58 Resorts/Retreats near Chester, VT

Springfield, VT  
Capacity: 580
New England style country inn, modern motel annex - .25 mi from center of town.
Walpole, NH  
Capacity: 250
Alyson’s Orchard is a unique, 500 acre working orchard and year-round event and conference center in the heart of historic New England. Experience country elegance as you host your destination wedding, family reunion, corporate retreat or other special events in our stunning reception hall or am
Windsor, VT  
Capacity: 200
Nestled on historic main street, Snapdragon Inn offers the modern amenities of a small luxury inn located inside one of the most well known homes in the Upper Valley. The former estate of Maxwell Perkins (editor of Hemingway, Faulkner, and others) and William Maxwell Evarts (US Secretary of State,
Windsor, VT  
Capacity: 300
The Windsor Mansion Inn is a 14,000 square foot colonial mansion situated high on a 14 acre private hill overlooking the Connecticut River valley, Cornish Hills and village of Windsor. Views from our patio, event deck, promenade and expansive lawn are the most breathtaking in Southern Vermont.
Bondville, VT  
Capacity: 400
South Woodstock, VT  
Capacity: 90
Step back in time, here at The Kedron Valley Inn. We are a quaint, historical Inn and Restaurant located in the foothills of this equestrian area. Built in 1828, there is a 2 acre swimming pond, lush gardens, walking trails, biking and relaxation. Our front porch serves as a great spot for al f
Hartland, VT  
Capacity: 200
The Sumner Mansion Inn is a completely restored Federal Mansion built in 1807 that features antique furnishings in our public spaces and lodging rooms. We have a library/solarium wing that seats 88 for dining, 120 for roaving cocktails. We have two exterior patios and a Tent Pavilion that seats
Cuttingsville, VT  
Capacity: 150
Experience casual elegance at our Vermont inn, nestled in the glorious Green Mountains. Enjoy the comforts of home while we provide exceptional hospitality. Choose from one of our deluxe cottages for your getaway, complete with modern amenities and luxurious linens. Nestled on 120 acres, you can exp
Woodstock, VT  
Capacity: 120
Bed and Breakfast at historic farmhouse with indoor and outdoor event spaces for weddings, parties, reunions. Spectacular setting for tented outdoor events. Private and unique corporate retreats and offsite meetings.
Woodstock, VT  
Capacity: 18
A contemporary 'green' inn which has won many awards and is very ecologically/organically aware. The inn is the antidote to 'Ye Olde England'.
Woodstock, VT  
Capacity: 250
Victorian farmhouse, warm and homey with a touch of elegance - US Route 4 W.
Manchester Center, VT  
Capacity: 200
Located on Historic Route 7A, just one mile north of Manchester Center,VT the Casablanca Motel is a unique lodging experience. 10 individually themed cabins, situated on 3 acres of land, offer a quiet night's rest after a busy day in Southern Vermont. We are close to the Designer Outlet stores as we
Sunapee, NH  
Capacity: 225
Dexter's Inn is an affordable, family-friendly country estate near Mount Sunapee and Lake Sunapee that combines the charm & hospitality of a bed & breakfast with the on-site activities & services of a small resort. Our inn is a special country resort-inn, blessed with an amazing view and idyllic gro
Manchester, VT  
Capacity: 200
Tudor-style Inn & Cottages (1950s) on spacious grounds offering lovely mountain & valley views.
Killington, VT  
Capacity: 1000
The Killington Grand Resort Hotel Conference Center and Spa is Killington's only full-service mountainside hotel featuring 15,000sq’ of meeting space, hotel rooms, studios, suites and penthouses. Rendezvous Lounge, Ovations Restaurant, Spa, Health Club with 2 outdoors Jacuzzi and large year round st
Killington, VT  
Capacity: 80
Modern 3-story Lodge situated adjacent to ski slopes, 20 miles from Rutland Airport.
West Dover, VT  
Capacity: 1700
West Dover, VT  
Capacity: 75
Grantham, NH  
Capacity: 199
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Rutland, VT  
Capacity: 400
Ideally situated in the heart of Vermont, the Holiday Inn Rutland/Killington is centrally located with easy, scenic access to Vermont's many historical, cultural, shopping and recreational attractions. *Wedding and Banquet Facilities for up to 500 persons *151 Guest Rooms *Pet Friendly *On sit