Vacation rentals in Chesterfield

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.

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.

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.

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.

Cozy Cottage on Spofford Lake

This perfect spot on Spofford Lake will have you coming back every year to make memories without giving up the comfort of home. Plenty of space for everyone inside and out. Comfortably sleeps 4 people. There's so much to enjoy: from a cup of coffee sitting on your porch facing the lake, to swimming, kayaking, enjoying sunsets while making s-mores for the kids at the campfire, grilling burgers with family and friends, and even streaming your favorite shows on a rainy day.

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.

Peaceful cabin close to skiing & Brattleboro

Country privacy close to the best of Southern VT! This spacious home is close to skiing (20 min to Mt. Snow; 35 min to Stratton), river swimming holes, hiking, biking, art galleries and great restaurants. Open concept with fireplace, cook's kitchen, jet bathtub, gardens, winter hot tub off deck, and large patio and fire pit give the perfect vibes for your VT gathering. Secluded from neighbors but close to amenities, this home is a comfortable and peaceful retreat.

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.

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.

Guest House @ 120

Unforgettable designer stay in the heart of downtown Brattleboro. Curated art, luxe finishes, and boutique comfort set this experience apart. Walk to the best cafes, boutiques, and galleries. Enjoy a chef’s kitchen, plush bed, quaint bath, and fast Wi-Fi. Every detail is elevated, every corner styled. Steps from Amtrak, wrapped in Vermont charm. Perfect for escapes, retreats, or inspired work. You won’t want to leave.

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.

Quiet St in Town, gardens, terrace

Private entry, up wide covered stairs to open and enclosed porches, into newly renovated spacious open concept living and kitchen area. Separate large BR with queen-size bed has French doors that open onto the enclosed porch. A few blocks to downtown restaurants, food coop, and shops, walking distance to trails.