House vacation rentals in Chester

Custom cabin on Mt Ascutney, sweeping Hill Views

Combining sweeping views of distant hills with complete privacy and wraparound porches on two sides, the Red House is a custom cabin built for couples and smaller families. Surrounded by working farms and within easy reach of trailheads to hike or bike Mt Ascutney, or to visit Woodstock, Hanover, Ludlow and the Upper Valley, the Red House sits among some of the best restaurants in Vermont and awaits the discerning traveler who has earned the right to do absolutely nothing and experience it all.

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!

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

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)

4 Bedroom Family Ski House w/ WiFi, cable!

This family heirloom sits tucked away in the trees just off of Chester Mountain Road. Short trips to Bromley, Okemo, Stratton and Magic Mountains. Sleeps 8 comfortably with room for up to 10 on pull out couches. You will fall in love with the retro feel of this house, it's straight out of the 1980's, and has kept that charm over the years. We have consistently updated it with all of the amenities needed to relax, including Air Conditioning, High Speed wifi, Cable, big screen TV and sound bar.

Vermont 1828 Reunion House, near Okemo

The Vermont 1828 Reunion House, close to Okemo is a spacious historic vintage ski lodge and farmhouse with 2 kitchens, 8 bedrooms, 4 baths, & a quintessential Vermont character. Excellent for gatherings & family reunions. Linens & towels provided, beds made. 10 acres, meadow & hidden pond. . A new automatic sprinkler system was installed in 2024 & the house complies with all safety regulations & certified by the town of Chester. Must be 25 years to rent. Long term rentals possible.

Charming Chester Farmhouse Near VT Slopes

Unplug at our spacious 4-bed Chester farmhouse, a four-season retreat minutes from Okemo, Magic & Bromley. Highlights: *Chef’s kitchen & coffee bar *Fast Wi-Fi, dedicated workspace & Smart TV *Spacious backyard for dining & stargazing *Easy 10–20 min to skiing, hiking & local towns *Pet-friendly, family-ready Spend your days hiking, swimming, leaf peeping, or exploring nearby towns. In winter, hit the slopes, then gather for games and a movie. Book your Vermont getaway today!

Birdie's Nest Guesthouse

Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

Mountain views - hot tub, games, minutes to lakes

Enjoy our 3900 square ft home with 5 bedrooms and 3 full bathrooms, large kitchen and dual dining areas. Enjoy the Buck Hunter arcade game, a 75-inch TV, a stocked library and shuffleboard table. Relax in the backyard with a fire or a dip in the Jacuzzi hot tub. Sleeps 12. Explore nearby Woodstock, Manchester and Weston. Okemo & Jackson Gore resorts are less than 10 minutes away. Killington Mtn 30 min drive. Enjoy hiking, fishing, biking, kayaking, skiing & golf nearby.

Charming Vermont Schoolhouse

Kick back and relax in this calm, stylish space. A beautifully restored schoolhouse circa 1860 welcomes you. Situated on a quiet country road this adorable home on one wooded acre has lovely mountain views and a peaceful setting. Nearby you will find skiing, hiking trails and quaint Vermont towns with shops and restaurants. Manchester and Rutland are 30 min. drives, Dorset is just 20 min. Granville NY has a large grocery store and other shops and is only a 15 min. drive.

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

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).

VT Retreat: Hot tub | pool table | 70” TV | bbq

Come and stay in this extraordinary Cavendish home filled with historical charm yet fully updated with all the modern amenities you have come to expect. Our home has everything you need for your getaway. Gourmet kitchen, BBQ, Hot Tub, 2 master suites, games room, pool table, 70" TV, and window A/C's in all the bedrooms. Located just a short drive to many of Vermont's summer and winter attractions.