Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

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Guest favourite

Cabin in Chesterfield

4.91 out of 5 average rating, 116 reviews

The Glow Room at Indian Hollow

The Glow Room at Indian Hollow is a history-rich 1850 post & beam barn, renovated in a light-filled, post modern style. Imagine getting out of your car, opening the screen door to a big porch that overlooks a leaping mountain brook, deep enough to dunk in. Then pass through the strap-hinged front door and into a glowing pine-panelled great room with giant windows, a big wood stove, 3 Chesterfield couches, dining area and kitchen. You see the forest all around you, but you're inside, ready to unwind. Upstairs, the loft features the master bedroom (sleeps 2, queen) and a reading/games room (can sleep 2, futon). Walking into the ell, you pass the bathroom, the 'room with no purpose,' and the guest bedroom (sleeps 2, futon) which opens onto the back deck, where the barbecue is, and the sound of the leaping waters. In summer the lawn is thick and lush, and you are surrounded with pines, birches, maples and mountains. Chauncey Brook forms the east border & offers a serene and ferny welcome; overlooking it, there's a beautiful firepit surrounded by log benches. The southern border is the Dead Branch Brook with its refreshing plunge pools. About a 1/4 mile downstream it joins the East Branch of the Westfield River, a federally-designated 'Wild and Scenic River.' We will provide you with maps and information about the area, which contains extraordinary opportunities for picnicking, fishing, hiking, biking, swimming, x-country skiing, snow-shoeing, photography and painting. And being alone, with someone you want to be alone with. This property is designed to inspire the maximum enjoyment of the 15+ square miles of open space that begins at its doorstep. The Glow Room is a launching pad. To amplify the quiet and help you unplug, there is no internet service (bring DVDs for your laptop). New cell phones work, but will drop out.

Top guest favourite

Apartment in Williamsburg

4.95 out of 5 average rating, 114 reviews

The cozy clubhouse

Take a break and unwind at this peaceful cozy studio apartment with a private deck looking out over the garden and classic New England stone wall. Located on a quiet dead end street in the village of Haydenville. Not far from the local rail trail, hiking trails, and only a 13 minute drive to downtown Northampton. Very close to Look Park and Valley View Farm common wedding venues. A gateway to the Berkshires, with easy drive access to the Tanglewood music venue, Mount Greylock, and Mass MOCA.

Top guest favourite

Guesthouse in Cummington

5 out of 5 average rating, 129 reviews

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Top guest favourite

Cabin in Cummington

4.98 out of 5 average rating, 230 reviews

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Top guest favourite

Guest suite in Williamsburg

4.98 out of 5 average rating, 279 reviews

Happy Maples!

I am a custom builder and I decided to have some fun building out my own special guest space. Welcome to Happy Maples! The suite is a private 600 sq ft hand crafted studio with private entrance, bath w/shower, large deck w/Adirondack chairs and grill, views of the gardens and 100' from the historic Mill River right behind the house. There is a queen bed and an additional twin memory foam bed available. 12 mins to Northampton, 20 mins to Amherst, Bike trail in back yard. Come for a fun visit!

Top guest favourite

Cabin in Williamsburg

4.97 out of 5 average rating, 109 reviews

Mountain Retreat close to Northampton & Amherst!

Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

Top guest favourite

Home in Williamsburg

4.99 out of 5 average rating, 204 reviews

Hilltown Studio

Stunning 2nd floor studio (limited kitchenette with easy to prepare Breakfast foods provided) close to Northampton, Smith and the Five Colleges, scenic drive to the Berkshires, one mile to the Snow Farm and just minutes to Valley View Farm. Lovely space & private deck overlooking perennial gardens & wildlife wandering by. Perfect stop when traveling through Western Mass, touring local colleges or a trip to enjoy the music, museums and restaurants in the Pioneer Valley and Berkshires.

Guest favourite

Camper/RV in Westhampton

4.89 out of 5 average rating, 204 reviews

AirbytheStream waterfront, private, clean and cozy

Beautiful private camper with outdoor deck on the water. All the creature comforts but half the price. Very private yet 15 minutes to Northampton or Easthampton. Kitchen sink, 2 burner stove, refrigerator, toilet and shower, one queen bed and twin bunk beds, dinette can also turn into a bed. Pots and pans, silverware and cooking utensils are provided. Camper has power and water as well as heat and air conditioning. There is a Blackstone griddle for outdoor cooking.

Top guest favourite

Apartment in Plainfield

4.97 out of 5 average rating, 281 reviews

Sunny, light filled loft in 1873 Colonial

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

Top guest favourite

Apartment in Conway

4.96 out of 5 average rating, 188 reviews

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

Top guest favourite

Apartment in Northampton

4.99 out of 5 average rating, 190 reviews

Cozy Haven: Convenience & Charm

Welcome to our charming Florence, Massachusetts Airbnb! Only 10 minutes from downtown Northampton, our newly renovated property blends comfort, convenience, and natural beauty. Our location provides swift access to Northampton's vibrant heart. Within a 10-minute drive, you'll be amid bustling streets with eclectic shops, superb dining, and a lively arts scene. Explore boutiques, galleries, and cafes that define Northampton's creative and entertaining spirit.

Top guest favourite

Cabin in Chesterfield

4.97 out of 5 average rating, 114 reviews

Hilltown Cabin Hideaway: A River Runs Through It!

Rediscover peace in the Hilltowns of Western Mass. Charming 3BR cabin in nature, with full kitchen, bath, laundry, TV and Wifi! Relax in a serene, wild and beautiful place. Cook a meal with friends. Take a riverside hike, or explore an Old Growth Forest nearby. Go fishing. Watch fireflies. Jump in a swimming hole. Lie in the meadow. Watch the clouds. Enjoy the Hot Tub for two. *Breath the free air again!*