Guesthouse vacation rentals in Pioneer Valley

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Pioneer Valley

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

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Top guest favorite

Guesthouse in Marlboro Township

4.97 out of 5 average rating, 160 reviews

Refined, serene and like no other, Marlboro, VT.

Our elegant, supremely comfortable, and private guesthouse is surrounded by a wonderful garden and 350 acres of woodland in the quiet of rural Vermont. We are 30 minutes from Brattleboro to the east, with its many shops and restaurants, and 12 minutes from the small town of Wilmington to our west, with some restaurants, shops, and a supermarket However, we always recommend bringing groceries, etc., for your first night and next morning. We are pleased to offer a 20% discount for 7 days or more!

Guest favorite

Guesthouse in Pownal

4.95 out of 5 average rating, 181 reviews

"The Library Suite"

This beautiful and spacious property is located at the former Inn at Oak Hill and Cherry Court. It's convenient to Williams College, Williamstown Theatre Festival, Clark Art Museum, MassMOCA, Fresh Grass Festival, Jiminy Peak, Bennington College, and many other destinations in southern Vermont and western Massachusetts. Comfortably furnished with modern amenities such as Wi-Fi and satellite TV, this innovative space also surrounds you with beautifully preserved and rustic architectural features.

Top guest favorite

Guesthouse in Shelburne Falls

5 out of 5 average rating, 268 reviews

Shelburne Guest House -The Ranch

The nice thing about my home in Shelburne is the location & the peace & quiet. 10 minute drive to Greenfield Rotary I-91, easy drive to Amherst, Smith, UMass, NMH, Deerfield Academy & Stoneleigh Burnham School. Berkshire East nearby for outdoor sports. 5 minute drive to the Village of Shelburne Falls, hiking trails, bike paths, High Ledges, & the Bridge of Flowers. Updated 1964 Sears Roebuck catalog home. Bright & sunny! Large farmhouse kitchen, 3 cozy bedrooms. Large yard! Your Vacation Home!

Top guest favorite

Guesthouse in Northampton

5 out of 5 average rating, 346 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!

Top guest favorite

Guesthouse in North Adams

5 out of 5 average rating, 263 reviews

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

Guest favorite

Guesthouse in Vernon

4.92 out of 5 average rating, 109 reviews

Cozy private one bedroom guest apt suite

Centrally located, just minutes from I84, 20 min to Uconn, 15 min to capital of Hartford, 1 hour drive to Cts famous casinos, 30 min to MGM Springfield, enjoy local dining close by. Private entrance guest suite with parking for one vehicle at your door. Private bedroom with double bed and pull out sofa in living room area, workspace, smart tv, internet ready, kitchenette with fridge, microwave, 2 burner cooktop, and coffee maker, snacks and refreshments, linens, some toiletries available

Superhost

Guesthouse in Brattleboro

4.91 out of 5 average rating, 516 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 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 Fitzwilliam

4.86 out of 5 average rating, 361 reviews

Detox Healing Sanctuary with Wood-Fired Sauna

Escape the city & take a break from hectic schedules & life's demands. We invite you to embrace life at a relaxed pace surrounded by nature on our 1810 farm. Enjoy the fire pit, walk the trails, forage for treasures & unwind in the wood fired sauna! Rest and reset your life & cultivate space for stillness & healing We've created a place for you to unwind & restore your soul, & detox & recharge your body. For the full retreat ask about day pass to Covey House Spa

Guest favorite

Guesthouse in Stockbridge

4.91 out of 5 average rating, 127 reviews

Modern barn in the heart of the Berkshires

Modern, renovated, historic dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature.

Top guest favorite

Guesthouse in Granby

4.99 out of 5 average rating, 813 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!

Top guest favorite

Guesthouse in Amherst

4.96 out of 5 average rating, 584 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!

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What guests are saying

The Robert Frost Trail Lodge

4.83 out of 5 average rating, 6 reviews3 weeks ago

Our stay at Cheikh’s was perfect for my husband, daughter, and I while visiting UMass. Cheikh was very friendly. His property was beautifully decorated and immaculate. It had a relaxing, serene, woodsy vibe. We could not have been happier with our stay! Thank you, Cheikh.

Guesthouse in Amherst

What guests are saying

Fern Valley Frame

4.99 out of 5 average rating, 70 reviews5 months ago

This was the perfect escape! I came out for a solo getaway and everything was so beautiful and peaceful. The cabin was cozy and well stocked with anything you need. Even in the November cold the outdoor bathroom and grill were easy to use, and the hosts were kind enough to provide extra water bottles since the outdoor hose was frozen. Inside was warm and so comfortable. Sarah was so communicative and sweet, finding the place and checking in/out was a breeze. My only regret was not booking an extra night - I didn’t want to leave! I can’t wait to come back.

Guesthouse in New Braintree

What guests are saying

The Granary at House on Golden Hill

4.93 out of 5 average rating, 365 reviews1 week ago

The Granary was a truly lovely place to stay. From the moment we arrived, it felt warm and inviting, and we really appreciated how uncluttered and spacious it was. The bed was exceptionally comfortable – we slept so well! My only suggestion for improvement would be the addition of light-blocking blinds in the bedroom, as the early sunrises did make it a little difficult for me to sleep in. However, this was a minor point in an otherwise fantastic experience. The gas stove and well-equipped kitchen made cooking dinner a breeze, and the location was absolutely perfect. We loved having such easy access to beautiful trails and hiking spots, and the charming restaurants in Lenox were just a short drive away. For anyone planning to visit Tanglewood or Kripalu, The Granary would be an ideal base. We also enjoyed having the pull-out sofa for a cozy movie night in, and the skylight in the living room added a wonderful touch, especially in the evenings. We definitely recommend!

Guesthouse in Lenox

What guests are saying

Modern studio with views of the treetops

4.96 out of 5 average rating, 227 reviews1 week ago

This is a lovely studio with views of the treetops, as described! We love the location and the studio is very clean, making it a very peaceful and relaxing environment. A great spot for a getaway! Chelsea was very responsive. All the home instructions are clear and easy and the location guide on Airbnb was very helpful if you want to shop and/or stroll the nearby outdoors.

Guesthouse in Stockbridge

What guests are saying

Casita by the Green: Quiet, Country, close to town

4.93 out of 5 average rating, 70 reviews2 months ago

We had a fantastic stay at Cyndi’s place! She is an incredibly helpful and thoughtful host, going above and beyond to make sure we were comfortable. She even provided us with milk and cream, which was such a kind touch. The accommodation was clean, cozy, and well-equipped, making our stay even more enjoyable. Highly recommend staying here if you’re looking for a welcoming and hassle-free experience!

Guesthouse in Brattleboro

What guests are saying

Adorable 1 bedroom guesthouse in country setting.

4.73 out of 5 average rating, 37 reviews6 months ago

We were last minute guests and Michael and Jennifer were so gracious to let us stay. The mountain air and the occasional passing train made an idealic atmosphere. The cabin is surprisingly large and had everything we needed. Others have noted a wifi or cell service concern but that was not our experience. Thoroughly enjoyed our stay.

Guesthouse in Florida

What guests are saying

A Barn Experience

4.95 out of 5 average rating, 76 reviews3 weeks ago

I can’t say enough nice things about Jean and this beautiful property. I stayed a month and felt right at home. Jean was friendly and responsive and anxious to ensure I had a comfortable stay. This property was inviting and had every amenity I needed. I hope to come back!!

Guesthouse in Stafford

What guests are saying

Tiny Home in a Huge Lot!

4.63 out of 5 average rating, 8 reviews17 months ago

From the reservation, through the stay, including check-out, Celeste's directions and communication was thorough and helpful. An earlier review mentioned the sofa bed could have been more comfortable. For my stay, there was a single bed with separate sofa, both of which were quite comfortable. Thanks for a great stay.

Guesthouse in Granby