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, 164 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, 141 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, 141 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).

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.

4.92 out of 5 average rating, 201 reviews

A view of a downtown street scene featuring two distinct brick buildings. On the left, New England Sweetwater Farm & Distillery displays large windows and a sign announcing the tasting room. The adjacent structure, a modern three-story building, showcases a balcony above the street.

Apartment in Winchester

Downtown Loft next to Distillery

Enjoy a lovely weekend getaway in this cute 1 bedroom loft, centrally located in Winchester, NH. Enjoy a tasting at New England Sweetwater Farm & Distillery next door. This cozy loft features a full kitchen, 3/4 bath as well as a bedroom and living/dining room. 20 minutes to Keene, Brattleboro and Chesterfield. Access to Pisgah State Park, the Ahsuelot Rail Trail and Forest Lake. Come see what our beautiful area has to offer!

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.

4.98 out of 5 average rating, 320 reviews

A hammock is suspended between two trees in a grassy area, surrounded by lush greenery. Sunlight filters through the leaves, creating a serene atmosphere. A stack of firewood is visible nearby, adding to the natural setting.

Guesthouse in Putney

Cozy cottage loft and retreat

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.

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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, 46 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.

4.96 out of 5 average rating, 71 reviews

The cottage exterior features a wooden facade with a green metal roof, framed by vibrant trees. A covered porch with potted flowers welcomes visitors, while large windows allow natural light to fill the space. The peaceful setting highlights the connection to nature.

Cabin in Guilford

Guilford Grove Cottage

ElizabethRating, 5 stars6 days ago

We truly loved staying in this beautiful, cozy cabin. It was just the right size for the two of us, and very comfortable. The view of trees and wildflowers was lovely and refreshing. It was also fun to have a couple of cats walk across the porch each day! Joel was very proactive and friendly, which we greatly appreciated.

Guesthouse in Brattleboro

A private deck is shown with a dining table set for four, surrounded by comfortable chairs. Potted flowers add a touch of nature. Nearby, a single green chair rests against the house, creating a cozy outdoor space overlooking the calming landscape.

4.93 out of 5 average rating, 70 reviews

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

GuangliangRating, 5 stars3 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!

4.85 out of 5 average rating, 27 reviews

A spacious deck features a cozy seating arrangement including four metal chairs and a dining table, surrounded by a wooden railing. A patterned outdoor rug adds texture to the area, with lush greenery visible in the background under a bright blue sky.

Cabin in Winchester

The Ironclad Mountain Retreat

JenniferRating, 5 stars3 weeks ago

Could not have asked for a more perfect and peaceful stay at the mountain house. It is a dream of a place, in beautiful surroundings.

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!

4.92 out of 5 average rating, 49 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 stars1 week 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.