Holiday houses in Chesterfield

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Top-rated holiday rentals in Chesterfield

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Guest favourite

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 favourite

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 favourite

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 favourite

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 favourite

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 favourite

Home in Williamsburg

4.99 out of 5 average rating, 190 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

Campervan/RV in Westhampton

4.89 out of 5 average rating, 172 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 favourite

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!

Guest favourite

Apartment in Williamsburg

4.88 out of 5 average rating, 213 reviews

Studio apartment on route 9, "Inn the Valley"

A bright and cozy studio apartment on PVTA bus line just outside of Northampton, MA. Skylight, wood floors, kitchen, and full bathroom as well as heat and air conditioning, oriental rugs and unique furnishings. 10 minutes from Northampton center and 20 minutes from Amherst center. Very convenient for all 5 colleges. Five minutes from Snow Farm Art Institute. Two minutes from Valley View Farm. We are meticulous in our cleaning and disinfecting in the face of Covid-19.

Top Guest favourite

Apartment in Conway

4.95 out of 5 average rating, 166 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 Florence

4.99 out of 5 average rating, 158 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

4.98 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!*

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Other great holiday rentals in Chesterfield

Guest favourite

Cabin in Williamsburg

4.94 out of 5 average rating, 34 reviews

Retreat in the Woods

NicoleRating, 5 stars1 week ago

Our stay at Maya's place was lovely! We were visiting the area for a wedding and wanted to stay somewhere quiet, safe, and peaceful. This place was exactly what we were looking for! Maya was very responsive and the place was clean and cozy. It was super private, felt safe, and was very cozy! We would definitely come back to stay if we are in the area again!

Home in Goshen

5 out of 5 average rating, 3 reviews

Goshen Lake House

AlisonRating, 5 stars3 weeks ago

Kendra's place was pristinely clean and incredibly easy to use. It's an incredibly peaceful, quiet spot and the house is very comfortable, so we had a very relaxing stay. My son goes to school about a half hour away and we rented the place so he could have quiet time to rest and study for exams in a cozy, comfy, homey atmosphere and that is just what we got! The kitchen is well equipped and we were able to cook everything we wanted. We didn't get a chance to use the grill, but it looked great. Kendra was very responsive and communicative and our stay was totally issue-free so we didn't really need to be in close contact through our stay. The house sleeps lots of people and it could be a fun spot for a big family to have some great family-time or a group of friends to catch up. We would definitely return when we have more time to explore the pretty lake nearby and the surrounding area! Thanks Kendra!

Cabin in Chester

4.96 out of 5 average rating, 56 reviews

2 Rustic Cabins on 68 Secluded Acres

DileniRating, 5 stars3 weeks ago

I love the cabin very peaceful and quiet. The host was always attentive to our messages. Will definitely stay here again.

Top Guest favourite

Cabin in Becket

5 out of 5 average rating, 6 reviews

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

FranciscoRating, 5 stars1 week ago

Beautiful little cabin, peacefully in the woods. Great, friendly, and responsive hosts. Perfect location to relax, walk around, find closeby hikes and hidden gems, including some great breakfast spots. 10/10 would recommend.

Guest favourite

Home in Ashfield

4.98 out of 5 average rating, 87 reviews

Magical, Rural Getaway in the Berkshires

SarahRating, 5 stars3 weeks ago

This place was great, I was a little concerned it may be too rustic based on the pictures, but the place was fabulous. No problems with wifi, access, sleeping arrangements. The open space for the kitchen/tv room were so great for our large family. Everything is well appointed, there are clear instructions everywhere on how to use anything in the house. It was really nice for our short weekend stay for graduation. I felt the kitchen was better stocked than most places I've stayed. They had everything we needed. I wish we could have used the fireplace on this rainy cold weekend, but heard maybe it's an Airbnb thing not an owner thing. If you want to head to this area, this was a great place to stay.

Farm stay in Adams

5 out of 5 average rating, 3 reviews

Berkshires/Pet Friendly farm stay w/mountain views

IsabelleRating, 5 stars2 weeks ago

My three friends and I had a wonderful weekend stay at this airbnb. From the start Jessica, the host, was in touch and responsive to any questions I had. The RV itself was perfect, exactly what my group was looking for and was as advertised. A lovely guest-ready camper, a fire pit, great views and outdoor spaces, accessibility, chairs with an umbrella, a picnic table, a hammock that could be set up, easy storage for all of these things, and friendliness from the host next door. We were able to comfortably sleep 4 people for 3 nights. My group have discussed returning when we can because we had such a positive experience. We hope that others will get the opportunity to make memories in Adams, MA as we did during our stay this summer. All I have to say are good things about this location and the people who run it. I would absolutely recommend it :)

Top Guest favourite

Home in Chesterfield

4.98 out of 5 average rating, 58 reviews

High Field Farm

CatherineRating, 5 stars2 weeks 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

Top Guest favourite

Apartment in Conway

4.99 out of 5 average rating, 95 reviews

House Above the Hollow

AnnaRating, 5 stars3 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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Holiday houses in Chesterfield

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