Vacation rentals in Chesterfield

4.91 out of 5 average rating, 112 reviews

Two white lawn chairs are positioned around a stone fire pit in a wooded area. The ground is covered with gravel and scattered leaves, while smoke rises gently from the fire. Tall trees surround the space, adding to the serene environment.

Home in Chesterfield

Governer's Brook Camp - 2 Bedroom

Renovated camp, 800 sq ft, betweeen Brattleboro VT & Lake Spofford NH. Hiking trails start at the backyard. It’s 15 minutes to Brattleboro, 5 minutes to the boat ramp on the Connecticut River, 15 minutes to Lake Spofford, and 50 minutes to Mt. Snow. Across the road is a (seasonal) tumbling waterfall and gorge called “the Devils Den”. The backyard leads to woodlands with miles of trails. Enjoy a relaxing evening by the firepit overlooking the brook. Or outdoor cooking on a propane grill.

Guesthouse in Brattleboro

An outdoor gathering area is surrounded by lush greenery, featuring a wooden fire pit and four seating options. Two curved wooden chairs and two bench-style seats are arranged around the fire pit, creating a cozy atmosphere for relaxation in nature.

4.92 out of 5 average rating, 528 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.

4.82 out of 5 average rating, 271 reviews

A bathtub is positioned beside a large window, offering views of the surrounding greenery. Natural light filters through sheer curtains, illuminating the tub and a neatly rolled towel placed nearby.

Cottage in Putney

The Cottage, a house built for guests.

In the village there is a wonderful farm to table restaurant, the Gleanery. A local pub, friendly, great food with indoor and outdoor dining & pub. The General Store, is the oldest continually run general store in Vt. The Next Stage, Yellow Barn, Sandglass Theater, these places provide an amazing collection of visual, musical, spoken word and world renowned art and artist to experience. These cultural event locations are but a mile away for the Cottage I hope you choose for your stay.

4.88 out of 5 average rating, 161 reviews

The compact kitchen features modern appliances, including a microwave and refrigerator, paired with wooden cabinetry and a dining area. Light-colored wood flooring extends throughout, and a staircase leads to the sleeping loft above. Decor elements include framed artwork and a vase of flowers positioned on the counter.

Tiny home in Brattleboro

Sweet Vermont Tiny Home Get Away

Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

4.99 out of 5 average rating, 139 reviews

A modern kitchen features dark cabinetry and a sleek countertop. Above the sink, a window graphic displays a vibrant landscape of fields and sunlight. An under-mounted sink and essential appliances are visible, along with subtle decorative touches like a vase of flowers.

Apartment in Brattleboro

River View apartment

Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by A gorgeous view of the river and mountain across the street .

4.93 out of 5 average rating, 139 reviews

A night sky displays a gradient of purple and dark blue tones, with stars scattered across the expanse. Silhouettes of power lines extend from the foreground into the distance, contrasting against the celestial backdrop.

Camper/RV in Guilford

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for up to two adults and one kid (63" long fold down couch).

4.94 out of 5 average rating, 1,269 reviews

A snow-covered mountain is visible in the distance, with skiing trails marked by white lines. Soft clouds drift across the peak, bathed in the warm colors of sunset. Surrounding trees are silhouetted in front of the mountain, adding depth to the natural landscape.

Tiny home in Jamaica

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Guest suite in Brattleboro

The entrance of the building is illuminated by two wall-mounted lanterns, casting a soft glow. The large double doors are a dark shade, while colorful stained glass can be seen through the arched windows on either side, highlighting the architectural details.

4.94 out of 5 average rating, 586 reviews

Charming studio in renovated 19th century church.

This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

4.93 out of 5 average rating, 353 reviews

A light yellow exterior of a two-story building is visible, featuring a sloped roof and a garage door on the left. A manicured garden with shrubs and decorative elements is positioned near the entrance, along with a satellite dish mounted on the wall.

Condo in Brattleboro

Private & Quiet Studio Apt. in Vermont

Clean, comfortable , quiet and snug, this studio apartment is a great place to come and relax in. It has a comfy QUEEN size bed with a 40” LCD at its foot, a kitchen set up for cooking and a desk with a view of a green field. This apartment is situated on the ground floor of our detached garage. Our garage sits behind our home, well away from the street. We live in a residential neighborhood that is conveniently located near I91, Route 30, Route 9 and Downtown .

4.95 out of 5 average rating, 176 reviews

Apartment in Brattleboro

Contemporary forest eco-retreat, mountain views

This is an open, light-filled one-Bdm apartment on the lower level of our hillside home, surrounded by forests, with stunning views. Your space is 719 sf + access to laundry. We are fully vaccinated, and ask the same of guests. If you think you may have Covid please tell us. We welcome all kinds of people, regardless of race, ethnicity, gender, etc. We may ask questions before accepting people who don’t have many prior reviews. We don't take pets, sorry.

4.98 out of 5 average rating, 420 reviews

A wooden deck surrounds a charming cottage, featuring large windows and a welcoming entrance. Potted plants are thoughtfully placed, complementing a rustic table and chairs. The exterior combines natural wood finishes, blending harmoniously with the lush green backdrop of trees.

Cabin in Putney

Vermont Retreat Cottage |Exquisite Romantic Escape

A romantic and private getaway on a peaceful six-acre farm with views of fields and forest. ☽ Featured in STAY; Gorgeous Cabins of the East Coast ☽ Elevateddesign; thoughtful lighting; deeply romantic ☽ Quiet & private; star-studded skies ☽ Woodstove, deck, reading nook, firepit ☽ Local's Area Guide with our favorite spots ☽ Strong wifi, no TV ☽ Scrupulously clean using unscented products

4.98 out of 5 average rating, 264 reviews

A circular stone fire pit is surrounded by four brown Adirondack chairs on a grassy area, offering a relaxed space for gathering. The backdrop features a forest of green trees, enhancing the natural setting.

Home in Chesterfield

Charming Country Home

Charming one level ranch style home. Quiet country neighborhood 5 miles from Keene, NH, 10 miles from Brattleboro, VT. The home has a fully equipped kitchen, smart TVs, spacious rooms, two bedrooms, two full baths, laundry in basement, couple of steps to master bedroom. Great backyard. Spacious driveway with motion lights.

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Other great vacation rentals in Chesterfield

5 out of 5 average rating, 13 reviews

Cabin in Dummerston

Peaceful A-Frame in VT | Sauna, River, Cozy Porch

JakeRating, 5 stars2 weeks ago

Great place to stay if you’re looking for a peaceful retreat into the woods. This is a quaint, quiet retreat that provided us a relaxing getaway from the city. The property is surrounded by lush greenery and a beautiful stream. Inside, the projector makes for awesome movie nights. The kitchen provided everything one would need. The bedroom is good, but be mindful of a large step up to get into bed. This place isn’t for the faint of heart if bugs aren’t your thing. Came across a bit, but friendly spider and our dog picked up a couple of ticks. Nothing the hosts can do and they provided tick spray. The hosts are super responsive, helpful, and accommodating. You can’t ask for a better host honestly. Great place, highly recommend!

4.87 out of 5 average rating, 45 reviews

A welcoming porch area features a light-colored sofa and small tables. Greenery surrounds the space, with vibrant yellow flowers adding a touch of color. The entrance is framed by wooden railings, leading into the cozy interior visible through large sliding doors.

Cabin in Dummerston

Coverd Bridge Cabin

JelaniRating, 5 stars2 weeks ago

This was everything we asked for and more! Beautiful cabin with amazing views, privacy and amenities inside and out. A lovely hiking trail with access right in your backyard, a stream as well and plenty of seating. Everything you would need and imagine for a weekend getaway just to enjoy the peace and tranquility to connect with nature is right here. Couldn’t ask for a better experience.

4.97 out of 5 average rating, 97 reviews

An outdoor space features a fire pit surrounded by log seating, with flames crackling in the center. In the background, a deck with steps is visible, above neatly stacked firewood. Bistro seating is arranged on gravel, complemented by greenery and nearby structures.

Apartment in Putney

Minimal organic hideaway inspired by nature

ItaRating, 5 stars2 weeks ago

Katherine’s space was so cozy! It was exactly what I needed for a retreat from daily life. I found both the loft and the daybed very comfortable. There were dimmers on most of the light fixtures, which was important to me because I like low-light settings. The kitchen included a counter with stools and was really quite beautiful. This Airbnb was within walking distance to a local restaurant, the general store and a food co-op. I decided not to rent a car because I was there for R&R., however , if you had a car, just a few minutes outside of town you would see beautiful trees all with leaves in there spring splendor. You could get to Brattleboro in about 20 minutes if you’re looking for more choices of restaurants.. (I decided to take the train up so I took a taxi to the Airbnb from the train and back to the train at the end of my trip.). Although it rained most of the time I was there, it was perfect for my goal of R&R.

4.94 out of 5 average rating, 17 reviews

A warm wood-paneled interior features a cozy seating area with a bench and a rocking chair. Large windows provide views of the surrounding forest, while a patterned area rug and a vintage lamp add to the rustic charm.

Cabin in Brookline

Off-the-Grid Cabin in the Forest

AndrewRating, 5 stars2 weeks ago

Ideal cabin in the woods for a secluded forest getaway - well stocked kitchen, and the outhouse is 10/10. Very responsive and helpful!

Place to stay in Chesterfield

A lighted pergola is surrounded by a stone patio, featuring a circular fire pit at the center. Six wooden Adirondack chairs are arranged around the fire pit, complemented by a rustic wooden railing that encloses the space. Lush greenery is visible beyond the structure.

5 out of 5 average rating, 49 reviews

The Ultimate Romantic Getaway

StephanieRating, 5 stars8 months ago

The hosts were so friendly and the place is truly beautiful. The “glamping” tent was spacious, super comfortable, and had all the amenities. It allowed us to enjoy the beauty & peace of the outdoors with all of the typical comforts of being indoors. The surrounding wood pergolas / porch / patios each had their own unique features to enjoy during different parts of the day! Wonderful and romantic getaway!

Cabin in West Brattleboro

4.94 out of 5 average rating, 17 reviews

Hidden Forest Cabin: Kitchen, Deck, Babbling Brook

AmyRating, 5 stars2 weeks ago

The house is wonderful - beautiful setting, clean and comfy. Everything you need to enjoy a get away. A short drive to Brattleboro which has plenty of restaurants and stores to enjoy. Theresa and Megan were great hosts. They were very responsive and provided easy to follow instructions plus recommendations of places to eat and explore. Our highlight was breakfast on the deck looking out onto the brook. A very peaceful and beautiful setting. We hope to return.

4.94 out of 5 average rating, 48 reviews

A cozy table is set near floor-to-ceiling windows, featuring three birch-inspired candles and a book. Sunlight floods in, illuminating the forest view outside, where trees and a grassy area create a serene atmosphere.

Home in Guilford

Vermont Mirror House

GeorgeRating, 5 stars3 days ago

I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.