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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.

  • 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 is true Vermont. A two minute walk will find an authentic Scottish Pub or the village green. Guests love our large family room with wet bar, TV, pellet stove and foosball; two additional living rooms, working fireplace, furnished outside porch, well stocked kitchen, Fios, backyard, barbecue, lawn games and ample parking. We are in the midst of 5 ski areas, and plenty of hiking trails and outside activities abound!

    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!”

  • 1850's Restored Victorian in Downtown Chester
    SUPERHOSTEntire house · 6 guests · 4 beds · 1.5 bathrooms
    1850's Restored Victorian in Downtown Chester

    The Amare Guesthouse is a relaxed and inviting restored Victorian home, steps from downtown Chester VT. Walking distance to restaurants and pubs, rivers, farms, trails, antique shops, galleries, and a grocery store. Relax on one of the large porches for coffee or cocktails.  Enjoy small town life, explore Vermont’s famous hiking and skiing, or cook in the gourmet kitchen. Our intent is to provide a space that allows you to rest, nourish, and play. See renovations on instagram: @amareguesthouse

    What guests are saying:

    “This lovingly restored 1850s Vermont farmhouse will not disappoint. Staying at this home will surely be the highlight of your trip (second only to the beauty of the changing leaves). Krystina and Doug are wonderful hosts and live nearby in case you have any questions. Communication was fantastic and the recommendations for local places to visit was invaluable. My family and I enjoyed a reunion at this home and staying here worked out perfectly for that purpose. We hope to return one day!”

  • Beautiful 1BD Apartment w/ Mtn view
    SUPERHOSTEntire flat · 4 guests · 3 beds · 1 bathroom
    Beautiful 1BD Apartment w/ Mtn view

    Beautifully decorated 1st floor apartment, private entrance, queen bed, pullout couch in living room, full bath, kitchenette, deck with mountain view in heart of Vermont woods, trails for year round recreation near charming towns with A+ restaurants, skiing, shopping, all you can imagine for a great Vermont year round getaway. For winter snowmobilers the VAST snowmobile trail is accessible from our property as are trails for XC skiing and snowshoeing.

    What guests are saying:

    “Hugh and Nancy’s ‘Granny Flat’ was the perfect landing zone after a day skiing at Okemo. It’s peaceful and remote yet a 10-15 minute drive to lots of great attractions and restaurants. The property was fun to explore with a neat hike and maple syrup sugar operation on site. We would definitely recommend staying here!”

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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

1880 Chester Farmhouse - Suite
SUPERHOSTPrivate room
1880 Chester Farmhouse - Suite
Price:€61 / night
1868 CARRIAGE HOUSE-COZY VERMONT AUTUMN GETAWAY!
SUPERHOSTEntire guest suite
1868 CARRIAGE HOUSE-COZY VERMONT AUTUMN GETAWAY!
Price:€119 / night
VT Village Home - Ski, Hike, Bike & Relax
SUPERHOSTEntire house
VT Village Home - Ski, Hike, Bike & Relax
Price:€137 / night
Cozy Village Cottage
SUPERHOSTEntire cottage
Cozy Village Cottage
Price:€102 / night
Private Hilltop farm apartment
SUPERHOSTEntire house
Private Hilltop farm apartment
Price:€69 / night
Inviting studio apartment above barn in Vermont
SUPERHOSTBarn
Inviting studio apartment above barn in Vermont
Price:€62 / night
Private Cabin / Minutes to Okemo
SUPERHOSTEntire cabin
Private Cabin / Minutes to Okemo
Price:€84 / night
The Stone Schoolhouse
SUPERHOSTEntire cottage
The Stone Schoolhouse
Price:€88 / night
Spacious King Suite w/ Breakfast Hills Of Weston
SUPERHOSTPrivate room
Spacious King Suite w/ Breakfast Hills Of Weston
Price:€119 / night
Apple Blossom Cottage: A Tiny House
SUPERHOSTTiny house
Apple Blossom Cottage: A Tiny House
Price:€114 / night
Cozy & Bright Log Cabin | 8 Minutes to Okemo
SUPERHOSTEntire cabin
Cozy & Bright Log Cabin | 8 Minutes to Okemo
Price:€199 / night
Private Apt on Farm, Magnificent Views, Hot Tub
SUPERHOSTEntire flat
Private Apt on Farm, Magnificent Views, Hot Tub
Price:€115 / night
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