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 Hartland

4.96 out of 5 average rating, 160 reviews

Cottage for Two/Solo Getaway/Musician's Retreat

Luxurious, well appointed cottage with beautiful sunrise view located between Woodstock VT and Hanover NH. An inspiring treat for musician’s getaway is a fully restored 1929 Steinway L. Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer and very comfortable queen bed. A romantic getaway in the woods, a place to relax, work in peace, or explore the beauty and history of the area. Hiking, biking, fly fishing, hot air balloon rides and shopping are all close by.

Dec 6 – 13

G$32,926 GYD 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

G$25,210 GYD per night

Guest favorite

Guesthouse in Woodstock

4.98 out of 5 average rating, 209 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.

Jan 5 – 12

G$32,782 GYD per night

Guest favorite

Guesthouse in Wilton

4.95 out of 5 average rating, 573 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.

Sep 20 – 27

G$31,552 GYD per night

Guest favorite

Guesthouse in Springfield

4.86 out of 5 average rating, 322 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

Nov 18 – 25

G$19,049 GYD per night

Guest favorite

Guesthouse in Belmont

4.99 out of 5 average rating, 201 reviews

Charming Pool/Garden Guest House

A little Paradise! Charming pool and guesthouse in country setting, birds and flowers galore. Much to do in the area, or just quiet, settling into some refresh-your-soul time. The guesthouse has all you need to feel at home. Within 15 minutes you'll find Gunstock Recreational Area, Highlands Mtn. Bike Park, Hermit Woods Winery, Funspot bowling and arcades, hiking, fishing, Shaker Village, Lakes Region Casino, NH Speedway, Bank of America Pavillion (concerts) and Tanger Outlet Shopping.

Sep 18 – 25

G$27,790 GYD per night

Guest favorite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 433 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.

Jul 9 – 16

G$21,952 GYD per night

Guest favorite

Guesthouse in New Ipswich

4.94 out of 5 average rating, 300 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 at, 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 rentals. 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!

Nov 21 – 28

G$17,667 GYD 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

G$26,928 GYD 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

G$33,755 GYD per night

Guest favorite

Guesthouse in Groton

4.98 out of 5 average rating, 246 reviews

Groton Forest Retreat

Comfortable, secluded, sparkling clean 2nd story loft IN Groton State Forest, and offering privacy, peace, and quiet. Forest trails outside your door; star-gaze with little to no light pollution! Hike, byo bike, swim, byo kayak, explore; foliage in Fall. To ensure the safety of all guests, A&K are fully COVID-19 vaccinated and ask all guests to be fully vaccinated as well.

Jan 11 – 18

G$24,327 GYD per night

Guest favorite

Guesthouse in Loudon, New Hampshire, US

4.97 out of 5 average rating, 239 reviews

Pastoral Farm in NH

Cozy private get away. A little bigger than a tiny house, apart from the main farm house and barns on a beautiful hill top setting. Sit and relax , take a walk through the fields or if your feeling a little more adventurous explore the beaver pond or hike out to picnic rock. This is country living in NH. *Please note that we are 8/10ths of a mile out on a dirt road.

Mar 22 – 29

G$24,444 GYD per night