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Chester Vermont Hotels & Motels

Find the perfect hotel in Chester using our hotel guide provided below. Find discounted hotel accommodations in or close to Chester, VT for your upcoming individual or group travel. Discover the most favored Chester, Vermont hotel and motel rooms. Browse the Chester area hotels to find the perfect lodging! Please use the provided map of the Chester hotels.

The Chester center is around 7 miles south of Fletcher Fields and 11 miles northwest of Bellows Falls Amtrak.

Chester Hotels/Motels & Accommodations

Grafton Inn : 92 Main St. 92 Main St., Grafton, VT 05146
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~6.25 miles south of Chester
  • 4 star property
  • 3 floors in property
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From$160
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
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Best Western Springfield Hotel - Springfield 818 Charlestown Rd., Springfield, VT 05156
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~8.01 miles east of Chester
  • Midscale Highway hotel
  • Hotel has 2 suites
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From$106
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Castle Hill Resort And Spa 171 Castle Hill Dr., Proctorsville, VT 05153
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~8.66 miles north of Chester
  • Affordable hotel
  • Check in time: 15:00
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From$90
Very Good 4.0 /5 Review Score Call BookMore Details
Pointe at Castle Hill Resort - Proctorsville 2940 State Route 103, Proctorsville, VT 05153
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~8.75 miles north of Chester
  • Midscale Rural hotel
  • Hotel has 2 floors
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From$85
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Rodeway Inn Bellows Falls : 593 Rockingham Rd. 593 Rockingham Rd., Bellows Falls, VT 05101
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~9.58 miles southeast of Chester
  • Two-star Mountain property
  • Check-in time: 11:00
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From$60
Average 3.0 /5 Review Score Call BookMore Details
Blue Gentian Lodge at Magic Mountain - Londonderry 289 Magic Mountain Access, Londonderry, VT 05148
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~9.78 miles west of Chester
  • 3-star Mountain property
  • Free breakfast available
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From$119
Very Good 4.5 /5 Hotel Reviews Call BookMore Details
Harvest Barn Inn : 16 Webb Terrace 16 Webb Terrace, Bellows Falls, VT 05101
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~10.41 miles southeast of Chester
  • Luxurious 5-star hotel
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From$110
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Okemo Mountain Lodging : 77 Okemo Ridge Rd. 77 Okemo Ridge Rd., Ludlow, NY 05149
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~11.34 miles northwest of Chester
  • Mid-scale property
  • Check in time: 0:00
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From$90
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Mountain Lodge at Okemo, A Vail Resorts Property 318 Mountain Rd., Ludlow, NY 05149
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~11.38 miles northwest of Chester
  • 3-star property
  • Check in: 17:00
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From$90
Average 3.0 /5 Reviews Call BookMore Details
Solitude Village at Okemo by Vail Resorts Solitude Rd., Ludlow, 05149
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~12.50 miles northwest of Chester
  • 3-star hotel
  • Check-in time: 17:00
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From$90
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Windham Hill Inn - West Townshend 311 Lawrence Dr., West Townshend, VT 05359
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~12.57 miles southwest of Chester
  • 4 star property
  • Shuttle to airport available
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From$160
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Jackson Gore Village, A Vail Resorts Property 111 Jackson Gore Rd., Ludlow, NY 05149
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~12.63 miles northwest of Chester
  • 3-star property
  • Check-in: 17:00
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From$90
Very Good 4.0 /5 Review Score Call BookMore Details
Royal Inn Claremont 24 Sullivan St., Claremont, NH 03743
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~14.92 miles northeast of Chester
  • Inexpensive hotel
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From$65
Average 3.0 /5 Guest Reviews Call BookMore Details
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Holiday Inn Club Vacations Ascutney Mountain Resort in Brownsville 485 Hotel Rd., Brownsville, VT 05037
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~15.23 miles northeast of Chester
  • Affordable Mountain hotel
  • Hotel has an eco-friendly policy Learn more
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From$120
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Wiley Inn : 2759 Route 11 2759 Route 11, Peru, VT 05152
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~16.14 miles west of Chester
  • Three Star Mountain property
  • Free breakfast
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From$59
Poor 2.0 /5 Guest Reviews Call BookMore Details
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Thoma House 4216 Vt Rte 11, Peru, VT 05152
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~17.49 miles west of Chester
  • High-end Resort hotel
  • Hotel has 2 floors
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From$85
Very Good 4.0 /5 Reviews Call BookMore Details
The Inn at Willow Pond - Manchester 74 Willow Pond Rd., Manchester, VT 05255
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~21.95 miles west of Chester
  • 3 star hotel
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From$80
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Econo Lodge 2187 Depot St., Manchester, VT 05255
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~22.04 miles west of Chester
  • Cheap property
  • Check in time: 11:00
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From$60
Very Good 4.0 /5 Recent Reviews Call BookMore Details
The Olympia Lodge : 7259 Main St. 7259 Main St., Manchester Center, VT 05255
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~22.20 miles west of Chester
  • 3-star Mountain property
  • Check-in time: 2PM
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From$125
Very Good 4.0 /5 Latest Reviews Call BookMore Details
The Chalet Motel : 1875 Depot St. 1875 Depot St., Manchester Center, VT 05255
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~22.31 miles west of Chester
  • Low Cost Resort property
  • Check-in time: 3:00 pm
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
The Manchester View in Manchester Center Rte 7a North Po Box 1268, Manchester Center, VT 5255
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~22.39 miles west of Chester
  • Mid-scale hotel
  • Check in time: 15:00
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From$90
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Aspen at Manchester 5669 Main St., Manchester, VT 05255
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~23.30 miles west of Chester
  • 3 star Rural property
  • Check in time: 4:00PM
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Palmer House Resort Ascend Hotel Collection : 5383 Main St. 5383 Main St., Manchester Center, VT 05255 Website
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~23.47 miles west of Chester
  • 3-star Resort hotel
  • Check in time: 3pm
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From$100
Average 3.0 /5 Recent Reviews Call BookMore Details
On The River Inn Woodstock - Woodstock 1653 West Woodstock Rd., Woodstock, VT 05091
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~24.03 miles north of Chester
  • 4-star Mountain hotel
  • Gym is available on property
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From$125
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Manchester in Manchester 4519 Main St., Manchester, VT 05255
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~24.26 miles west of Chester
  • Midscale hotel
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From$99
Very Good 4.0 /5 Latest Reviews Call BookMore Details
The Inn at Mount Snow 401 Route 100, West Dover, VT 05356
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~24.81 miles southwest of Chester
  • Mid-scale Mountain hotel
  • Check in time: 3:00 PM
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From$99
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Kimpton Taconic Hotel in Manchester Village 3835 Main St., Manchester Village, VT 05254
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~24.82 miles west of Chester
  • Four-star Rural hotel
  • Check-in: 4:00 PM
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From$129
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Snow Lake Lodge Route 100 Po Box 2810, West Dover, VT 05356
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~24.95 miles southwest of Chester
  • Low-priced Resort hotel
  • Hotel has 4 floors
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From$79
Average 3.5 /5 Recent Reviews Call BookMore Details
The Equinox Golf Resort & Spa - Manchester 3567b Main St. Route 7a, Manchester, VT 05254
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~24.95 miles west of Chester
  • Four-star Mountain property
  • 12 suites in hotel
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From$119
Average 3.0 /5 Review Score Call BookMore Details
The Equinox Golf Resort & Spa - Manchester 3567 Main St. Route 7a, Manchester, VT 05254
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~24.96 miles west of Chester
  • 4-star Mountain hotel
  • 14 suites in property
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From$399
Average 3.0 /5 Review Score Call BookMore Details
Woodstock Inn & Resort Fourteen The Green, Woodstock, VT 05091
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~25.16 miles north of Chester
  • Expensive Resort hotel
  • 10 suites in hotel
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From$99
Very Good 4.0 /5 Recent Reviews Call BookMore Details
The Mountaineer Inn at Mt. Snow in Dover 401 Vermont Rte 100, Dover, VT 05356
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~25.20 miles southwest of Chester
  • Cheap property
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From$60
Average 3.0 /5 Read Reviews Call BookMore Details
Grand Summit Hotel 89 Mountain Rd., West Dover, VT 05356
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~25.39 miles southwest of Chester
  • Midscale Resort property
  • Hotel has 16 meeting rooms
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From$129
Very Good 4.0 /5 Review Score Call BookMore Details
Mount Snow Lodging in West Dover 89 Grand Summit Way, West Dover, VT 05356
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~25.41 miles southwest of Chester
  • 3-star property
  • 79 rooms in hotel
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From$90
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Grand Summit Resort - West Dover 21 Grand Summit Way, West Dover, VT 05356
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~25.41 miles southwest of Chester
  • Midscale hotel
  • 261 sleeping rooms in hotel
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From$90
Average 3.0 /5 Review Score Call BookMore Details
The Shire Hotel - Woodstock 46 Pleasant St., Woodstock, VT 05091
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~25.49 miles north of Chester
  • 4 star Mountain hotel
  • 50 rooms in hotel
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From$125
Average 3.0 /5 Guest Reviews Call BookMore Details
Hideaway Inn Mt. Snow - Dover 270 Handle Rd., Dover, VT 05356
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~25.50 miles southwest of Chester
  • 2 star Mountain property
  • 26 rooms in hotel
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From$50
Average 3.0 /5 Latest Reviews Call BookMore Details
Hampton Inn Brattleboro : 1378 Putney Rd. 1378 Putney Rd., Brattleboro, VT 05301
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~25.68 miles south of Chester
  • 3-star Rural hotel
  • Fitness center on property
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From$105
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Quality Inn & Conference Center Brattleboro North 1380 Putney Rd., Brattleboro, VT 05301
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~25.73 miles south of Chester
  • Midscale Mountain property
  • Fitness + Health Center
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From$80
Average 3.0 /5 Reviews Call BookMore Details
Layla's Riverside Lodge - West Dover 145 Route 100, West Dover, VT 05356
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~25.84 miles southwest of Chester
  • High end property
  • 2 floors in property
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From$219
Excellent 5.0 /5 Guest Reviews Call BookMore Details
Travelodge by Wyndham Brattleboro VT 1254 Putney Rd., Brattleboro, VT 05301
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~25.92 miles south of Chester
  • Cheap hotel
  • 2 floors in property
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From$60
Average 3.0 /5 Hotel Reviews Call BookMore Details
Comfort Inn & Suites Brattleboro I 91 - Brattleboro 1186 Putney Rd., Brattleboro, VT 05301 Website
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~26.00 miles south of Chester
  • Economical Highway property
  • Hotel has 15 suites
More Photos Image of Comfort Inn & Suites Brattleboro I 91
From$79
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Dexter's Inn 258 Stagecoach Rd., Sunapee, NH 03782
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~26.12 miles east of Chester
  • Affordable Mountain hotel
  • Check-in time: 3:00 pm
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From$100
Very Good 4.0 /5 Read Reviews Call BookMore Details
Riverside Hotel, an Ascend Collection Hotel : 20 Riverside Dr. 20 Riverside Dr., West Chesterfield, NH 03466
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~26.26 miles south of Chester
  • 3-star Riverfront property
  • Hotel has 3 floors
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From$129
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Black Mountain Inn in Brattleboro 959 Putney Rd., Brattleboro, VT 05301
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~26.48 miles south of Chester
  • Two star Suburban property
  • Has environment-friendly policy See more
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From$57
Average 3.5 /5 Read Reviews Call BookMore Details
Holiday Inn Express & Suites Brattleboro in Brattleboro 100 Chickering Dr., Brattleboro, VT 05301
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~26.53 miles south of Chester
  • Mid-scale Suburban property
  • 86 sleeping rooms in hotel
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From$79
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Colonial Motel And Spa in Brattleboro 889 Putney Rd., Brattleboro, VT 05301
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~26.57 miles south of Chester
  • 3 star Rural hotel
  • 5 suites in hotel
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From$59
Average 3.0 /5 Recent Reviews Call BookMore Details
Killington Grand Resort Hotel in Killington 228 East Mountain Rd., Killington, VT 05751
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~27.09 miles northwest of Chester
  • 3-star Resort property
  • Fitness + Health Center
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From$149
Very Good 4.0 /5 Reviews Call BookMore Details
Hideaway Inn Mt. Sunapee in Newbury 1403 New Hampshire Rte 103, Newbury, NH 03255
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~27.16 miles east of Chester
  • Mid-scale Resort property
  • 2 meeting rooms in hotel
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From$80
Average 3.0 /5 Reviews Call BookMore Details
Sunapee Harbor Cottages 4 Lake Ave., Sunapee, NH 03782
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~27.22 miles east of Chester
  • Four star hotel
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From$250
Very Good 4.0 /5 Read Reviews Call BookMore Details

Next: See My Chester Hotels with Pricing

Graph: Upcoming 20 Days of Chester Hotel Rates

Rates shown are nightly rates before taxes and do not necessarily reflect all Chester, VT discounts available. The chart reflects the cheapest Chester hotel for each day and each star rating category.

FAQs about hotels in Chester

What are the best rated hotels in Chester?

Layla's Riverside Lodge, Blue Gentian Lodge at Magic Mountain and Windham Hill Inn are the best rated hotels based on customer reviews in the last 365 days.

What are the most up-scale hotels in Chester?

Harvest Barn Inn, Grafton Inn and Windham Hill Inn are the top 3 luxury hotels near Chester city center.

What hotels are closest to the city center of Chester?

Grafton Inn, Best Western Springfield Hotel, and Castle Hill Resort And Spa are the properties closest to Chester city center.

What are the best independent hotels in Chester?

Layla's Riverside Lodge, Blue Gentian Lodge at Magic Mountain and Windham Hill Inn are the best rated independent hotels (not part of a big brand).

What are the best Choice Hotels branded hotels in Chester?

Econo Lodge, Comfort Inn & Suites Brattleboro I 91 and Riverside Hotel, an Ascend Collection Hotel are the best rated Choice Hotels branded hotels (based on HotelPlanner reviews score).

What are the most popular IHG hotels in Chester?

Kimpton Taconic Hotel, Holiday Inn Club Vacations Ascutney Mountain Resort and Holiday Inn Express & Suites Brattleboro are the best rated Intercontinental Hotel Group (IHG) branded hotels (based on user reviews score).

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