Guesthouse vacation rentals in Cheshire County

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 & restoration. A new season, after 10 years of hosting we are selling this property so book while you still can. We have reduced the booking window to the next 30 days only so check in often.

1790 Historic Home in Chesterfield for Five Guests

Our 1800 sq-ft guesthouse is in the historic town of Chesterfield, a mere 5 min from Spofford Lake and 5 min north of Pisgah State Park and Madame Sherri. It is located between Brattleboro and Keene, making both town amenities readily accessible. Built in 1790, when George Washington was President, it is the Original Chesterfield Inn and evokes beauty of a bygone history. The guesthouse has a screened-in porch, where you can enjoy the westerly vistas and the dramatic changes in the seasons.

Peaceful Historic Cottage

Picturesque private two bedroom cottage attached to historic estate, located within the village of Saxtons River. Walking distance to the quaint downtown, Vermont Academy and an extensive network of hiking trails. Short drive to several Southern Vermont attractions including Okemo and the Vermont Country Store. The grounds boast 6 acres of sprawling gardens, an orchard and fire pit perfect for star gazing. Experience this special property which has been owned by the same family for 200 years.

Cottage amongst the trees

Relax in this calm & stylish space. Fully renovated in late 2024, this tiny house sits on 14 acres of land overlooking a seasonal pond, gardens & patios. Hosts live in the main house built in 1803. Great for the travelling professional who is looking for a peaceful & comfortable place to unwind after a long shift at the hospital or day on the slopes. Minutes to downtown Brattleboro yet in a rural setting. Equidistant to exits 3 or 4 on I-91; close to Putney, Bellows Falls, Keene & Mt. Snow.

Monadnock Fall Foliage Large Quiet Studio Sleeps 4

Spacious 550 sq.ft. 2nd flr studio apartment above detached garage with qu. bed, qu.pull out sofa, mini kitchen, and private deck. Perfect for foliage viewing, skiing, and summer adventures. Short drive to great restaurants, artistic venues, antiques, and all that New England has to offer. Walk to village of Hancock, Norway Pond, Fiddleheads Cafe, and the Hancock Market. Between Keene and Concord, 10 min to Peterborough. Military discount available, please message us for details.

Newly Renovated Guesthouse

Welcome to your private retreat! Nestled on a serene acre of woodland, this newly renovated guesthouse offers a calming escape with modern amenities and peaceful surroundings. Perfectly situated just 5 minutes from the heart of Putney (and I-91), you’ll enjoy easy access to local attractions, including the Putney Co-op, Next Stage Arts, and a nearby swimming hole. Outdoor enthusiasts will love being close to scenic woods and trails, ideal for hiking and reconnecting with nature.

Romantic Mountain View Guest Cabin

Escape to our romantic cabin, nestled in the Monadnock region of New Hampshire. This contemporary retreat was designed with a private screened in porch and large front deck perfect for grilling and taking in the stunning mountain views. A short walk or drive to several lakes and ponds, hiking trails, and quaint New England towns, our cabin is the ideal place for a quiet and beautiful romantic getaway. Book your stay and experience the natural beauty of this New Hampshire gem..

Lakeside Couple's Getaway

If you are seeking a fun couples getaway at a stunning lakeside retreat, then look no further. The natural and rustic charm of a crystal clear lake in the woodlands of New Hampshire offer you a chance to unwind and relax. Summertime offers swimming, kayaking, paddle boarding and much more! Your stay includes access to 1 double kayak and 2 paddle boards. Located just 10 miles outside of the charming historic town of Keene where you can find many great restaurants and shops!

Cozy private studio -full kitchen and bath

Welcome to our private studio apartment in Walpole New Hampshire! The perfect blend of comfort and convenience! Prepare breakfast with fresh eggs from our coup and unwind in the hot tub. This fully furnished space has a private entrance, own driveway and located five minutes from the town of Walpole where you’ll find coffee shop, restaurants, grocery store and more. Whether you’re here for a short stay or an extended our space offers the comfort you need!

Field and Mountain House

Visit this beautifully peaceful, newly built guest house, with its spectacularly intimate view of Mount Monadnock! Ten acres of open fields and complete visual privacy from main house. Artful, tasteful interior. Fantastic small towns and great restaurants dot the region. Larger Peterborough and Keene are just a 20 min drive. Perfect for outdoors people, writers, artists. Abundant hiking, lakes, music, and art all about. (Longer term stays welcome, too.)

Copley’s Guest House on Lake Monomonac

A very unique, beautifully designed Belgium Farmhouse Guesthouse located above a garage on Lake Monomonac. You will have your own access to kayaks and a paddle board to enjoy everything the lake has to offer. All seasons can be thoroughly enjoyed here; boating, fishing, swimming and other water sports in the summer, vibrant colors and crisp air of fall, in the winter enjoy iceskating and fishing, then end the day with a good book by the fireplace.

Bucolic New Hampshire Farm Cottage at Mayfair Farm

Want a relaxing, country getaway? Mayfair Cottage is the perfect place for nature lovers, whether you want a quiet retreat, family vacation, or romantic escape. Visit the farm animals, shop for local goods in our farm store, unwind, and watch the sunset over Mt. Monadnock. Mayfair Farm is nestled in the hills of Southern New Hampshire, five minutes from the historic village of Harrisville and less than two hours north of Boston.