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Dec 12 - Dec 14
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Condo Rentals in Winchester

No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Interior
The Colonial Hotel

The Colonial Hotel

3.0 star property
Gardner
8.8 out of 10, Excellent, (1000)
"Great hotel, fantastic restaurant, wonderful place!"
United States
Kate
$144 nightly
The price is $161
Dec 8 - Dec 9
Total with taxes and fees
The Colonial Hotel
Double Room | Free WiFi
Gardner Inn

Gardner Inn

2.0 star property
Gardner
5.6 out of 10, (16)
"The property needs work but hte staff was pleasant and the facility was quiet. "
United States
Lou
$89 nightly
The price is $100
Jan 4 - Jan 5, 2026
Total with taxes and fees
Gardner Inn
Breakfast area
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
Peterborough
9.4 out of 10, Exceptional, (433)
"Super cute place! Would stay here again"
United States
Danielle
$135 nightly
The price is $147
Dec 8 - Dec 9
Total with taxes and fees
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Exterior
Monadnock Inn

Monadnock Inn

2.5 star property
Jaffrey
7.6 out of 10, Good, (277)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
United States
Sharon-Ann C
$148 nightly
The price is $161
Dec 6 - Dec 7
Total with taxes and fees
Monadnock Inn
Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

3.0 star property
Keene
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
$132 nightly
The price is $144
Dec 29 - Dec 30
Total with taxes and fees
The Carriage Barn Inn
Reception
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3.0 star property
Keene
8.8 out of 10, Excellent, (1001)
"Lovely hotel"
United States
ronald
$161 nightly
The price is $174
Jan 2 - Jan 3, 2026
Total with taxes and fees
Courtyard by Marriott Keene Downtown
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
Keene
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
$161 nightly
The price is $174
Jan 2 - Jan 3, 2026
Total with taxes and fees
Fairfield Inn & Suites by Marriott Keene Downtown
Exterior
The Burrell House

The Burrell House

2.5 star property
Keene
9.6 out of 10, Exceptional, (155)
"Very helpful, kind staff"
United States
Paitris
$143 nightly
The price is $156
Dec 5 - Dec 6
Total with taxes and fees
The Burrell House
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3.0 star property
Keene
8.4 out of 10, Very Good, (1000)
"Great staff, clean room, nice breakfast"
United States
DORTHY
$139 nightly
The price is $151
Dec 7 - Dec 8
Total with taxes and fees
Best Western Plus Keene Hotel
Reception
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 star property
Keene
8.8 out of 10, Excellent, (351)
"Nice place to stay, nice area, will stay again."
United States
Catherine
$147 nightly
The price is $160
Dec 23 - Dec 24
Total with taxes and fees
Hampton Inn & Suites Keene
Indoor pool
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 star property
Keene
8.4 out of 10, Very Good, (957)
"Enjoyed the breakfast options and the very comfortable bed. "
Canada
Nancy
$109 nightly
The price is $118
Dec 25 - Dec 26
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel
In-room safe, desk, blackout drapes, iron/ironing board
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2.0 star property
Keene
7.0 out of 10, Good, (1006)
"Very professional people good service good staff "
United States
George
$92 nightly
The price is $100
Dec 21 - Dec 22
Total with taxes and fees
Days Inn by Wyndham Keene NH
Free daily full breakfast
Centennial House

Centennial House

3.5 star property
Northfield
9.6 out of 10, Exceptional, (173)
"The house was cozy and inviting. Felt the history all around me and the breakfast made and served by Joan was great. We recommend this place for those looking for that historical b&b experience. "
United States
Paul
$201 nightly
The price is $213
Dec 30 - Dec 31
Total with taxes and fees
Centennial House
Library
Inn at Valley Farms

Inn at Valley Farms

2.0 star property
Walpole
10.0 out of 10, Exceptional, (13)
"Picturesque, family run bed and breakfast."
United States
Jay
$147 nightly
The price is $160
Dec 7 - Dec 8
Total with taxes and fees
Inn at Valley Farms
Front of property
The Inn At Crumpin Fox

The Inn At Crumpin Fox

2.5 star property
Bernardston
9.2 out of 10, Wonderful, (342)
"Room was great, we will be back again, favorite place in the valley thus far to stay. "
United States
Christine
$145 nightly
The price is $162
Dec 7 - Dec 8
Total with taxes and fees
The Inn At Crumpin Fox
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
$301 nightly
The price is $327
Dec 7 - Dec 8
Total with taxes and fees
Chesterfield Inn
Room, 2 Queen Beds, Non Smoking | Down comforters, desk, blackout drapes, soundproofing
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 star property
Greenfield
8.6 out of 10, Excellent, (876)
"Friendly staff, great breakfast, comfy beds"
United States
Lori
$183 nightly
The price is $205
Dec 10 - Dec 11
Total with taxes and fees
Hampton Inn & Suites Greenfield
Exterior
The Putney Inn

The Putney Inn

2.5 star property
Putney
8.4 out of 10, Very Good, (1000)
"Nice motel. "
United States
Richard
$79 nightly
The price is $87
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Putney Inn
Hiking
Latchis Hotel

Latchis Hotel

2.5 star property
Brattleboro
8.4 out of 10, Very Good, (834)
"Great stay"
United States
Jason
$125 nightly
The price is $138
Dec 10 - Dec 11
Total with taxes and fees
Latchis Hotel
Exterior
The One Cat B&B

The One Cat B&B

2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
$241 nightly
The price is $266
Dec 9 - Dec 10
Total with taxes and fees
The One Cat B&B
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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Top Winchester Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"The customer service at this hotel is consistently exceptional. Every staff member is friendly, professional, and welcoming, creating an atmosphere that feels truly comfortable. The property is impeccably clean, and the breakfast offerings are always enjoyable. I have had an excellent experience during each of my visits, and I highly recommend this hotel to others"
qader 2-night trip
Posted 4 days ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
10,348
Accommodation
2 Condo Rentals
Lowest Price
$87
Highest Price
$327

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