Vacation rentals with a fireplace in Chester

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Top-rated fireplace rentals in Chester

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Guest favorite

Barn in Andover

4.98 out of 5 average rating, 109 reviews

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

Aug 8 – 15

G$62,408 GYD per night

Guest favorite

Cabin in Bradford

4.98 out of 5 average rating, 333 reviews

Deer Valley Retreat, Lovely Log Cabin

This Lake Sunapee Region cabin retreat is perfect for romantics, artists, writers, outdoor enthusiasts, gardeners, friends, & family. Centrally located between the area's best lakes and mountains, convenient to area attractions, and outdoor activities. Still, the cabin feels like a destination in itself, where you can relax, recharge, and reconnect. Cozy up by the stone fireplace, relax on the porch, see nature, read, listen, play, cook, stargaze, and enjoy just being! M&R license #: 063685

Dec 27 – Jan 3

G$30,032 GYD per night

Guest favorite

Condo in Killington

4.95 out of 5 average rating, 130 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

Aug 5 – 12

G$20,822 GYD per night

Guest favorite

Tiny home in Wilmington

4.99 out of 5 average rating, 141 reviews

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!

Sep 9 – 16

G$45,793 GYD per night

Guest favorite

Cabin in Jamaica

4.99 out of 5 average rating, 185 reviews

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.

Jul 28 – Aug 4

G$30,735 GYD per night

Guest favorite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 431 reviews

Mahalo Temple Retreat

Retreat in Mahalo's beautiful, private sound healing temple surrounded by nature, amongst streams, berry bushes, fruit & nut trees, medicinal plants and veggie gardens. We are set back just enough from a main road to find your serenity and yet close enough to civilization for human interaction and trails for hiking. Quiet and peaceful location just a few min off I-91 and just over 2 miles from the center of Brattleboro. A fun and quirky town with art cafes, restaurants, and great shops.

Jul 7 – 14

G$21,232 GYD per night

Guest favorite

Guesthouse in Wallingford

4.98 out of 5 average rating, 589 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

Jan 31 – Feb 7

G$29,653 GYD per night

Guest favorite

Cottage in Windsor

4.97 out of 5 average rating, 319 reviews

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.

Nov 18 – 25

G$28,211 GYD per night

Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 123 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

Jul 13 – 20

G$21,058 GYD per night

Guest favorite

Home in Grafton

4.92 out of 5 average rating, 186 reviews

Retro Modern Barn Apartment

The vintage barn studio offers an open living plan with Queen bed, fully equipped gourmet kitchen and a cozy seating area w/ fireplace. Once an artist's studio, it is has been painstakingly renovated with a "reduce, reuse, recycle" philosophy. Since a lot of people are asking these days - this barn is suitable for remote work as we have fiberoptic wifi. We have had many guests this year staying for multiple weeks working remotely.

Nov 2 – 9

G$42,008 GYD per night

Guest favorite

Apartment in Weathersfield

4.97 out of 5 average rating, 110 reviews

Cute VT Bungalow With 180 Degree View of NH

Located on a quiet country dirt road you will find this cozy apartment perfect for a weekend getaway. A short walk and you will be amazed at the 360 degree views of Vermont and New Hampshire. Centrally located near Okemo, Sunapee and Killington mountains, ski all 3 mountains in a weekend. Explore covered bridges, walking trails, scenic bike rides, or tubing on the Connecticut River.

Oct 26 – Nov 2

G$42,725 GYD per night

Superhost

Tiny home in Chester

4.9 out of 5 average rating, 154 reviews

Sage House at Camp Greenwood Vermont - w/ sauna!

Welcome to Sage House at Camp Greenwood: a brand new micro tiny house village central to the best attractions in Southern Vermont! Skiing, hiking, dining....and a barrel sauna and private pond available to our guests! As featured on A&E's Living Smaller! Pets welcome with a $100 pet fee.

Apr 4 – 11

G$31,255 GYD per night