
Holiday houses in Chesterfield
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Top-rated holiday rentals in Chesterfield
Guests agree: these stays are highly rated for location, cleanliness and more.

Cider House Cottage
Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Peaceful Mill with Waterfall - Home Away From Home
Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated remote workspace

Modern Spacious Home with Mountain Views
Modern Home in Brattleboro with mountain view & many extras: Italian-Marble master-suite, Jacuzzi/Shower for 2, walk-in closet, king bed, grill, heated garage, cable, WiFi. Open-concept living room w/ cathedral ceiling, office, & movie screen. Large open kitchen w/ wine fridge. Second bedroom w/ loft. Explore hiking trails from backyard. Pets ok! 3 mins from Vermont Country Deli & I91 Exit 2. Walking distance to dog park, swimming holes. Downtown: 4 mins Mount Snow: 40 mins Stratton: 54 mins

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!

Spacious Loft with View
Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

Beautiful Timber Frame Retreat
This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

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.

River View apartment
Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by A gorgeous view of the river and mountain across the street .

Log Cabin: Amazing Views, River Frontage, Hot Tub
A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.

Modern Cabin with Outdoor Spa on Vermont Farm
Romantic modern cabin with private hot tub on a 100-acre Vermont farm. This Scandinavian-style retreat features soaring windows, a king bed with luxury linens, a cozy fireplace, and a sleek kitchen. Perfect for couples seeking a peaceful getaway, farm stay, or eco-friendly escape. Soak under the stars, meet our friendly goats, and enjoy the beauty of southern Vermont from your light-filled solar-powered cabin.

Cottage
The "Rustic" cottage is furnished with a queen bed, sofa and dining table. There is a small deck with patio furniture, fire ring with wood supplied, and a gas barbecue. It can accommodate 2 people comfortably. Private with parking. Host in separate house. Wi Fi from Xfinity, but please note that it can be patchy. Roku TV WI FI connected to router.

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.
Popular amenities for Chesterfield holiday rentals
Other great holiday rentals in Chesterfield

Goldfinch Cottage: Timber Frame on 5 Private Acres

Moose Mansion with Paw Pen at Brattleboro KOA

Casita by the Green: Quiet, Country, close to town

Cozy Cottage Loft and Retreat

Artsy & Cozy Cabin - Renovated - River & VT skiing

Cozy Riverfront Cabin-Ski, Swim, Fish, Float, Hike

Woodsy Retreat Near Skiing, Private Pool in Summer

Pondside Retreat in Southern Vermont
Frequently Asked Questions
Are there family-friendly vacation rentals in Chesterfield?
Chesterfield has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in cabin rentals in Chesterfield?
Experience the best of Chesterfield with our cabin rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Chesterfield?
Four-legged friends are welcome in Chesterfield. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there Chesterfield vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Chesterfield, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Chesterfield have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Chesterfield have wifi?
Absolutely! We offer over 10 cabin rentals with wifi in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Chesterfield have free parking?
Absolutely! We offer over 10 cabin rentals with free parking in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cabin Rentals in Chesterfield?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Chesterfield

Total holiday rentals
Explore 50 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $51 NZD per night before taxes and fees

Verified guest reviews
Over 1,430 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Wi-Fi availability
50 of Chesterfield holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesterfield rentals

4.9 Average rating
Chesterfield stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with outdoor seating Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Family-friendly rentals Chesterfield
- Pet-friendly rentals Chesterfield
- Waterfront rentals Chesterfield
- Rentals with a fire pit Chesterfield
- Rentals with lake access Chesterfield
- Rentals with a patio Chesterfield
- Okemo Mountain Resort
- Stratton Mountain
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Mount Snow Ski Resort
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Emerald Lake State Park
- Mount Sunapee Resort
- Mount Holyoke College
- Mount Greylock
- Smith College
- Southern Vermont Arts Center
- Mount Monadnock
- Look Memorial Park
- Camp Plymouth State Park
- Massachusetts Museum of Contemporary Art
- University of Massachusetts Amherst




