Beach and Casinos. Free Parking with Private entrance opens to a courtyard with Gazebo Sitting area and a Grill just for you! The 2 Bedroom Apartment is located on the 2nd floor with a Full Kitchen/Living Room combination, 1 Bathroom, Washer/Dryer and Central Air. The Master Bedroom has 1 King Bed with a new Nectar Mattress. Second smaller bedroom has a Twin Pillowtop Bed

Top Guest favourite
An inviting living area is displayed, featuring high cathedral ceilings with exposed wood beams. A cozy couch faces a television, while a beautifully decorated Christmas tree adds festive charm. Soft lighting creates a warm ambience, inviting relaxation and gatherings.
Cabin in Westerly
5 out of 5 average rating, 155 reviews

Fireside Delights & Snowy Nights - Sleeps 7

WINTER GETAWAY ALERT: Cozy up on the RI Coast! Welcome to Woodhaus Westerly — a peaceful winter retreat minutes from downtown shops, breweries, and coastal walks. Enjoy 3 private wooded acres for starry-night bonfires, winter trails, and cozy nights by the wood stove with blankets, games, and movies. Dog + kid friendly with plenty of space to relax. Perfect for couples, families, or a remote-work refresh. ☀️Beach Pass returns for Summer 2026! View more photos and updates @Woodhaus_Properties

Top Guest favourite
An open living area features warm wood flooring and a working fireplace framed by a wooden mantel. Two comfortable chairs sit beside a small table, while a spacious red sofa is positioned nearby. A well-equipped kitchen is visible in the background, with modern appliances.
Cottage in Mystic
4.98 out of 5 average rating, 266 reviews

Mystic Cottage Retreat, near downtown

This recently renovated cottage is at the top of a quiet lane with a sweeping meadow view. Single level. Two bedrooms sleep four (queen and two twin beds); new, well-equipped kitchen and one bath, open living area, deck and patio. Light and spacious. Working fireplace, central A/C; W/D; expanded cable TV and wifi; off street parking for two cars. Market/deli nearby; pleasing walk (less than a mile from center of Mystic)- restaurants, shops, marinas, etc. Near Amtrak station. Great retreat!

Top Guest favourite
Guesthouse in Westerly
4.99 out of 5 average rating, 115 reviews

Ocean Shire Coastal Retreat + Beach Pass

Relax at this warm modern private coastal cottage. Located 3 miles of Misquamicut and Watch Hill beaches. Season beach pass included. Kids Welcome! 1100 sq. ft, two bedroom, 1.5 bath attached cottage on 1.4 acres. Taylor Swift's Watch Hill home: 3 miles Ocean House Watch Hill: 3 miles Mystic, CT: 10 miles Newport, RI: 38 miles Wooded yard is a beautiful tranquil outdoor space. Easy access to shops, restaurants, bars, sailing, water sports and beach are all available at your door.

Top Guest favourite
A cozy cottage exterior is showcased, featuring a gabled roof and wooden siding in earthy tones. A spacious screened porch with rocking chairs invites relaxation, while a nearby shed complements the rustic aesthetic. Surrounding nature highlights seasonal foliage, enhancing the tranquil setting.
Home in Stonington
4.96 out of 5 average rating, 202 reviews

Romantic Seaside Cottage in Mystic

This cozy seaside cottage with sleep loft has the look and feel of an old classic yacht inside with modern amenities. Couples will love the water views, screened porch, gas-wood stove, heated stone floor in cedar bathroom, outdoor shower and patio. Another larger 2 bedroom cottage on property is for rent also for families with younger children. This rental is NOT suitable for toddlers or children under 12 due to the open balconies, railings and narrow spiral staircase to the loft.

Top Guest favourite
Guest suite in Stonington
4.99 out of 5 average rating, 336 reviews

Morgan Suite - spacious | hot tub | water views!

The Morgan Suite is a private Airbnb located in a quiet neighborhood along the Pawcatuck River. Just minutes to downtown Westerly, downtown Mystic, beaches, breweries, wineries, shops, restaurants and much more. This Airbnb a perfect for a romantic getaway or a relaxing memorable vacation with a friend. If you are looking to explore a new area and relax, the Morgan Suite is for you! The home is spacious, newly renovated with excellent amenities. Newly added - hot tub and massage chair!

Top Guest favourite
The exterior of the cottage is visible, showcasing a light grey facade with white trim. A paved driveway accommodates a parked car. A large tree provides shade, and an American flag hangs near the entrance. A spacious lawn is present, bordered by a fence.
Cottage in Groton
4.96 out of 5 average rating, 254 reviews

EASY BEAT

LOVELY MID 1800'S COTTAGE Located in the historic Groton Bank neighborhood. Close to beaches, casinos, walking distant to EB. Short drive to Pfizer, Coast Guard Academy, Connecticut College, US Submarine Base and minutes to downtown Mystic. This property is a one bedroom one bath with a single pullout couch in bedroom and living room. Offers a spacious outside lawn with patio. Lots of off street parking. Fenced yard for pets. New Central Air and heat. Washer, dryer, grill and fire pit.

Top Guest favourite
A spacious dining area is highlighted by a wooden table surrounded by elegant chairs. Natural light pours in through large windows, illuminating the inviting living space with a comfortable sectional couch and a wall-mounted TV. Decorative pendant lights enhance the modern kitchen's open layout.
Home in Westerly
4.97 out of 5 average rating, 156 reviews

Cheerful Cozy Colonial

Relax at this warm, welcoming, peaceful place to stay, with hiking trails nearby and only a 10-15 minute drive to various beaches, and a 10-minute drive to downtown Westerly. Set on 2+ acres, rejuvenate and connect with friends and family around the outdoor fire pit. Inside you will find a comfortable space with a full kitchen, living room, dining room, three bedrooms, and a full and half bath. In the warmer weather, enjoy the outdoor shower after a long hike or trip to the beach.

Top Guest favourite
A serene bedroom features a spacious bed adorned with soft grey linens. Two bedside tables, each with a lamp, flank the bed. A vibrant piece of artwork and a framed print add color to the walls, enhancing the room’s inviting ambiance.
Guest suite in Westerly
4.98 out of 5 average rating, 163 reviews

Private suite close to beaches and downtown.

The Ruedemann Suite is situated off of our main house in a quiet neighborhood. We are located 3 miles from Misquamicut Beach & Watch Hill. Historic Downtown Westerly with its thriving restaurant, arts & music scene is 1.5 miles from the house. Take a short drive to Stonington or Mystic for shopping or local vineyards. Feeling lucky? Mohegan Sun & Foxwoods Casinos are close by! Newport & Providence are a 45-minute drive. Follow on the gram @ruedemannsuite

Top Guest favourite
A spiral staircase with a sleek black railing leads to the loft bedroom. A mirror with a burgundy frame is mounted against the wall, reflecting the light. The open living area features a light-colored couch and a wooden dining table, visible through large windows offering views of the outdoors.
Guesthouse in Mystic
4.98 out of 5 average rating, 670 reviews

Gorgeous Waterfront Getaway

Perfect getaway from the city for couples wanting peace and tranquility and stunning views. A beautiful waterfront one bedroom guesthouse, one and one-half miles from downtown Mystic CT. Beautifully decorated with art and antiques. Kitchenette, full bath and loft bedroom. Queen bed. Air conditioning and heated. Belgian linen bedding! Private patio. Dock. Kayak/Canoe rentals close by. Internet.

Top Guest favourite
Tiny home in East Lyme
4.99 out of 5 average rating, 120 reviews

Waterfront Bliss Tiny Home

Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!

Top Guest favourite
A charming cabin with a red exterior sits surrounded by colorful autumn foliage, reflecting on the calm surface of a pond. A spacious deck is visible, featuring a patio chair and table, while a kayak rests nearby on the grassy shore.
Cabin in North Stonington
4.96 out of 5 average rating, 244 reviews

Come to the woods and snuggle in front of the fire

Come to the woods of Southeastern Connecticut and enjoy some solitude and connection in the woods while wrapped in our flannel LL Bean bathrobes. Snuggle with a glass of wine or coffee by the fire and unplug, rest, and rejuvenate with your partner or by yourself. Only fifteen minutes away from casinos, shopping or restaurants in Mystic or downtown Westerly, RI.

Popular amenities for Block Island Sound holiday rentals