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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 in Grafton 92 Main St., Grafton, VT 05146
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~6.25 miles south of Chester
  • High end hotel
  • Hotel has 9 suites
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From$192 total
Very Good 4.0 /5 Reviews Call BookMore Details
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Best Western Springfield Hotel in Springfield 818 Charlestown Rd., Springfield, VT 05156
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~8.01 miles east of Chester
  • Mid-scale Highway hotel
  • Fitness + Health Center
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From$127 total
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
  • 3-star property
  • Check in time: 15:00
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From$108 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Pointe at Castle Hill Resort in Proctorsville 2940 State Route 103, Proctorsville, VT 05153
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~8.75 miles north of Chester
  • Midscale Rural property
  • 2 floors in hotel
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From$102 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Rodeway Inn Bellows Falls 593 Rockingham Rd., Bellows Falls, VT 05101
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~9.58 miles southeast of Chester
  • Cheap Mountain hotel
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From$72 total
Average 3.0 /5 Read Reviews Call BookMore Details
Blue Gentian Lodge at Magic Mountain : 289 Magic Mountain Access 289 Magic Mountain Access, Londonderry, VT 05148
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~9.78 miles west of Chester
  • Affordable Mountain property
  • Free breakfast
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From$142 total
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Harvest Barn Inn 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$132 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Okemo Mountain Lodging 77 Okemo Ridge Rd., Ludlow, NY 05149
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~11.34 miles northwest of Chester
  • 3-star property
  • Check-in time: 0:00
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From$108 total
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
  • Mid-scale property
  • 36 sleeping rooms in hotel
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From$108 total
Average 3.0 /5 Review Score Call BookMore Details
Solitude Village at Okemo by Vail Resorts : Solitude Rd. Solitude Rd., Ludlow, 05149
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~12.50 miles northwest of Chester
  • Affordable property
  • Hotel has 13 rooms
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From$108 total
Very Good 4.0 /5 Review Score Call BookMore Details
Windham Hill Inn : 311 Lawrence Dr. 311 Lawrence Dr., West Townshend, VT 05359
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~12.57 miles southwest of Chester
  • Expensive hotel
  • Check in: 14:00
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From$192 total
Very Good 4.5 /5 Read 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
  • Mid-scale property
  • 286 rooms in hotel
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From$108 total
Very Good 4.0 /5 Reviews Call BookMore Details
Royal Inn Claremont - Claremont 24 Sullivan St., Claremont, NH 03743
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~14.92 miles northeast of Chester
  • Economical hotel
  • Check-in time: 11:00
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From$78 total
Average 3.0 /5 Read 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
  • Mid-scale Mountain property
  • Hotel has an eco-friendly policy See policy
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From$144 total
Very Good 4.0 /5 Review Score Call BookMore Details
Wiley Inn in Peru 2759 Route 11, Peru, VT 05152
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~16.14 miles west of Chester
  • Three Star Mountain hotel
  • Comp. Breakfast
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From$70 total
Poor 2.0 /5 Hotel 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
  • Four-star Resort property
  • 4 rooms in hotel
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From$102 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
The Inn at Willow Pond in Manchester 74 Willow Pond Rd., Manchester, VT 05255
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~21.95 miles west of Chester
  • 3 star property
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From$96 total
Very Good 4.0 /5 Reviews Call BookMore Details
Econo Lodge : 2187 Depot St. 2187 Depot St., Manchester, VT 05255
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~22.04 miles west of Chester
  • Two star property
  • Free breakfast available
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From$72 total
Very Good 4.0 /5 Guest 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
  • Hotel has an eco-friendly policy Read more
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From$150 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
The Chalet Motel in Manchester Center 1875 Depot St., Manchester Center, VT 05255
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~22.31 miles west of Chester
  • Cheap Resort property
  • Hotel has 32 rooms
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From$96 total
Average 3.0 /5 Read 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
  • 3 star property
  • 36 rooms in property
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From$108 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Aspen at Manchester : 5669 Main St. 5669 Main St., Manchester, VT 05255
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~23.30 miles west of Chester
  • Affordable Rural hotel
  • Check-in time: 4:00PM
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From$96 total
Average 3.0 /5 Reviews Call BookMore Details
Palmer House Resort Ascend Hotel Collection in Manchester Center 5383 Main St., Manchester Center, VT 05255 Website
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~23.47 miles west of Chester
  • Three Star Resort property
  • Check in: 3pm
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From$120 total
Average 3.0 /5 Reviews Call BookMore Details
On The River Inn Woodstock in Woodstock 1653 West Woodstock Rd., Woodstock, VT 05091
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~24.03 miles north of Chester
  • Four-star Mountain hotel
  • 3 floors in hotel
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From$150 total
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn & Suites Manchester - Manchester 4519 Main St., Manchester, VT 05255
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~24.26 miles west of Chester
  • Mid-scale property
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From$118 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
The Inn at Mount Snow - West Dover 401 Route 100, West Dover, VT 05356
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~24.81 miles southwest of Chester
  • Affordable Mountain hotel
  • Hotel has 14 rooms
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From$118 total
Very Good 4.0 /5 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
  • Expensive Rural property
  • 86 sleeping rooms in hotel
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From$154 total
Very Good 4.5 /5 Latest Reviews Call BookMore Details
Snow Lake Lodge - West Dover 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 13 suites
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From$94 total
Average 3.5 /5 Read Reviews Call BookMore Details
The Equinox Golf Resort & Spa in Manchester 3567b Main St. Route 7a, Manchester, VT 05254
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~24.95 miles west of Chester
  • High-end Mountain hotel
  • 12 suites in property
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From$142 total
Average 3.0 /5 Read Reviews Call BookMore Details
The Equinox Golf Resort & Spa in Manchester 3567 Main St. Route 7a, Manchester, VT 05254
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~24.96 miles west of Chester
  • High end Mountain property
  • Hotel has 195 rooms
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From$478 total
Average 3.0 /5 Review Score Call BookMore Details
Woodstock Inn & Resort - Woodstock Fourteen The Green, Woodstock, VT 05091
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~25.16 miles north of Chester
  • 4-star Resort hotel
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From$118 total
Very Good 4.0 /5 Read Reviews Call BookMore Details
The Mountaineer Inn at Mt. Snow 401 Vermont Rte 100, Dover, VT 05356
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~25.20 miles southwest of Chester
  • 2-star hotel
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From$72 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Grand Summit Hotel : 89 Mountain Rd. 89 Mountain Rd., West Dover, VT 05356
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~25.39 miles southwest of Chester
  • Three Star Resort hotel
  • Hotel has 16 meeting rooms
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From$154 total
Very Good 4.0 /5 Review Score Call BookMore Details
Mount Snow Lodging 89 Grand Summit Way, West Dover, VT 05356
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~25.41 miles southwest of Chester
  • 3 star hotel
  • 79 rooms in property
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From$108 total
Very Good 4.0 /5 Recent 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
  • Mid-scale hotel
  • 261 rooms in property
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From$108 total
Average 3.0 /5 Review Score Call BookMore Details
The Shire Hotel : 46 Pleasant St. 46 Pleasant St., Woodstock, VT 05091
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~25.49 miles north of Chester
  • High end Mountain property
  • Hotel has 3 floors
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From$150 total
Average 3.0 /5 Reviews Call BookMore Details
Hideaway Inn Mt. Snow : 270 Handle Rd. 270 Handle Rd., Dover, VT 05356
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~25.50 miles southwest of Chester
  • Inexpensive Mountain property
  • 26 sleeping rooms in hotel
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From$60 total
Average 3.0 /5 Read Reviews Call BookMore Details
Hampton Inn Brattleboro in Brattleboro 1378 Putney Rd., Brattleboro, VT 05301
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~25.68 miles south of Chester
  • 3 star Rural property
  • 12 suites in property
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From$126 total
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
  • Mid-scale Mountain hotel
  • Hotel has 98 rooms
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From$96 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Layla's Riverside Lodge in West Dover 145 Route 100, West Dover, VT 05356
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~25.84 miles southwest of Chester
  • Four-star property
  • Check in: 15:00
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From$262 total
Excellent 5.0 /5 Hotel Reviews Call BookMore Details
Travelodge by Wyndham Brattleboro VT - Brattleboro 1254 Putney Rd., Brattleboro, VT 05301
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~25.92 miles south of Chester
  • Low-priced hotel
  • Hotel has 59 rooms
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From$72 total
Average 3.0 /5 Review Score 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
  • Low-priced Highway hotel
  • 4 floors in hotel
More Photos Exterior of Comfort Inn & Suites Brattleboro I 91
From$94 total
Very Good 4.0 /5 Reviews Call BookMore Details
Dexter's Inn 258 Stagecoach Rd., Sunapee, NH 03782
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~26.12 miles east of Chester
  • 3-star Mountain property
  • Hotel has 17 rooms
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From$120 total
Very Good 4.0 /5 Read Reviews Call BookMore Details
Riverside Hotel, an Ascend Collection Hotel in West Chesterfield 20 Riverside Dr., West Chesterfield, NH 03466
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~26.26 miles south of Chester
  • 3-star Riverfront property
  • Fitness + Health Center
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From$154 total
Very Good 4.0 /5 Reviews Call BookMore Details
Black Mountain Inn - Brattleboro 959 Putney Rd., Brattleboro, VT 05301
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~26.48 miles south of Chester
  • 2 star Suburban hotel
  • 40 rooms in property
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From$68 total
Average 3.5 /5 Latest Reviews Call BookMore Details
Holiday Inn Express & Suites Brattleboro : 100 Chickering Dr. 100 Chickering Dr., Brattleboro, VT 05301
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~26.53 miles south of Chester
  • Three Star Suburban property
  • Has environment-friendly policy Learn more
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From$94 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Colonial Motel - Brattleboro 889 Putney Rd., Brattleboro, VT 05301
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~26.57 miles south of Chester
  • Affordable Rural property
  • Hotel has 2 floors
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From$70 total
Average 3.0 /5 Latest Reviews Call BookMore Details
Killington Grand Resort Hotel : 228 East Mountain Rd. 228 East Mountain Rd., Killington, VT 05751
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~27.09 miles northwest of Chester
  • Three Star Resort hotel
  • Check-in: 4:00 PM
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From$178 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hideaway Inn Mt. Sunapee 1403 New Hampshire Rte 103, Newbury, NH 03255
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~27.16 miles east of Chester
  • Three Star Resort property
  • Check-in: 3:00 PM
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From$96 total
Average 3.0 /5 Review Score Call BookMore Details
Sunapee Harbor Cottages 4 Lake Ave., Sunapee, NH 03782
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~27.22 miles east of Chester
  • High end hotel
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From$300 total
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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