Guesthouse vacation rentals in Connecticut River

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Connecticut River

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

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Guest favorite

Guesthouse in Northampton

5 out of 5 average rating, 321 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!

Guest favorite

Guesthouse in Woodstock

4.98 out of 5 average rating, 233 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED. ZERO CONTACT WITH OWNERS.

Guest favorite

Guesthouse in Corinth

5 out of 5 average rating, 138 reviews

The Guest House at Chandlery Farm

This classic Vermont farm estate has everything that description implies: end-of-the-road privacy with breathtaking views, where the only sound is the wind rustling through the leaves. The manicured gardens, stone walls and quaint but luxurious home seem plucked from classic American folklore. Guests can drink their morning coffee while soaking in views of rolling pastures and forested hills, and spend their days exploring the property's trails, and the beautiful towns and countryside nearby.

Guest favorite

Guesthouse in Brattleboro

4.98 out of 5 average rating, 219 reviews

Light Filled Loft in the Vermont Countryside

Our spacious, tranquil, light-filled Barn Loft is thoughtfully and creatively designed. Complete with a living area, sleeping alcove, flat-screen TV, full kitchen, dining area, and large bathroom with a deluxe shower. A private deck with seating that looks out into our lovely Vermont woods and verdant gardens is attached to the loft. Stay a night or a week, there is plenty to do in every season. We are a friendly, welcoming, worldly, family. We look forward to hosting you at our country home.

Guest favorite

Guesthouse in Wilton

4.95 out of 5 average rating, 622 reviews

Cottage beside a waterfall

Our 1840’s renovated grist mill is located in the beautiful Monadnock Region. The house and cottage are situated on twelve acres and includes gardens, an orchard, berry bushes, grape vines, beehives, a dog, and a tremendous waterfall. We are close to many of nature’s gems including Mount Monadnock, Pack Monadnock, the Heald Tract hiking trails, skiing, snowshoeing and swimming. Also the acclaimed MacDowell Arts Center, Andy’s Summer Playhouse, Andres Institute of Art and the Waldorf Schools.

Guest favorite

Guesthouse in Brattleboro

4.92 out of 5 average rating, 489 reviews

Mahalo Temple Retreat

Retreat in Mahalo's beautiful, private sound healing temple surrounded by nature, amongst streams, berry bushes, fruit & nut trees, medicinal plants and veggie gardens. We are set back just enough from a main road to find your serenity and yet close enough to civilization for human interaction and trails for hiking. Quiet and peaceful location just a few min off I-91 and just over 2 miles from the center of Brattleboro. A fun and quirky town with art cafes, restaurants, and great shops.

Guest favorite

Guesthouse in Cranston

4.92 out of 5 average rating, 349 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.

Guest favorite

Guesthouse in New Ipswich

4.95 out of 5 average rating, 332 reviews

"The Porch" Your cozy home away from home!

Welcome to The Porch! Ready for a mini vacation, or just a place to hang out, or work from? You are most welcome here! . This cozy cabin is very flexible and user friendly! It is private to only your group! The downstairs with all it offers, is for one or two person stays. The upstairs becomes available if you enter 3 or more people. This building is in the backyard of our home, as in photos on our Airbnb site, Other info is listed there also! Info book is in room! Welcome!

Guest favorite

Guesthouse in Highgate

4.97 out of 5 average rating, 606 reviews

Beautiful lake-front cottage, Lake Champlain

Lakefront cottage located in Highgate Springs, Vermont, on the Canadian border. The 2-bedroom cottage sits adjacent to the owner-occupied main house, on a large one-acre lot, with 120 feet of Lake Champlain shoreline. Enjoy the stunning sunset views while sitting on the deck overlooking the water. Private dock included. Montreal and Burlington each 45 minutes away. Available level-2 car charger. Well-behaved pets allowed. Super-fast WIFI!

Guest favorite

Guesthouse in Mystic

4.98 out of 5 average rating, 599 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.

Guest favorite

Guesthouse in Amherst

4.95 out of 5 average rating, 547 reviews

Cozy get-away!

This quiet option is less than two miles from the center of downtown Amherst, a thriving college town with museums, libraries, small stores, restaurants for every budget, hiking trails galore. We offer a relaxing space in a friendly, safe, residential neighborhood. Five minute walk to 2 bus stops. If you are looking for some privacy with access to western Mass., you've found it!

Guest favorite

Guesthouse in Putney

4.97 out of 5 average rating, 270 reviews

Cozy cottage loft and retreat

Returning guests, please ask about our discount! Relax and recharge in our peaceful Vermont cottage. Enjoy this sweet getaway with hardwood floors, fast wifi, a fully equipped kitchen, a quiet sleeping loft with a queen size bed, gorgeous natural light, views of surrounding hills and pond, gardens, and your own private entrance and back deck next to the Putney Brook.