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Vacation rentals in Chester

Vacation rentals in Chester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Two Beautiful Bedrooms in Mountains
    SUPERHOSTEntire flat · 4 guests · 4 beds · 2 bathrooms
    Two Beautiful Bedrooms in Mountains

    Ready for a Vermont getaway? In heart of ski area w/ A+restaurants & charming villages are two cozy bedrooms on 2nd fl of larger apt complex. Each bedroom has separate toilet/sink room, shared shower room for your and your guests alone. Hallway has washer/dryer, small refrig, coffee maker, microwave, toaster. Not a place to cook but a breakfast nook for sure. Cozy couch area w/ TV.

    What guests are saying:

    “For a look at everyday life in Vermont, Hugh and Nancy's place is nothing short of the perfect place to stay! Tucked away in the mountains, their home provides an incredibly scenic view which can be enjoyed with all the comforts you can ask for: Fully stocked kitchen, cozy seating area, outdoor deck, and super clean sleeping quarters! (Side note - Seeing as we were their only guests at the time, Nancy and Hugh were generous enough to essentially upgrade us to this larger and more spacious accommodation!). One heads up - Their home is up a dirt road so 4x4 or AWD is convenient! This spot is also very convenient for a 5 minute trip into town while also very close to big destinations like skiing, local breweries, and hiking trails. All are go-to attractions when visiting Vermont. For a personal touch, Nancy also leaves a basket of maple syrups for purchase that they tapped on the property themselves - Highly recommended you buy a bottle! :) All and all, an easy recommendation and a place I surely hope to stay again in the future!”

  • Inviting studio apartment above barn in Vermont
    SUPERHOSTBarn · 4 guests · 2 beds · 1 bathroom
    Inviting studio apartment above barn in Vermont

    This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

    What guests are saying:

    “We chose this barn apartment for a ski weekend at Okemo Mountain. The pictures do not do the space justice at all. The drive up to the barn is beautiful in itself. The space is gorgeous, and the details provided by the host (farm fresh eggs! Hershey’s kisses! Coffee! A stocked medicine cabinet with toiletries!) were thoughtful and adorable. The barn is located a short drive to the mountain and the town of Chester has a couple of cute spots to eat (we loved Heritage Cafe for a pre-ski breakfast and coffee). Extra blankets and a postcard view....we loved it so much that we canceled our Airbnb for Burlington next month and rebooked with them for another ski weekend at Okemo next month.”

  • Quintensential Vermont Getaway
    SUPERHOSTEntire house · 14 guests · 12 beds · 4 bathrooms
    Quintensential Vermont Getaway

    In the heart of the village of Chester, our restored 5 bedroom, 4 bath 1820 home offers an amazing Vermont experience!! A two minute walk will find you in an authentic Scottish Pub or on the village green with shops and restaurants. Guests love our large family room with wet bar, TV, pellet stove and foosball table, and two additional living rooms, a working fireplace and a furnished outside porch. We are in the midst of 5 ski areas: Okemo, Magic Mountain, Stratton, Bromley and Killington.

    What guests are saying:

    “The Guy Earle House really can't be beat in terms of coziness, spaciousness, location, and price. We had a big group of friends up for a ski trip to Okemo and the house was the perfect base to fuel up and get all geared up while enjoying each other's company in a picturesque VT village with tons of room to spread out, and it was the perfect landing spot at the end of a big day to cook, play games, sit by the fire, lounge, and sleep in a peaceful house for the next day. The house has more than a large group could ever need, from ample seating areas, linens, dishes and cookware, basic pantry items, and lots of windows to brighten short winter days. Kathy and her husband were super attentive and communicative way ahead of our stay. They were so detailed that we didn't ever need to reach out to them--every need was simply anticipated and taken care of! We'll definitely consider staying here again!”

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Popular amenities for Chester holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chester

Two Beautiful Bedrooms in Mountains
SUPERHOSTEntire flat
Two Beautiful Bedrooms in Mountains
Price:£73 / night
Stone House in a Historic Stone Village
SUPERHOSTPrivate room
Stone House in a Historic Stone Village
Price:£56 / night
Farmhouse retreat w pond & country breakfast
SUPERHOSTPrivate room
Farmhouse retreat w pond & country breakfast
Price:£63 / night
Inviting studio apartment above barn in Vermont
SUPERHOSTBarn
Inviting studio apartment above barn in Vermont
Price:£57 / night
Queen Room with private bath
SUPERHOSTPrivate room
Queen Room with private bath
Price:£73 / night
Country farmhouse minutes from Chester town
SUPERHOSTPrivate room
Country farmhouse minutes from Chester town
Price:£73 / night
Wake up to Mountain views in a Vermont studio Apt.
SUPERHOSTEntire house
Wake up to Mountain views in a Vermont studio Apt.
Price:£53 / night
Charming  2 Bdrm near Skiing and  Village Green
Entire flat
Charming 2 Bdrm near Skiing and Village Green
Price:£85 / night
CARRIAGE HOUSE-COZY SKI GETAWAY! 20 MIN TO OKEMO!
SUPERHOSTEntire guest suite
CARRIAGE HOUSE-COZY SKI GETAWAY! 20 MIN TO OKEMO!
Price:£110 / night
Stone’s Throw
SUPERHOSTPrivate room
Stone’s Throw
Price:£28 / night
Quintensential Vermont Getaway
SUPERHOSTEntire house
Quintensential Vermont Getaway
Price:£147 / night
Beautiful 1BD Apartment w/ Mtn view
SUPERHOSTEntire flat
Beautiful 1BD Apartment w/ Mtn view
Price:£81 / night
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