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

Lodges in Winchester

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25
In one month
Nov 6 - Nov 8
In two months
Dec 4 - Dec 6
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

A lakeside park with picnic tables and a concrete walkway.

1. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
$75 nightly
The price is $81
Oct 8 - Oct 9
Total with taxes and fees
2 private mountain RV pads for rent. Full hook ups
A two-story house with a red door, green shutters, and a snow-covered front yard.

2. Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (182 reviews)
"Excellent host making us feel very welcome. Very nice room and really lovely breakfast. Would certainly stay again if we are in the area."
United Kingdom
Alan
$168 nightly
The price is $177
Oct 21 - Oct 22
Total with taxes and fees
Centennial House
A bedroom with a geometric-patterned headboard, a bed with a textured white duvet, two pillows, a bedside table with a clock, and a potted plant.

3. Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
9.4 out of 10, Exceptional, (66 reviews)
"Clean rooms, comfortable beds, smooth remote check-in with door code, showerhead was great and the barn door into the bathroom was a unique use of space. We enjoyed our stay."
United States
Donna
$128 nightly
The price is $143
Oct 11 - Oct 12
Total with taxes and fees
Windmill Motel Restaurant
A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.

4. The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (407 reviews)
"The staff was very friendly. Nice, quiet stay. The hotel is outdated but it was very clean, I would stay again."
United States
Heather
$125 nightly
The price is $140
Nov 1 - Nov 2
Total with taxes and fees
The Inn At Crumpin Fox
A hotel room with two beds, a TV, a desk, and a window with curtains.

5. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,003 reviews)
"convenient and safe place to stay while on a drivng vacation through New England"
United States
CHERYL
$92 nightly
The price is $100
Oct 27 - Oct 28
Total with taxes and fees
Days Inn by Wyndham Keene NH
A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.

6. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,000 reviews)
"Bed was more comfortable than most, shower was great and breakfast was good"
United States
Angelo
$119 nightly
The price is $129
Nov 2 - Nov 3
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel
A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.

7. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (880 reviews)
"Very nice staff and enjoyed my stay."
United States
Charlene
$113 nightly
The price is $125
Nov 1 - Nov 2
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91
A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.

8. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
9.0 out of 10, Wonderful, (1,003 reviews)
"Staff was great. The amenities were great. Very clean. Breakfast was very good. I would certainly recommend it and return myself."
Canada
Paul
$152 nightly
The price is $167
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express Hotel & Suites Brattleboro by IHG
A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.

9. Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (1,000 reviews)
"Great place for overnight stay"
United States
Francesca
$117 nightly
The price is $129
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn Brattleboro
The exterior of Latchis Hotel with a prominent entrance, large windows, and potted plants.

10. Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (999 reviews)
"Great time in Brattleboro"
United States
jeffrey
$142 nightly
The price is $157
Nov 2 - Nov 3
Total with taxes and fees
Latchis Hotel
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.

11. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,000 reviews)
"Great place to go"
United States
Ruddy
$142 nightly
The price is $154
Nov 1 - Nov 2
Total with taxes and fees
Best Western Plus Keene Hotel
A wooden table set with plates, cutlery, and a folded napkin.

12. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (177 reviews)
"Clean,quiet, beautiful inn in the heart of downtown Keene,NH. Joe was friendly and accommodating and a hell of a great guy. A+++++++"
United States
Richard
$158 nightly
The price is $172
Oct 29 - Oct 30
Total with taxes and fees
The Carriage Barn Inn
A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

13. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (418 reviews)
"Nice stay with great workout facilities!"
United States
Rebecca
$140 nightly
The price is $152
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn & Suites Keene
A dock extending into a lake with a grassy area in the foreground and trees in the background.

14. Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (692 reviews)
"Spacious rooms, big balconies overlooking the river, and the whole hotel was VERY clean."
United States
Jason
$152 nightly
The price is $165
Nov 5 - Nov 6
Total with taxes and fees
Riverside Hotel, an Ascend Collection Hotel
A wooden cabin with a thatched roof, accessible via a wooden walkway with railings.

15. Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (246 reviews)
"Great place to stay."
United States
Cecil
$223 nightly
The price is $243
Oct 12 - Oct 13
Total with taxes and fees
Vikings Villages Resort
A historic brick building with a porch and a sign reading "Burrell House."

16. The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (184 reviews)
"Wonderful stay"
United States
Justin
$141 nightly
The price is $153
Oct 21 - Oct 22
Total with taxes and fees
The Burrell House
A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.

17. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.2 out of 10, (684 reviews)
"I was given a key to an occupied room first, then moved to a room that a smoker used, and lastly a musty room that I used. It did have A/C and windows to the parking lot. There is a swimming pool in the center available for tenants."
United States
David
$99 nightly
The price is $109
Nov 5 - Nov 6
Total with taxes and fees
Econo Lodge Brattleboro South
A reception area with a counter, a computer, and various informational posters on the wall.

18. Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (815 reviews)
"Room was in excellent condition , very Clean The vanity and sink on Room was very helpful Parking was a easy View to the mountain was beautiful"
United States
Nicolas
$63 nightly
The price is $69
Oct 8 - Oct 9
Total with taxes and fees
Travelodge by Wyndham Brattleboro VT
A rustic cabin with a covered porch, a small shed, and outdoor seating.

19. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (19 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
$155 nightly
The price is $168
Oct 29 - Oct 30
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A cozy living room with a fireplace, a coffee station, and a view of the outside.

20. Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
6.4 out of 10, (80 reviews)
"I love these kinds of motor lodges and I want them to keep improving and to succeed."
Canada
David
$84 nightly
The price is $93
Nov 1 - Nov 2
Total with taxes and fees
Colonial Motel
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 Putney Inn

The Putney Inn

8/10 Good
"Nice area; motel needs some TLC. Spent three nights while on a sightseeing trip. Overall enjoyed our stay."
Carolyn 3-night trip
Posted 16 hours ago
The Putney Inn

Find out more about Winchester

Winchester Lodges information

Number of reviews
5,463
Accommodation
1 Lodges
Lowest Price
$69
Highest Price
$243

Frequently asked questions

Why book your lodge in Winchester with Expedia?
Booking a lodge in Winchester is as easy as clicking on your travel dates and picking a place that satisfies your needs. Use Expedia's handy filters to tailor your search results and find a dream stay. Whether you're traveling on a shoestring or have big bucks to spend, you're sure to score terrific savings.
How can I find cheap lodges in Winchester?
With Expedia's filter tool, comparing cheap lodges in Winchester couldn't be simpler. To discover properties that'll make your wallet happy, narrow your search by budget, amenities and star rating. Also remember that lodges with lower star ratings are going to be more competitively priced.

Explore a world of travel with Expedia