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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/Accommodations

Grafton Inn : 92 Main St.
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
92 Main St., Grafton, VT 05146 ~6.26 miles south of Chester
  • High-end hotel
  • Hotel has 45 rooms
More Photos Exterior of Grafton Inn
From£117
Very good 4.0 /5 Hotel Reviews Call BookMore Details
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Best Western Springfield Hotel - Springfield
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
818 Charlestown Rd., Springfield, VT 05156 ~8.02 miles east of Chester
  • Three Star Highway hotel
  • 88 rooms in property
More Photos Image of Best Western Springfield Hotel
From£77
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Castle Hill Resort And Spa in Ludlow
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
Junction Route 103 & Route 1, Ludlow, VT 05149 ~8.67 miles north of Chester
  • 3 star property
  • 20 rooms in hotel
More Photos Image of Castle Hill Resort And Spa
From£66
Very good 4.0 /5 Guest Reviews Call BookMore Details
Pointe at Castle Hill Resort - Proctorsville
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
2940 State Route 103, Proctorsville, VT 05153 ~8.77 miles north of Chester
  • 3-star Rural hotel
  • 2 floors in hotel
More Photos Photo of Pointe at Castle Hill Resort
From£62
Very good 4.0 /5 Latest Reviews Call BookMore Details
Rodeway Inn : 593 Rockingham Rd.
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
593 Rockingham Rd., Bellows Falls, VT 05101 ~9.60 miles southeast of Chester
  • Low Cost Mountain property
  • 27 rooms in hotel
More Photos Photo of Rodeway Inn
From£44
Average 3.0 /5 Read Reviews Call BookMore Details
Blue Gentian Lodge at Magic Mountain - Londonderry
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
289 Magic Mountain Access, Londonderry, VT 05148 ~9.80 miles west of Chester
  • Three Star Mountain hotel
  • 12 rooms in hotel
More Photos Photo of Blue Gentian Lodge at Magic Mountain
From£87
Very good 4.5 /5 Read Reviews Call BookMore Details
Harvest Barn Inn : 16 Webb Terrace
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
16 Webb Terrace, Bellows Falls, VT 05101 ~10.43 miles southeast of Chester
  • Luxurious Five Star property
More Photos hotel room
From£80
Very good 4.0 /5 Latest Reviews Call BookMore Details
Okemo Mountain Lodging : 77 Okemo Ridge Rd.
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
77 Okemo Ridge Rd., Ludlow, NY 05149 ~11.35 miles northwest of Chester
  • Midscale property
More Photos Exterior of Okemo Mountain Lodging
From£66
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Mountain Lodge at Okemo : 318 Mountain Rd.
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
318 Mountain Rd., Ludlow, NY 05149 ~11.39 miles northwest of Chester
  • Midscale property
  • 36 rooms in hotel
More Photos Photo of Mountain Lodge at Okemo
From£66
Average 3.0 /5 Review Score Call BookMore Details
Solitude Village at Okemo
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
Solitude Rd., Ludlow, 05149 ~12.51 miles northwest of Chester
  • Three Star hotel
  • Check in: 17:00
More Photos Photo of Solitude Village at Okemo
From£66
Very good 4.0 /5 Review Score Call BookMore Details
Windham Hill Inn : 311 Lawrence Dr.
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
311 Lawrence Dr., West Townshend, VT 05359 ~12.59 miles southwest of Chester
  • Four-star property
  • Check-in: 14:00
More Photos Photo of Windham Hill Inn
From£117
Very good 4.5 /5 Recent Reviews Call BookMore Details
Jackson Gore Village
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
111 Jackson Gore Rd., Ludlow, NY 05149 ~12.64 miles northwest of Chester
  • Three Star property
  • Check-in time: 17:00
More Photos Image of Jackson Gore Village
From£66
Very good 4.0 /5 Review Score Call BookMore Details
Royal Inn Claremont in Claremont
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
24 Sullivan St., Claremont, NH 03743 ~14.93 miles northeast of Chester
  • Cheap hotel
  • Complimentary breakfast is offered
More Photos Exterior of Royal Inn Claremont
From£47
Average 3.0 /5 Read Reviews Call BookMore Details
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Holiday Inn Club Vacations Ascutney Mountain Resort
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
485 Hotel Rd., Brownsville, VT 05037 ~15.25 miles northeast of Chester
  • Affordable Mountain property
  • 4 floors in property
More Photos Image of Holiday Inn Club Vacations Ascutney Mountain Resort
From£88
Very good 4.0 /5 Review Score Call BookMore Details
Wiley Inn
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
2759 Route 11, Peru, VT 05152 ~16.17 miles west of Chester
  • Midscale Mountain hotel
  • Free comp. breakfast
More Photos Image of Wiley Inn
From£43
Poor 2.0 /5 Latest Reviews Call BookMore Details
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Thoma House : 4216 Vt Rte 11
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
4216 Vt Rte 11, Peru, VT 05152 ~17.52 miles west of Chester
  • 4-star Resort hotel
  • Check-in: 5:00 PM
More Photos Photo of Thoma House
From£62
Very good 4.0 /5 Review Score Call BookMore Details
The Inn at Willow Pond - Manchester
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
74 Willow Pond Rd., Manchester, VT 05255 ~21.99 miles west of Chester
  • Midscale hotel
More Photos Photo of The Inn at Willow Pond
From£58
Very good 4.0 /5 Reviews Call BookMore Details
Econo Lodge : 2187 Depot St.
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
2187 Depot St., Manchester, VT 05255 ~22.09 miles west of Chester
  • Economical hotel
  • Check in time: 11:00
More Photos Photo of Econo Lodge
From£44
Very good 4.0 /5 Recent Reviews Call BookMore Details
The Olympia Lodge
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
7259 Main St., Manchester Center, VT 05255 ~22.25 miles west of Chester
  • Midscale Mountain hotel
  • Free comp. breakfast
More Photos Image of The Olympia Lodge
From£91
Very good 4.0 /5 Latest Reviews Call BookMore Details
The Chalet Motel
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
1875 Depot St., Manchester Center, VT 05255 ~22.36 miles west of Chester
  • 2 star Resort property
  • 32 rooms in property
More Photos Exterior of The Chalet Motel
From£58
Average 3.0 /5 Latest Reviews Call BookMore Details
The Manchester View
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
Rte 7a North Po Box 1268, Manchester Center, VT 5255 ~22.44 miles west of Chester
  • Affordable property
  • Hotel has 2 floors
More Photos Image of The Manchester View
From£66
Very good 4.0 /5 Guest Reviews Call BookMore Details
Aspen at Manchester
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
5669 Main St., Manchester, VT 05255 ~23.35 miles west of Chester
  • 3 star Rural hotel
  • 7 suites in property
More Photos Image of Aspen at Manchester
From£58
Average 3.0 /5 Reviews Call BookMore Details
Palmer House Resort Ascend Hotel Collection : 5383 Main St.
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
5383 Main St., Manchester Center, VT 05255 Website ~23.52 miles west of Chester
  • Affordable Resort property
  • 50 sleeping rooms in hotel
More Photos Image of Palmer House Resort Ascend Hotel Collection
From£73
Average 3.0 /5 Reviews Call BookMore Details
On The River Inn Woodstock
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
1653 West Woodstock Rd., Woodstock, VT 05091 ~24.06 miles north of Chester
  • Expensive Mountain hotel
  • 3 floors in property
More Photos Exterior of On The River Inn Woodstock
From£91
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Manchester
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
4519 Main St., Manchester, VT 05255 ~24.31 miles west of Chester
  • Midscale hotel
More Photos Exterior of Hampton Inn & Suites Manchester
From£72
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Four Points by Sheraton Hotel & Suites Calgary West
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
3835 Main St., Manchester Village, VT 05254 ~24.86 miles west of Chester
  • Four-star Rural hotel
  • 7 suites in property
More Photos Photo of Four Points by Sheraton Hotel & Suites Calgary West
From£189
Very good 4.0 /5 Hotel Reviews Call BookMore Details
The Inn at Mount Snow - West Dover
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
401 Route 100, West Dover, VT 05356 ~24.87 miles southwest of Chester
  • 3 star Mountain hotel
  • 2 conference rooms in property
More Photos Exterior of The Inn at Mount Snow
From£72
Very good 4.0 /5 Read Reviews Call BookMore Details
Snow Lake Lodge in West Dover
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
Route 100 Po Box 2810, West Dover, VT 05356 ~25.01 miles southwest of Chester
  • Low-priced Resort property
  • Hotel has 13 suites
More Photos Photo of Snow Lake Lodge
From£57
Average 3.5 /5 Reviews Call BookMore Details
The Equinox Golf Resort & Spa
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
3567b Main St. Route 7a, Manchester, VT 05254 ~25.01 miles west of Chester
  • High-end Mountain property
  • Access to gym on-site
More Photos Image of The Equinox Golf Resort & Spa
From£87
Average 3.0 /5 Guest Reviews Call BookMore Details
The Equinox Golf Resort & Spa
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
3567 Main St. Route 7a, Manchester, VT 05254 ~25.01 miles west of Chester
  • Four star Mountain hotel
  • Fitness center on property
More Photos Image of The Equinox Golf Resort & Spa
From£292
Average 3.0 /5 Latest Reviews Call BookMore Details
Woodstock Inn & Resort
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
Fourteen The Green, Woodstock, VT 05091 ~25.20 miles north of Chester
  • 4-star Resort property
More Photos Image of Woodstock Inn & Resort
From£72
Very good 4.0 /5 Read Reviews Call BookMore Details
The Mountaineer Inn at Mt. Snow in Dover
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
401 Vermont Rte 100, Dover, VT 05356 ~25.26 miles southwest of Chester
  • 2 star property
More Photos hotel room
From£44
Average 3.0 /5 Read Reviews Call BookMore Details
Grand Summit Hotel in West Dover
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
89 Mountain Rd., West Dover, VT 05356 ~25.44 miles southwest of Chester
  • Mid-scale Resort property
  • Hotel has 16 meeting rooms
More Photos Exterior of Grand Summit Hotel
From£94
Very good 4.0 /5 Guest Reviews Call BookMore Details
Mount Snow Lodging
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
89 Grand Summit Way, West Dover, VT 05356 ~25.47 miles southwest of Chester
  • 3 star property
  • Check-in: 18:00
More Photos hotel room
From£66
Very good 4.0 /5 Guest Reviews Call BookMore Details
Grand Summit Resort : 21 Grand Summit Way
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
21 Grand Summit Way, West Dover, VT 05356 ~25.47 miles southwest of Chester
  • Affordable hotel
  • Check-in time: 18:00
More Photos hotel room
From£66
Average 3.0 /5 Review Score Call BookMore Details
The Shire Hotel - Woodstock
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
46 Pleasant St., Woodstock, VT 05091 ~25.53 miles north of Chester
  • High end Mountain property
  • Check in time: 15:00
More Photos hotel room
From£91
Average 3.0 /5 Reviews Call BookMore Details
Mountaineer Inn : 270 Handle Rd.
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
270 Handle Rd., Dover, VT 05356 ~25.56 miles southwest of Chester
  • Economical Mountain hotel
  • 2 meeting rooms in hotel
More Photos Image of Mountaineer Inn
From£36
Average 3.0 /5 Read Reviews Call BookMore Details
Hampton Inn Brattleboro in Brattleboro
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
1378 Putney Rd., Brattleboro, VT 05301 ~25.71 miles south of Chester
  • 3-star Rural property
  • Hotel has 12 suites
More Photos Exterior of Hampton Inn Brattleboro
From£77
Very good 4.0 /5 Latest Reviews Call BookMore Details
Quality Inn & Conference Center : 1380 Putney Rd.
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
1380 Putney Rd., Brattleboro, VT 05301 ~25.77 miles south of Chester
  • Mid-scale Mountain hotel
  • Gym is available on property
More Photos Image of Quality Inn & Conference Center
From£58
Average 3.0 /5 Read Reviews Call BookMore Details
Layla's Riverside Lodge - West Dover
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
145 Route 100, West Dover, VT 05356 ~25.89 miles southwest of Chester
  • Four-star hotel
  • 15 rooms in hotel
More Photos Exterior of Layla's Riverside Lodge
From£160
Excellent 5.0 /5 Hotel Reviews Call BookMore Details
Travelodge by Wyndham Brattleboro VT
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
1254 Putney Rd., Brattleboro, VT 05301 ~25.96 miles south of Chester
  • Economy hotel
  • Hotel has 59 rooms
More Photos Exterior of Travelodge by Wyndham Brattleboro VT
From£44
Average 3.0 /5 Reviews Call BookMore Details
Comfort Inn & Suites Brattleboro I-91 - Brattleboro
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
1186 Putney Rd., Brattleboro, VT 05301 Website ~26.04 miles south of Chester
  • 2 star Highway hotel
  • 15 suites in hotel
More Photos Photo of Comfort Inn & Suites Brattleboro I-91
From£57
Very good 4.0 /5 Latest Reviews Call BookMore Details
Dexter's Inn
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
258 Stagecoach Rd., Sunapee, NH 03782 ~26.14 miles east of Chester
  • Midscale Mountain property
  • Hotel has 17 rooms
More Photos Image of Dexter's Inn
From£73
Very good 4.0 /5 Read Reviews Call BookMore Details
Riverside Hotel, Ascend Hotel Collection in West Chesterfield
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
20 Riverside Dr., West Chesterfield, NH 03466 ~26.30 miles south of Chester
  • Midscale Riverfront hotel
  • 34 rooms in hotel
More Photos Image of Riverside Hotel, Ascend Hotel Collection
From£94
Very good 4.0 /5 Guest Reviews Call BookMore Details
Black Mountain Inn in Brattleboro
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
959 Putney Rd., Brattleboro, VT 05301 ~26.52 miles south of Chester
  • Two-star Suburban property
  • Hotel has 2 floors
More Photos Photo of Black Mountain Inn
From£41
Average 3.5 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express & Suites Brattleboro
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
100 Chickering Dr., Brattleboro, VT 05301 ~26.57 miles south of Chester
  • Three Star Suburban property
  • Access to gym on-site
More Photos Exterior of Holiday Inn Express & Suites Brattleboro
From£57
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Colonial Motel And Spa - Brattleboro
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
889 Putney Rd., Brattleboro, VT 05301 ~26.61 miles south of Chester
  • Mid-scale Rural hotel
  • Complimentary breakfast is offered
More Photos Photo of Colonial Motel And Spa
From£43
Average 3.0 /5 Review Score Call BookMore Details
A Hotel Inn Sunapee
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
1403 New Hampshire Rte 103, Newbury, NH 03255 ~27.11 miles east of Chester
  • Inexpensive Resort hotel
  • Free complimentary breakfast
More Photos Photo of A Hotel Inn Sunapee
From£46
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Killington Grand Resort Hotel - Killington
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
228 East Mountain Rd., Killington, VT 05751 ~27.12 miles northwest of Chester
  • 3 star Resort hotel
  • 25 suites in hotel
More Photos Photo of Killington Grand Resort Hotel
From£109
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Sunapee Harbor Cottages
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
4 Lake Ave., Sunapee, NH 03782 ~27.24 miles east of Chester
  • Four-star hotel
More Photos hotel room
From£183
Very good 4.0 /5 Recent 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, Ascend Hotel Collection are the best rated Choice Hotels branded hotels (based on HotelPlanner reviews score).

What are the most popular IHG hotels in Chester?

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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