Search Guest Houses in Winchester from CA $99

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Winchester guest houses

A historic brick building with a porch and a sign reading "Burrell House."

1. The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (189 reviews)
"The Burrell House is a lovely historic home convenient to downtown Keene. The room was very clean and the bed super comfortable. There is no staff but it worked fine for my stay."
United States
Carol
The price is CA $176
CA $196 total
includes taxes & fees
Nov 16 - Nov 17
The Burrell House
A two-story house with a porch, a balcony, and a chimney.

2. Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (151 reviews)
"Like the ambiance as well as the decor! The location was perfect for walking around town!"
United States
Robert
The price is CA $99
CA $180 total
includes taxes & fees
Nov 8 - Nov 9
Blooming Inn
A two-story house with a stone staircase leading to a wooden front door.

3. The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.2 out of 10, Wonderful, (75 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 $273
CA $300 total
includes taxes & fees
Nov 8 - Nov 9
The Inn At Quail Run
A wooden deck with two black wicker chairs and a small round table with a white vase.

4. In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony
Shelburne Falls
10.0 out of 10, Exceptional, (136 reviews)
"Nice little studio in a pretty little town. Had a great stay."
United States
Apoorva
The price is CA $230
CA $322 total
includes taxes & fees
Nov 17 - Nov 18
In town, newly remodeled studio with private balcony
A wooden cabin with a red roof, a balcony, and a staircase leading to the upper level.

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, (22 reviews)
"The tree house was lovely! The directions should say, take a left at the church and include mileage (how far to the fork in the road, how far to the mailboxes). The setting offers places to walk and nearby hiking trails."
United States
Sara H.
The price is CA $315
CA $450 total
includes taxes & fees
Nov 15 - Nov 16
Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing
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.
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Learn more about Winchester

Hike the scenic trails of Pisgah State Park where rangers know which routes offer the best wildlife viewing. Explore the historic downtown district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

See all hotels in Winchester
A snow-covered bridge over a river with a red roof, surrounded by trees and buildings.

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