Vacation rentals in Chesterfield

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Value · Family · Layout

Forest Street Retreat Attached Guest House

Less than 1 mile from the Retreat Farm, this private & peaceful attached carriage house is perfectly located in the heart of Brattleboro. Only steps from the Retreat Woods nature trails & a short walk into historic downtown, you'll find coffee shops, bookstores & the Stone Church nearby. Thoughtfully designed to have a minimal cozy cabin feel, the downstairs is open concept living w/ a gas fireplace. Both bedrooms are upstairs. Outdoors, enjoy 10 miles of trails & the beautiful West River.

Location · Family · Quiet

Cozy Downtown Getaway!

Welcome to our charming Airbnb nestled near downtown Keene, New Hampshire! Our property offers a cozy and welcoming retreat for guests looking to experience the vibrant culture of this historic city. With its convenient location, you'll find yourself just a short stroll away from the bustling shops, eateries, and attractions that downtown Keene has to offer. The spacious Airbnb boasts 3 bedrooms, 2 bathrooms and ample living spaces making it ideal for families or groups of friends traveling.

Location · Family · Check-in

Governer's Brook Camp - 2 Bedroom

Renovated camp, 800 sq ft, near Brattleboro VT & Lake Spofford NH. Hiking trails start at the backyard. I15 minutes to Brattleboro, 5 minutes to the boat ramp on 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. ...2 Kayaks.

Value · Location · Laundry

Cozy Home for 2-5 People in Vermont

Comfortable house for 2 to 4 people (two queen-sized beds) and a pull-out couch for a 5th person and a self-inflatable bed. Located in a quiet neighborhood. There are two main bedrooms with queen beds in each. There is also a pull-out couch in the room with the fireplace though it is not as comfortable as the self-inflatable bed (and deflatable) in the house. Fast Wi-Fi from Xfinity. Easy to get into Brattleboro Center and an excellent location for exploring Southern Vermont.

Family · Value · Solo travel

Peaceful and Private Farmhouse Retreat

Welcome to a peaceful New England farmhouse getaway, set among over 300 acres of conserved land, including wooded and meadow trails, just outside Chesterfield, New Hampshire. This spacious three-bedroom, two-bath farmhouse offers a rare blend of comfort, beauty, and quiet. Large windows throughout the home frame sweeping views of scenic fields and countryside, creating a light-filled, calming space that is perfect for families, couples, and small groups seeking a restorative stay.

Family · Condition · Amenities

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Discover the ultimate outdoor experience in Southern NH! Enjoy a year-round private hot tub in a covered gazebo, fire pit, hammock, life-size games, and swing set. Located in one of Keene’s safest, quietest neighborhoods, walking distance to downtown and across from Keene Ice Rink. Close to beaches, hiking, and ski resorts. Features a fully stocked chef’s kitchen, wine cooler, and luxury Purple mattresses with individual mini-splits in each bedroom for optimal comfort.

Location · Family · Heating

Lakehouse Getaway

Beautiful cottage on New Hampshire's gorgeous Spofford lake. Perfect for relaxing, swimming, and recreational activities. Hike at local state parks and on Mount Monadnock or walk around, shop and, dine in the beautiful cities of Keene, NH and Brattleboro, VT, only a ten minute drive in either direction. The cottage has a deck to eat breakfast, lunch, and dinner while overlooking the lake, a grill, dock and platforms to relax and read or soak in the sun.

Location · Family · Indoor spaces

Peaceful Beautiful Mountain Home Spectacular Views

15 Spectacular Acres! Plenty of room for the entire family or great for a couples getaway. This home has everything you need. There are brand new mattresses, quilts, linens, towels, cookware, plates and utensils for your comfort. The beautiful mountain views are seen from just about every room. There is a wood burning fireplace, 4 bedrooms and 2 full bathrooms. Both levels have 3 season porches to enjoy the views, coffee, reading or a meal.

Family · Location · Indoor spaces

Spacious Brattleboro home on river, walk to town

Spacious 3,000 sq. ft. home with 4 bedrooms (3 queens, 2 twins) and 4 bathrooms, 3 en-suite. Enjoy a formal living room with grand and upright pianos, a cozy TV room, and a fully equipped kitchen with eat-in area leading to a deck with stunning river and mountain views. Formal dining seats 12. Expansive grounds are perfect for relaxing or hosting special events. Just a 10-min walk to Brattleboro’s Main Street shops, cafes, and culture.

Value · Family · Skiing

Apt in town 2 BR/2 levels in Victorian Farmhouse

We're two blocks from Main Street and it's just a few blocks more to the local theater, art and culture, a variety of excellent restaurants, and walking trails. You’ll love my place because we're so close to town, but not on a main through street, so it's quiet here. My place is good for couples, or a group of friends, solo adventurers, traveling professionals, and for a great get-away.

Location · Value · Hospitality

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.

Family · Location · Quiet