Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

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Guest favorite

A serene river scene is depicted, surrounded by dense greenery and trees. The still water reflects the landscape, with smooth stones visible along the shoreline. Soft light illuminates the area, highlighting the natural beauty of the setting.

Cabin in Chesterfield

4.91 out of 5 average rating, 114 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 favorite

A functional kitchen is showcased with custom wood cabinetry and a dark countertop. An electric stove and an overhead vent are visible, alongside open shelving displaying bowls and kitchen items. Natural light enters through a large window above the sink, illuminating the vibrant yellow walls.

Apartment in Leeds

4.98 out of 5 average rating, 150 reviews

Private Studio for a Sweet Getaway!

A cozy, comfortable, studio flat with ready access to local music venues and restaurants. Downtown Northampton is 15 mins by car or a 1/2 hr bike ride. We abut the bike path and there's a Valley Bike Share kiosk nearby. Ideal overnight spot for visiting Smith and other area colleges or for attending workshops at Snow farm. Easy day trips the Berkshires. Plenty of area hiking! Perfect personal retreat spot! I accept dogs on a case by case basis, small dogs preferred and I cannot accept cats.

Top guest favorite

Farm stay in Williamsburg

4.98 out of 5 average rating, 114 reviews

Charming, updated , 3 bedroom farmhouse farm stay

Enjoy a tranquil stay on a small farm. Enjoy sunrises across the fields and rolling hills while sipping your morning coffee. Enjoy beautiful evening skies while sitting around the fire pit. Mingle with the goats and ducks (fresh duck eggs are usually available for purchase). Conveniently located to Northampton, Amherst, the 5 colleges, restaurants and family activity. We are right next door to Snows Craft Farm and a few miles from Valley View Farm, Quonquont Farm and Look Park Concerts!

Top guest favorite

An open door reveals the entryway of a rustic cabin. A patterned rug leads into a softly lit interior, where a cozy bed is visible in the background, framed by natural wood accents and windows that invite the outside in.

Cabin in Cummington

4.98 out of 5 average rating, 213 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 favorite

A spacious deck is surrounded by rustic wooden siding, featuring a circular table covered with a blue and white checkered tablecloth. Two Adirondack chairs, a grill for outdoor cooking, and potted plants offer a welcoming space beneath the shade of a large tree.

Guest suite in Williamsburg

4.98 out of 5 average rating, 266 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 favorite

A deer is seen partially hidden among lush, green foliage, with long, slender plant shoots reaching upwards. The background features a rustic wooden structure with a darkened entrance, contrasting with the vibrant greenery in the foreground.

Home in Williamsburg

4.99 out of 5 average rating, 189 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 favorite

A serene woodland scene features a gently flowing stream surrounded by lush greenery. Smooth rocks are partially submerged in clear water, while fallen logs create natural bridges over the stream. Sunlight filters through the canopy, illuminating the vibrant foliage.

Camper/RV in Westhampton

4.89 out of 5 average rating, 171 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.

Guest favorite

Apartment in Plainfield

4.97 out of 5 average rating, 271 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 favorite

The image showcases a serene river scene with colorful autumn foliage framing the landscape. In the background, charming buildings with warm hues line the waterfront, while the calm water reflects the vibrant colors of the trees. Gentle hills rise in the distance.

Apartment in Conway

4.95 out of 5 average rating, 165 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 favorite

The entrance features a welcoming porch with a black bench positioned next to vibrant greenery. A climbing plant is showcased in a white pot, while colorful flowers border the stone pathway leading to the front door, which is framed by classic blue shutters.

Apartment in Florence

4.99 out of 5 average rating, 157 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 favorite

A spacious living area features wooden walls and a vaulted ceiling with exposed beams. A comfortable sectional sofa and a coffee table are positioned on a patterned rug. A stone fireplace is visible, alongside a kitchen with bar seating and various amenities.

Cabin in Chesterfield

4.98 out of 5 average rating, 106 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, safe 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!*

Superhost

The interior space features high wooden ceilings and large windows allowing natural light to filter in. A cozy seating area with a spacious gray sofa faces a wood stove. A dining area and an outdoor deck are visible through sliding glass doors.

Cabin in Plainfield

4.92 out of 5 average rating, 170 reviews

Peaceful Cabin in the Woods

Escape the noise and come relax in the middle of the beautiful Berkshire Hills. This classic log cabin has been recently renovated so that you can unwind and connect to the picturesque landscape that envelopes this property. You can drive 30 minutes west to North Adams and visit Mass Moca or 30 minutes east to Northampton, Amherst & Hadley. (Please note, 1/2 of the bedrooms is an open loft).

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Other great vacation rentals in Chesterfield

Guest favorite

The front porch features a cozy seating area with cushions on a wooden bench, accompanied by a small table. Potted plants add greenery to the entrance, and bright natural light filters through the surrounding trees, enhancing the welcoming ambiance.

Apartment in Conway

4.96 out of 5 average rating, 25 reviews

Spacious, Sunny* Woodland Retreat

MollyRating, 5 stars4 days ago

We had a fantastic stay at Erica's with our 2 month old. Erica provided a crib, and it was safe for infant sleeping. We enjoyed sitting on the porch, and ended up cooking a full dinner for local friends one night. The kitchen had all the basics that we needed. It was a short trip so we didn't have much time to explore the property, but it looked beautiful and we enjoyed hearing the frogs at night and birds during the day. The apartment is HUGE, and we found it very comfortable. It'll be our go-to for future visits in the area!

Top guest favorite

An A-frame cabin is illuminated at night, featuring warm string lights adorning its exterior. A wooden deck extends from the cabin, accompanied by a picnic table positioned on the ground level. The surrounding environment exhibits a tranquil forest ambiance.

Cabin in Becket

5 out of 5 average rating, 5 reviews

WALK to lake! Dog friendly, A-Frame in Berkshires!

AustinRating, 5 stars1 week ago

What more could you want? This quaint cabin situated in the woods offers privacy, unique architecture, comfort, and peace. It’s equipped with everything you could possibly need, and the hosts were truly some of the most responsive and kind people I have ever interacted with. They truly went above and beyond for us. We stayed with a toddler and two dogs, and they all loved the property and the cabin. We will most definitely be back!

Guest favorite

A spacious dining area features a long table draped in a vibrant yellow tablecloth, surrounded by wooden chairs. An antique fireplace is visible, complemented by candles and decorative elements. A sideboard displays glassware and a portrait, enhancing the historic ambiance of the room.

Home in Ashfield

4.98 out of 5 average rating, 57 reviews

An 18th century farmhouse

NateRating, 5 stars5 days ago

What a beautiful, idyllic getaway Susan offers for her guests. A kind welcoming soul who provides a stay that brings you back in history – we had the most lovely time!

Guest favorite

Cabin in Cambridge

4.97 out of 5 average rating, 31 reviews

Pond View Cabin. Off-Grid, Rustic & Dog Friendly.

EmilyRating, 5 stars1 week ago

Highly recommend Brian’s off grid cabin! His directions were very helpful and made navigating the generator, camp shower, and other on-site details super easy to understand and execute. His property is beautiful and peaceful. We’re already looking at our calendars for another time to visit. Our dog, Stumpy, very much enjoyed the outdoor access and pond. He didn’t want to leave!

Superhost

Two wooden Adirondack chairs are positioned invitingly next to a rustic fire pit, which is surrounded by stones. A stacked pile of firewood is nearby, nestled among the greenery of the forested surroundings.

Cottage in Williamsburg

4.75 out of 5 average rating, 73 reviews

A Place for Peace - perfectly imperfect!

JenRating, 5 stars8 months ago

Comfortable with beautiful surroundings. Very responsive host.

Top guest favorite

A classic New England farmhouse is framed by lush greenery, with expansive blue skies and soft white clouds overhead. The image captures the farmhouse's white exterior alongside two large barns, all surrounded by well-kept fields and trees in a serene countryside setting.

Home in Chesterfield

4.98 out of 5 average rating, 58 reviews

High Field Farm

CatherineRating, 5 stars1 week ago

Such a relaxing place, space for everyone to spread out and to gather…kids played in the barn because it was a rainy weekend and sadly too cold for a swim. Great kitchen with all necessities. four minutes to gorge trail head where my son ran 50 miles in the beast coast ultra. highly recommend

Guest favorite

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

4.92 out of 5 average rating, 49 reviews

Vermont Mirror House

GeorgeRating, 5 stars5 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.

Top guest favorite

Apartment in Conway

4.99 out of 5 average rating, 95 reviews

House Above the Hollow

AnnaRating, 5 stars2 weeks ago

Meg’s place was truly amazing. The apartment itself was very well maintained, well-appointed, and Meg went out of her way to ask what kind of milk/creamer we liked with our coffee so that she had stocked in our fridge upon arrival. The property is stunning- from Meg’s flower beds to her gardens, to the open fields, to the bird feeds attracting the most beautiful birds, this property is truly serene and a place where we felt relaxed. Our visit was filled with hiking, biking, and exploring nearby towns (Northampton, Amherst, Hadley, etc.). Meg herself is an incredibly talented artist and has beautiful pottery she crafts in her studio located under the apartment. She was kind enough to show us the studio and sell us a couple of her beautiful vases which we know we’ll always think of our wonderful trip whenever we see them. Thanks for everything, Meg!

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Vacation rentals in Chesterfield

Top-rated vacation rentals in Chesterfield

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Popular amenities for Chesterfield vacation rentals

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