Guesthouse vacation rentals in Block Island Sound

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Top-rated guesthouse rentals in Block Island Sound

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

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Guest favorite

Guesthouse in Stonington

4.97 out of 5 average rating, 223 reviews

True Artist Loft, 5 minutes to downtown Mystic

The Dacha, as it has lovingly been called for almost 80 years was built in 1945 originally as a studio for the artist that resided on the property. The unique structure is truly one of a kind, fully insulated for winter and tucked away from the road, sitting on a quiet piece of land, just 5 minutes to downtown Mystic. Enjoy modern comforts and a designers decor, while settling in front of the fire, or taking a short drive to all that Mystic has to offer- hiking, water, shops and restaurants.

Oct 16 – 23

ﺩ.ﺇ825 per night

Guest favorite

Guesthouse in Stonington

4.99 out of 5 average rating, 188 reviews

Super Adorable Cottage + Fire pit + King Bed!

Transport yourself to Mystic's shipbuilding heyday at Smith Cottage. This adorable, open-concept, pet-friendly, two-bedroom retreat in historic Old Mystic captures the essence of a bygone era. Nestled at the head of the Mystic River, it offers a perfect base for exploring the coastline and Mystic Seaport. With Colonial nautical charm and 21st-century comfort, the Smith Cottage invites you to experience genuine New England hospitality. Your journey into Mystic's maritime history begins here!

Jan 7 – 14

ﺩ.ﺇ550 per night

Guest favorite

Guesthouse in Northampton

5.0 out of 5 average rating, 275 reviews

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

Feb 23 – Mar 2

ﺩ.ﺇ453 per night

Guest favorite

Guesthouse in Glastonbury

4.96 out of 5 average rating, 133 reviews

Unique luxurious private building in historic area

Unique private space for sophisticated adult(s). Located just 7 miles from downtown Hartford, 1 mile from Route 2 & 84/91 interchange. Guests may relax in this completely renovated historic Barn, with covered parking, away from street view. Enjoy this luxurious space and the private gym which includes treadmill, eliptical, bike, free weights, boxing bags, and yoga space. Upstairs, walk the catwalk between spacious bedroom and full sized Office / Loft over looking historic Main Street.

Jul 21 – 28

ﺩ.ﺇ503 per night

Guest favorite

Guesthouse in Charlestown

4.88 out of 5 average rating, 269 reviews

Cozy All Season Cabin Near Beach at Rockbriar Farm

Small vintage vacation cabin located in Charlestown, RI a 1 mile walk/bike to the town beach. Located on 7 acres called Rockbriar Farm, the cabin is in a wooded setting away from our home affording privacy for guests. One large room includes the futon bed/couch and the one sink; the shower and toilet are in separate room. Cabin also has a cedar enclosed hot water outdoor shower. Clean, cozy but not luxurious! No stove, but coffee maker, microwave, outside grill, and mini fridge.

Feb 13 – 20

ﺩ.ﺇ362 per night

Guest favorite

Guesthouse in Cranston

4.92 out of 5 average rating, 303 reviews

Waterfront Studio, 10 min to Downtown Providence

Enjoy your own waterfront retreat in this beautifully renovated, professionally cleaned boathouse down a private drive in a quiet, former estate. This hideaway is just 10 minutes to downtown Providence and the colleges and a short, 10-minute picturesque walk to historic Pawtuxet Village for shopping and dining. Enjoy the private deck, full kitchen, king size bed, washer, dryer, and plenty of space for relaxing or working. Note: This space is not suitable for children or infants.

Oct 11 – 18

ﺩ.ﺇ680 per night

Guest favorite

Guesthouse in Killingly

4.97 out of 5 average rating, 119 reviews

The Carriage House at Chaprae Hall

Welcome to the Carriage House at Chaprae Hall! A cozy, quiet respite from a busy world awaits you. This fully furnished & appointed vintage living space has been updated over the years to be an inviting and welcoming stop for your journey. Whether you’re traveling for business, in town for an event, or looking for a central home base for day trips across southern New England, we've got you covered with your own kitchen, full bath, living space, and bedroom with a queen-sized bed.

Sep 10 – 17

ﺩ.ﺇ470 per night

Guest favorite

Guesthouse in Westminster

4.98 out of 5 average rating, 299 reviews

Guest House - 4 miles from Wachusett Mt.

Enjoy your stay in this cozy, newly renovated semi-attached in-law unit. It is located close to Route 2, walking distance to the town center, only 4 miles from Mt. Wachusett in a quiet neighborhood. It has 2 parking spaces and a private entrance. This unique space has everything to make you feel at home – including WiFi and Netflix. The kitchen is equipped with a Keurig Coffee Maker, Mini Fridge, and a Microwave. Queen-size bed, fresh towels, body wash are also provided.

Jan 12 – 19

ﺩ.ﺇ484 per night

Guest favorite

Guesthouse in Hopkinton

4.96 out of 5 average rating, 107 reviews

Cozy Vintage Cottage at Cornerstone Farm

The Cottage at Cornerstone Farm offers a cozy year round get away! This two bedroom vintage style cottage is conveniently located a few miles in from I-95 on a small New England farm. This area of RI and nearby CT offers you so many things to do! Beaches/swimming, golf courses, biking, hiking, kayaking, canoeing, fishing/charter fishing, motor cycling, shopping, fine and/or casual dining (seafood places all around), antiquing, casino's, theater and more!

Oct 3 – 10

ﺩ.ﺇ799 per night

Guest favorite

Guesthouse in Mystic

4.99 out of 5 average rating, 543 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.

Dec 5 – 10

ﺩ.ﺇ688 per night

Guest favorite

Guesthouse in Glastonbury

4.91 out of 5 average rating, 173 reviews

Charming Barn Apartment

Our one bedroom apartment in a colonial barn has a country feeling but is a 10 minute drive into downtown Hartford, and halfway between Boston and New York City .There are woods on one side and from the living area look out on a hillside where you can sit for a spell or spend some time on the private stone patio right outside the door. There are beaches and casinos within an hours drive.

Nov 30 – Dec 7

ﺩ.ﺇ516 per night

Guest favorite

Guesthouse in Granby

4.99 out of 5 average rating, 710 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Mar 1 – 8

ﺩ.ﺇ607 per night