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

A covered outdoor seating area features a combination of woven chairs and a sofa arranged around a stone floor. Soft lighting is provided by string lights overhead, while rustic wooden beams and walls create a warm, inviting backdrop.

Guesthouse in Southbury

4.93 out of 5 average rating, 318 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Top guest favorite

Guesthouse in Bearsville

4.98 out of 5 average rating, 525 reviews

Relax on the Ridge - 2 miles from Woodstock

Stay and relax in a private guest house on a 5+ acre picturesque property overlooking historic Woodstock, N.Y. The cottage is nestled away high on a private road in a quiet country setting, yet conveniently only 2 miles from Woodstock and 10 miles from Phoenicia! Relax on the grounds while watching our Tennessee Mountain, Cashmere & Kiko goats—drive into town to enjoy shops, restaurants, & the unique artistic culture of Woodstock—explore the many beautiful trails that the Catskill Park offers.

Guest favorite

Guesthouse in Easton

4.84 out of 5 average rating, 101 reviews

Entire Guest House at Fox Pond Farm.

Recently renovated private guest house with access to swimming pool offers sleeping for eleven in four bedrooms. Tastefully decorated with all amenities. Close to Merritt Parkway and train to Manhattan. This is a natural refuge on eleven very private acres. Large private terrace faces westerly for amazing sunsets and offers a "Plein Air" environment for alfresco meals, cocktails and relaxation. An attached vegetable and flower garden with fountain offer a quiet space to relax and reflect.

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, 489 reviews

Get Back to Nature at a Modern Wood Clad Getaway

WINTER IS HERE--Glorious winter birds. Come and enjoy a cozy time in our guest house--whether it is a bright sunny day or a beautiful snowy landscape. You can still Hike on the trails. 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 just relax in our cozy guest house. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Guest favorite

A sandy beach scene is featured, showcasing a sleek seal resting on the sand. In the background, a towering rock formation stands under a blue sky filled with fluffy white clouds. The shoreline gently curves toward the water, creating a serene coastal environment.

Guesthouse in Chilmark

4.98 out of 5 average rating, 215 reviews

Beautiful Guest House in Chilmark

This newly renovated guest house is located in a quiet and very private setting in Chilmark. The guest house is located above the garage adjacent to the main house with a private entrance. It has a queen size bed with two oversized chairs. There is a full bathroom in addition to a private outdoor shower. A small kitchen features butcher block countertops, a stainless steel sink, refrigerator and electric stove. Central air conditioning + heat make it the perfect getaway for all seasons.

Top guest favorite

Natural light fills the room through large glass doors, revealing a serene outdoor balcony space with trees and greenery. A decorative table holds candles and a small statue, contributing to a peaceful atmosphere.

Guesthouse in Asbury Park

4.98 out of 5 average rating, 254 reviews

Peaceful Guesthouse

you will have this private, quiet guesthouse all to yourself ..14' ceilings and a 25'x10' balcony to sun on....it comes with 2 free beach passes, and a beach cart with 2 chairs and umbrella......you may have stayed in my front house with the peace sign, now, I am offering my rear guesthouse, originally built in the 1800's as a barn, this redesigned building with 14' ceilings was completely rebuilt in 2003 just 4 blocks from the beach. It is walking distance to everything.

Guest favorite

The exterior of a charming guesthouse is highlighted, showcasing a white facade with large windows and a covered front porch. Surrounding trees provide natural greenery, while the clear blue sky offers a serene backdrop. A swing chair is visible on the porch, inviting relaxation.

Guesthouse in New Marlborough

4.9 out of 5 average rating, 198 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

Guest favorite

Guesthouse in Asbury Park

4.97 out of 5 average rating, 208 reviews

Beachtown house w/ porch, workdesk, outdoor shower

Separate, renovated, sanitized cottage that sleeps 4. 1bd/1ba backhouse with a full bedroom (queen bed) and the living room includes leather sofa bed (queen). Entrance of the cottage has a porch for morning coffee or evening cocktail. Fully equipped kitchen to cook & prepare food for the beach. 42-inch TV & free Wifi. Workspace w/ desk, chair, monitor. Air conditioning/heat throughout the cottage. 2 beach passes, beach towels, beach chairs. Plenty of street parking.

Guest favorite

A bright and airy studio space is presented, featuring a spacious bed centered under a large window. A cozy sofa in front includes colorful cushions, and two black chairs are positioned beside a small table. Natural light enhances the soothing white walls and simple decor.

Guesthouse in Germantown

4.96 out of 5 average rating, 196 reviews

Luxe Guest House Retreat (Sauna)

Welcome to the Guest House nestled in the woods. We designed this lush and light-filled studio with peace and luxury in mind. Situated across from apple orchards, it sits ten minutes from Hudson and ten minutes from Germantown, you get the best of both worlds: country living with two amazing destinations close by. Ideal for a romantic getaway, or to be close to the sights and sounds but can retreat to natural beauty. A true sanctuary from the City.

Superhost

A welcoming bedroom features a spacious bed dressed in soft linens, with a textured throw draping over the side. Natural light filters through sheer curtains at the window, illuminating the hardwood floors and complementing the light-colored walls.

Guesthouse in Saugerties

4.85 out of 5 average rating, 137 reviews

Private Guesthouse in Saugerties

Welcome to the cutest detached Guest House in the village of Saugerties, comfortable walk to restaurants, parks, and HITS. Set on a quiet street with ample street parking . This charming 1 bedroom will surely fit all your needs. Nicely refinished hardwood floors in Living and Bedroom area, also offers Washer/Dryer and storage. Nice sized rooms the bedroom offering a queen bed with big walk- in closet.

Guest favorite

The open living area features wooden floors and beams, with French doors that lead to a stone patio and views of the surrounding greenery. A wooden dining table with four chairs is positioned beside the doors, enhancing the sense of spaciousness and natural light.

Guesthouse in Bearsville, Woodstock

4.95 out of 5 average rating, 435 reviews

Stylish Woodstock Guest House..Mountain View

This 1920's converted barn has the original beams and antique fixtures w/vintage and new furnishings. The french doors on one complete wall amplify the open space with views of the Catskill Mts., pond, fields, and the vast sky. No smoking no pets. You love them, I love them, but they cannot stay here. Also, two night minimum stay. Three night minimum on holiday weekends.

Superhost

The exterior of the guest house is shown, featuring a modern design with dark wooden panels. A stone pathway leads to the entrance. A shaded sitting area with chairs and a picnic table is visible in the grassy landscape, surrounded by trees and greenery.

Guesthouse in Pownal

4.84 out of 5 average rating, 532 reviews

Bauhaus Guest House in So. VT.

Enter through a flowering courtyard into this one room studio style guest house with full bath, closet and sliding glass doors looking out upon a lush green landscape in Southern Vermont. Parking, wi-fi and local insight included. Hosts = AMAZING :) 5 miles to Williamstown Theater Festival, Williamstown, MA 9 miles to Mass MoCA, North Adams, MA 9 miles to Bennington, VT