Search Villas in Winchester

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Property entrance
The Covered Bridge Inn

The Covered Bridge Inn

2.5 star property
7.6 out of 10, Good, (1001)
"Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests."
United States
Zachery
The price is SAR 297
SAR 327 total
includes taxes & fees
13 Dec - 14 Dec
The Covered Bridge Inn
Exterior
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (738)
"Staff was friendly and pool was nice"
United States
Joshua
The price is SAR 497
SAR 546 total
includes taxes & fees
22 Dec - 23 Dec
Comfort Inn & Suites Brattleboro I-91
Exterior
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 star property
8.4 out of 10, Very Good, (959)
"Enjoyed the breakfast options and the very comfortable bed. "
Canada
Nancy
The price is SAR 409
SAR 443 total
includes taxes & fees
29 Dec - 30 Dec
Keene Elm City Hotel, an Ascend Collection Hotel
Front of property
Blooming Inn

Guesthouse in Shelburne Falls

3.0 star property
9.2 out of 10, Wonderful, (124)
"Excellent! Really fun space with beautiful objects all around you. One of a kind, well run, seamless experience. "
United States
Ben
The price is SAR 246
SAR 458 total
includes taxes & fees
10 Dec - 11 Dec
Blooming Inn
Exterior
The Inn At Crumpin Fox

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (343)
"Room was great, we will be back again, favorite place in the valley thus far to stay. "
United States
Christine
The price is SAR 490
SAR 547 total
includes taxes & fees
22 Dec - 23 Dec
The Inn At Crumpin Fox
Exterior
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (352)
"Clean comfy nice staff "
United States
Katherine
The price is SAR 552
SAR 599 total
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn & Suites Keene
Exterior
The Putney Inn

Motel in Putney

2.5 star property
8.4 out of 10, Very Good, (1003)
"Nice motel. "
United States
Richard
The Putney Inn
Front of property
The Colonial Hotel

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1005)
"The perfect hotel!"
United States
Elizabeth
The Colonial Hotel
Front of property
Four Columns Inn

Bed & Breakfast in Newfane

4.0 star property
9.8 out of 10, Exceptional, (14)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
Property amenity
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very Good, (1000)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is SAR 522
SAR 566 total
includes taxes & fees
10 Dec - 11 Dec
Best Western Plus Keene Hotel
Exterior
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (877)
"Friendly staff, great breakfast, comfy beds"
United States
Lori
The price is SAR 688
SAR 768 total
includes taxes & fees
17 Dec - 18 Dec
Hampton Inn & Suites Greenfield
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (755)
"Front desk pleasant and helpful Breakfast was good Room was spacious and clean Able to walk to shopping and dining. "
United States
Stephen
The price is SAR 676
SAR 733 total
includes taxes & fees
1 Jan - 2 January 2026
Fairfield Inn & Suites by Marriott Keene Downtown
Front of property
The Carriage Barn Inn

Bed & Breakfast in Keene

3.0 star property
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is SAR 526
SAR 571 total
includes taxes & fees
29 Dec - 30 Dec
The Carriage Barn Inn
Sundeck
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
9.6 out of 10, Exceptional, (628)
"Clean room, beautiful location"
United States
Marcie
The price is SAR 571
SAR 620 total
includes taxes & fees
7 Jan - 8 January 2026
Riverside Hotel, an Ascend Collection Hotel
Front of property
Black Mountain Inn

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (474)
"Clean, very friendly staff. Will stay again."
United States
Scot
The price is SAR 338
SAR 372 total
includes taxes & fees
10 Dec - 11 Dec
Black Mountain Inn
Exterior
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2.0 star property
7.0 out of 10, Good, (1001)
"Not exactly spotless by the experience was better than at the Courtyard by Marriott on Railroad St. in Keene NH."
United States
Miroslaw
The price is SAR 306
SAR 332 total
includes taxes & fees
18 Dec - 19 Dec
Days Inn by Wyndham Keene NH
Front of property
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (435)
"Super cute place! Would stay here again"
United States
Danielle
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Exterior
The Burrell House

Guesthouse in Keene

2.5 star property
9.6 out of 10, Exceptional, (155)
"Very helpful, kind staff"
United States
Paitris
The Burrell House
Exterior
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
8.8 out of 10, Excellent, (1000)
"Very clean room, gentlemen at the front desk were welcoming and professional and the coffee was amazing! We are frequent visitors with you; we love IHG hotels. "
United States
Belinda
The price is SAR 540
SAR 595 total
includes taxes & fees
11 Dec - 12 Dec
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Property grounds
In town, newly remodeled studio with private balcony

Guesthouse in Shelburne Falls

10.0 out of 10, Exceptional, (119)
"We had a great visit! Easy to access, clean and comfortable. The studio had everything we needed!Great host!"
United States
Marina G.
The price is SAR 357
SAR 587 total
includes taxes & fees
10 Dec - 11 Dec
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

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Clean, courteous. "
Suzanne 1-night trip
Posted 17 hours ago
The Colonial Hotel