Search Guest Houses in Chester
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 14 Guest Houses in Chester with updated reviews, rates, and availability.

Fullerton Inn
Fullerton Inn
8.0 out of 10, Very Good, (344)
The price is AED 474
AED 516 total
includes taxes & fees
12 Apr - 13 Apr

Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
9.2 out of 10, Wonderful, (89)
The price is AED 1,218
AED 1,327 total
includes taxes & fees
17 Apr - 18 Apr

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
8.0 out of 10, Very Good, (1)
The price is AED 312
AED 576 total
includes taxes & fees
6 Apr - 7 Apr

King & Queen Suite in Historic Inn Circa 1780
King & Queen Suite in Historic Inn Circa 1780
9.6 out of 10, Exceptional, (14)
The price is AED 327
AED 605 total
includes taxes & fees
7 Apr - 8 Apr

Honeymoon Suite with Jacuzzi Tub in Historic Inn
Honeymoon Suite with Jacuzzi Tub in Historic Inn
8.6 out of 10, Excellent, (7)
The price is AED 364
AED 613 total
includes taxes & fees
14 Apr - 15 Apr

Room in Historic Inn! 20 Minutes to Okemo!
Room in Historic Inn! 20 Minutes to Okemo!
9.4 out of 10, Exceptional, (13)
The price is AED 327
AED 572 total
includes taxes & fees
18 Apr - 19 Apr

1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!
9.6 out of 10, Exceptional, (36)

Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub
Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub
10.0 out of 10, Exceptional, (3)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Chester

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
10.0 out of 10, Exceptional, (23)

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
9.0 out of 10, Wonderful, (42)

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (204)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Chester hotels
Recent reviews of Chester hotels

The Manchester View
5/5 Excellent
"Staff nice and friendly"
A verified traveler from Windham stayed at The Manchester View
Posted 2 days ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
- Guest Houses in North Springfield
- Guest Houses in Grafton
- Guest Houses in Andover
- Guest Houses in Weston
- Guest Houses in West Townshend
- Guest Houses in Windham
- Guest Houses in Cavendish
- Guest Houses in Londonderry
- Guest Houses in Springfield
- Guest Houses in Rockingham
- Guest Houses in Bellows Falls
- Guest Houses in Perkinsville