A snow-covered town with a river running through it, surrounded by mountains and trees.

Search Guest Houses in Winchester from CA $181

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Winchester guest houses

Exterior

1. The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (181 reviews)
"Wonderful stay"
United States
Justin
The price is CA $162
CA $181 total
includes taxes & fees
Sep 8 - Sep 9
The Burrell House
Front of property

2. Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (149 reviews)
"Lovely Victorian house on a quiet street. Only a few blocks from the center of the town of Shelburne Falls, which is a charming New England town with a lovely river and a beautiful "bridge of flowers.""
United States
steven
The price is CA $129
CA $212 total
includes taxes & fees
Sep 16 - Sep 17
Blooming Inn
Lobby sitting area

3. Inn at Valley Farms

Inn at Valley Farms
2.0 star property
Walpole
9.8 out of 10, Exceptional, (23 reviews)
"A classic New England B&B. Light on frills but absolutely comfortable."
United States
Ronald
The price is CA $282
CA $306 total
includes taxes & fees
Sep 7 - Sep 8
Inn at Valley Farms
Exterior

4. The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.2 out of 10, Wonderful, (74 reviews)
"For booking an overnight stay at the last minute, this place hit the jackpot, and BEYOND EXCEEDED my expectations! The owner was so sweet, and if I ever pass through Wilmington again, I'd definitely stay there again!!!"
United States
Chandra
The price is CA $284
CA $312 total
includes taxes & fees
Oct 1 - Oct 2
The Inn At Quail Run
Exterior

5. Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing

Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing
Munsonville
10.0 out of 10, Exceptional, (17 reviews)
"Great little place to stay. Minimal living style away from it all."
United States
Ryan W.
The price is CA $311
CA $467 total
includes taxes & fees
Sep 7 - Sep 8
Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing
Exterior

6. Cooper Hill Inn

Cooper Hill Inn
2.0 star property
West Dover
8.8 out of 10, Excellent, (8 reviews)
"Very convenient to Mount Snow and we loved the plentiful cozy places to sit and read or interact with other guests. The bed was comfortable, and the shared kitchen space was very well stocked and clean. We will definitely stay again!"
United States
Rosa
The price is CA $275
CA $302 total
includes taxes & fees
Oct 6 - Oct 7
Cooper Hill Inn
Property grounds

7. In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony
Shelburne Falls
10.0 out of 10, Exceptional, (131 reviews)
"It's a great place to stay! Bed is comfortable. Large room, nicely furnished. Would be glad to stay here again!"
United States
Jim E.
The price is CA $131
CA $216 total
includes taxes & fees
Oct 6 - Oct 7
In town, newly remodeled studio with private balcony
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Gardner Inn

Gardner Inn

8/10 Good
"It was clean and a nice hotel"
Sarah 1-night trip
Posted 2 hours ago
Gardner Inn

Find out more about Winchester

Winchester Guest Houses information

Number of reviews
560
Accommodation
9 Guest Houses
Lowest Price
CA $181
Highest Price
CA $467

Explore a world of travel with Expedia