
Vacation rentals with a fireplace in Chester
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Top-rated fireplace rentals in Chester
Guests agree: these fireplace rentals are highly rated for location, cleanliness, and more.

Boulder House - Extraordinary Luxury in the Woods!
From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Handmade 3 Bedroom Log Cabin | 5 Min From Skiing
Wake up to brisk mountain air with a cup of coffee and moose in the front yard... This house is a sanctuary, ideal for ski trips, hiking, leaf peeping, wine, beer, and cheese tasting, shopping and sugar house adventures. This is a place to unwind with friends and family. Sit in front of the cavernous fire place and watch the flames twist up the 18ft, handmade, stone hearth. With three private bedrooms, two bathrooms, a futon, and 10ft dining table, this house comfortably sleeps and feeds 8.

Fat Cat Barn - Close Okemo & Magic, Vermont
Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

Riverbed Treehouse @hot tub & a new sauna & views!
The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

Tiny Home w/ Parking - Pet Friendly & Fireplace!
Beautiful Bellows Falls Tiny Home named Sky’s the Limit! Anything is possible here. Please join us in the first ever unveiling of Airbnb for this quaint tiny home! It is near a plethora of shops and restaurants in the historic town of Bellows Falls. Explore for yourself, or bask in the heat of the fireplace inside the house and fire pit outside. For hikers and skiers, this home is a hidden gem. Okemo is just 37 minutes driving, and there are scenic running paths and hiking spots within town!

New Cabin in Jamaica
Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Stunning Okemo Views - 3BD 3BA on 10 Private Acres
Recently constructed on ten private acres with captivating views of Okemo. Three BR, three full bath, air conditioned modern chalet, just 1.5 miles from downtown and 3 miles from Okemo’s base areas. Epic views of Okemo and surrounding mountains from every room. Cozy around the fireplace in the living room or enjoy smores outside by the firepit, or unwind on the deck. Lower level has second living room great for kids with large TV, comfy couches, Pac Man arcade, foosball and board games.

Treehouse Haven in Putney-All Seasons
Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting toilet ☽ Tea & local coffee ☽ Hot outdoor shower ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Visit for romance, time with the family, a retreat from the business of life, or even a remote work sanctuary.

Ogden's Mill Farm
Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Peaceful Ludlow Base 5 minutes to Okemo
Newly renovated, clean 1 BR apt. in historic house 2 blocks to town, 5 minute drive to Okemo, Buttermilk Falls, and 2 minute walk to the Ludlow Farmers Market. Enjoy complimentary coffee and local maple syrup while overlooking the town of Ludlow. Make yourself at home with a full kitchen/bath, wall-mounted flat screen TV, king bed, and comfortable futon. Free EV charging available. Kayaking, hiking, and golfing close by. We are dedicated to ensuring a top-notch experience!

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.

Quaint stone house!
⭐️ 2022 Rockingham Old House Award ⭐️ Take it easy at this unique and tranquil getaway. The Cairn of Vermont is an 1840s stone house located in the sleepy remnants of Bartonsville Village, now part of Chester, VT. 20 minutes to skiing and hiking, biking and the great outdoors are all around you! Less than 5 minutes to Vermont Country Store and make your way home through the Bartonsville Covered Bridge!
Popular amenities for Chester fireplace rentals
House rentals with a fireplace

Clean, Captivating VT Farmhouse near Stratton!

Cozy Modern Sugar House with spectacular views.

The Post Haus: one-of-a-kind modern VT experience

Modern 3-bedroom A-frame in Londonderry w/ Pond

Lovely Brick Schoolhouse

Comfortable farmhouse with stunning views

The Grafton Chateau

Stylish Ascutney Cabin with Mountain Views
Apartment rentals with a fireplace

Suite Sunset 311 Rice Lane Bennington VT

"The Parlors"

Suite 23 - Spacious Sunny 2-BR with Mountain view

Minimal organic hideaway inspired by nature

Apartment in Vermont Historic Home

Brian Peace of Heaven

The Shepherd's Retreat

Killington Skyeship 4 BR | 1 Min Gondola + Hot Tub
Villa rentals with a fireplace

Private Wing of largest Colonial Mansion in US

Pico D305 located slope side at Pico quiet area

Sunrise East Glade C8

Sunrise Timberline I7

Whiffletree base of Killington outdoor pool

Stonehouse at Stratton

Base of Killington with Sports center access

Vermont Vacation Villa—Grapevine Getaway
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $224 | $257 | $212 | $209 | $198 | $200 | $253 | $240 | $238 | $260 | $230 | $247 |
| Avg. temp | 23°F | 25°F | 33°F | 46°F | 56°F | 64°F | 69°F | 67°F | 60°F | 49°F | 39°F | 29°F |
Quick stats about vacation rentals with a fireplace in Chester

Total vacation rentals
Explore 50 vacation rentals in Chester

Nightly prices starting at
Chester vacation rentals start at $70 per night before taxes and fees

Verified guest reviews
Over 1,620 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Chester vacation rentals include wi-fi access

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

4.9 Average rating
Chester stays are highly rated by guests—averaging 4.9 out of 5!
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Dorset Field Club
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Hooper Golf Course
- Bromley Mountain Ski Resort
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Whaleback Mountain
- Ekwanok Country Club
- Brattleboro Ski Hill
- Fox Run Golf Club
- Montshire Museum of Science
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