A room with calming earth tones. This is a medium sized room with one queen and one full double bed, private bathroom with shower and air-conditioning for hot weather days. This listing is an option for renting an individual room in the Inn. The entire Inn can be rented as well. Please check our...

Overlooking the village green, this bright and spacious room accommodates a family or group of people. Has two queen-sized beds and a love-seat sleeper sofa with a twin bed. Has wall-to-wall carpeting, private bath with shower and air conditioning for hot weather days. Also features a infrared...

The 1843 Stone House is a pre-civil war home that is quaint and comfortable for 2 families or 3 couples. The house is full of charm while also providing modern amenities. The Chester Village green is a short walk from the house where shops and restaurants are housed in buildings from yesteryear....

This 4-bedroom, 1.5-bath vacation rental house in Chester provides a charming farmhouse setting for your next Northeast escape! Situated on 13 acres shared with Gordon's Christmas Tree Farm, this scenic property dazzles you with natural beauty during every season! See if the fish bite at the nearby...

Beautiful contemporary mountain home in Vermont sitting in 150 acres of private land. Borders a State Park with beautiful trails and an 80 ft Cascade. 5 Bedrooms, sleeps up to 12. This sprawling home features a large kitchen, separate dining room, spacious living room with stone fireplace and...

Moonlight View Experience a Vermont vacation from the pages of a magazine at this three-bedroom Windham home, a secluded country house with an open living space, an expansive deck and yard, and nearby access to picturesque villages, hiking trails, and ski slopes! This home sits on a grassy,...

Castle Hill Condo This beautiful Cavendish townhome features updated furnishings and is located close to everything Okemo and Ludlow have to offer. This rental showcases a spacious kitchen with granite countertops and stainless steel appliances. Guests are sure to enjoy the large living area on the...

Depot Street Condo This budget-friendly and recently updated 1920s condo is located on the Villiage Green and is just five miles from Okemo and everything it has to offer. There is an open floor plan through the kitchen, dining room, and living room, so it's easy to socialize with your group. The...

Cozy in Cavendish Find a quintessential Vermont escape at this bright and inviting home in Cavendish, a peaceful retreat among the evergreens with beautiful exposed beams and natural wood details. Spend your days skiing, snowboarding, snowshoeing, or hiking, and return home to luxuriate in the...

Our home is a beautiful 3 bedroom, 2 bath with large family room and sleeps 10. In winter we are 4 minutes to skiing at the fabulous resort of Okemo/Jackson Gore. You ski, board, ice skate, snowmobile, snow shoe, cross country or go to the spa for a day of fun. At our house we have an outdoor hot...

Our home is less then 10 minutes to the base of Okemo Mountain yet it's in a secluded quiet development. This spacious home has 4 bedrooms and 2 1/2 baths. There is plenty of seating in the kitchen and dining room. There are TV's int he family room as well as the master bedroom and one queen...

The Vermont 1828 Reunion House is a Historic Farmhouse 5 miles from Okemo Mountain Resort. Featuring 8 bedrooms, 4 baths, 2 kitchens, 2 living rooms, and sleeping for 20, Bed linens and towels are provided by our housekeeping pros. This is the place for Making Memories with Friends and Family in...

This is an exclusive Tentrr site. Tentrr partners with farmers, ranchers, and other property owners to offer unique outdoor accommodations on beautiful private land. Each Tentrr Signature site includes a 10'x12' safari-style canvas tent on a raised platform, and you'll find a queen-size single or...

The property includes 7 bedrooms (robes, bath amenities, tempurpedic beds, fireplaces, vable television, DVD and ensuite baths in all but 2), 8-person hot tub, dining for 24. Great for large groups or big families or specialb events. Warm weather Rustic Barn with bar can seat up to 115 guest...

*NOTE: The homeowner lives on site, in a completely separate unit out of sight* Sitting on a plateau above the Williams River you'll find the 'Smokeshire Hilltop Farmhouse,' a 5-bedroom, 2-bathroom vacation rental home in Chester. This 3,000-square-foot classic farmhouse for up to 14 sits on a...

The Windham Country House, a spacious contemporary home, sits on a secluded country road, providing you with peace, privacy and beautiful scenery, while being near many of southern Vermont's activities. GREAT ACCOMMODATIONS The Windham Country House has five large, lovely bedrooms and three full...

Step back in time when you stay at this authentic, newly renovated 1950’s farmhouse nestled in the Green Mountains of Southern Vermont! This modern 3-bedroom, 2-bath Vermont vacation rental home offers a quintessential homestead experience for up to 8 guests throughout 2,700 square feet of luxury....

This cute Vermont farmhouse is just 10 minutes to Magic, 20 minutes to Bromley and 25 minutes to Stratton. On the main level there is the master bedroom with a full bath, kitchen, dining, and large living area with a comfortable fireplace and a bonus woodstove to keep you extra warm during those...

Find a home-away-from-home hidden in the trees when you venture to this 2-bedroom, 1-bathroom vacation rental house that sleeps up to 6 guests in Grafton! Architecturally designed and beautifully unique, this cottage is a picture-perfect scene, secluded from the bustle of the big city so you can...

Rest, relax, and enjoy the tranquil surroundings when you visit this vacation rental home in Chester, Vermont! The stunning house has 4 bedrooms, 3 bathrooms, and boasts exposed beams, wall-to-wall windows, and vaulted ceilings. Complete with an immaculate yard, the property features a private...

Spacious, private and fully outfitted for a group getaway to Vermont, this 3-bedroom, 3-bath vacation rental is ready for 4 seasons of adventures! Set on 4 private acres with a wraparound deck for summertime relaxation, and a floor-to-ceiling stone fireplace for staying cozy in the winter, this...

Leave the bustle of the city behind for a getaway at 'RiverLedge Farms!' This 2-bed, 2-bath vacation rental will transport you back to simpler times, where you can sip tea on the front porch, sunbathe in the backyard and look out onto acres of farmland from every corner of the property. When you're...