Upfront pricingOur total price for your stay includes taxes and fees
Treat yourselfSave 10% or more on over 100,000 hotels worldwide with Member Prices
Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Winchester 2-star hotels
1. Best Western Jacksonville Inn
Best Western Jacksonville InnJacksonville
8.4 out of 10, Very good, (871 reviews)
"Staff was very attentive"
Craig
$75 nightly
The price is $85
Dec 13 - Dec 14
Total with taxes and fees
2. Jacksonville Inn & Suites
Jacksonville Inn & SuitesJacksonville
8.2 out of 10, Very good, (75 reviews)
"The staff were very peasant, service great and room amazing. Definitely would stay there again."
Hilda
$89 nightly
The price is $99
Nov 16 - Nov 17
Total with taxes and fees
3. Super 8 by Wyndham Jacksonville
Super 8 by Wyndham JacksonvilleJacksonville
8.2 out of 10, Very good, (674 reviews)
"Nice place for overpnight stay."
Pawel
$58 nightly
The price is $66
Nov 22 - Nov 23
Total with taxes and fees
4. Quality Inn Jacksonville near I-72
Quality Inn Jacksonville near I-72Jacksonville
7.8 out of 10, Good, (525 reviews)
"Good location for our needs."
Michael
$60 nightly
The price is $66
Dec 12 - Dec 13
Total with taxes and fees
5. Holiday Inn Express Hotel & Suites Jacksonville by IHG
Holiday Inn Express Hotel & Suites Jacksonville by IHGJacksonville
7.8 out of 10, Good, (507 reviews)
"Hotel was very clean and well managed. Breakfast buffet was very good and staff helpful. Room was good and bed was very comfortable. Would definetly stay here again as pricing was very reasonable for the king suite."
Thomas
$78 nightly
The price is $87
Nov 22 - Nov 23
Total with taxes and fees
6. Hampton Inn Jacksonville
Hampton Inn JacksonvilleJacksonville
8.8 out of 10, Excellent, (542 reviews)
"The hotel is newly renovated and very clean!! Beds are super comfortable and the breakfast was excellent. They were still working on the fitness room while we were there, so we weren’t able to use that. But overall it was an excellent stay."
Dawn
$84 nightly
The price is $96
Nov 22 - Nov 23
Total with taxes and fees
7. Rodeway Inn Pittsfield
Rodeway Inn PittsfieldPittsfield
6.8 out of 10, (145 reviews)
"We stay everytime we are in town"
Stephanie
$69 nightly
The price is $76
Dec 3 - Dec 4
Total with taxes and fees
8. Monroe Street Suites
Monroe Street SuitesPittsfield
9.8 out of 10, Exceptional, (72 reviews)
"Best place Ive stayed period. 100 percent recommend"
Isidro
$111 nightly
The price is $122
Nov 15 - Nov 16
Total with taxes and fees
9. Green Acres Hotel
Green Acres HotelPittsfield
8.8 out of 10, Excellent, (153 reviews)
"Wonderful place to stay!"
Michele
$137 nightly
The price is $151
Dec 6 - Dec 7
Total with taxes and fees
10. Knights Inn Jacksonville East Morton Ave
Knights Inn Jacksonville East Morton AveJacksonville
6.8 out of 10, (173 reviews)
"Very clean , washer and dryer available ! "
Stacy
$75 nightly
The price is $85
Nov 15 - Nov 16
Total with taxes and fees
11. Idyllic Mt Sterling Retreat w/ Private Lake!
Idyllic Mt Sterling Retreat w/ Private Lake!Mount Sterling
12. West Central Lodging
West Central LodgingPittsfield
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful time - very quiet country location, the manager is friendly but not invasive. First time I have heard a whippoorwill sing in many years. "
Anonymous traveler
Top Winchester Hotel Reviews
Hampton Inn Jacksonville
Hampton Inn JacksonvilleJacksonville
10/10 Excellent
For the price I paid the bed was extremely uncomfortable! The pillows also! Elevator was broke on Sunday when we checked out!
Kathleen