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Our top choices for Gainesboro hotels

1. Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,449 reviews)
"Perfect accommodation- great breakfast and attentive gracious staff"
United States
Kathleen
The price is CA $115
CA $128 total
includes taxes & fees
Nov 12 - Nov 13
Microtel Inn & Suites by Wyndham Winchester

2. TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,005 reviews)
"Rooms good sized, beds comfortable, quiet ( slept great), great breakfast. Highly recommend!!"
United States
Jesse
The price is CA $115
CA $128 total
includes taxes & fees
Nov 22 - Nov 23
TRU By Hilton Winchester

3. Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,007 reviews)
"The room was clean and the staff was very nice and helpful. Breakfast was good as well."
United States
james
The price is CA $102
CA $114 total
includes taxes & fees
Nov 16 - Nov 17
Quality Inn Winchester

4. Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
2.5 star property
Winchester
9.0 out of 10, Wonderful, (871 reviews)
"Very clean comfortable bed good breakfast"
United States
David
The price is CA $161
CA $179 total
includes taxes & fees
Dec 10 - Dec 11
Holiday Inn Express Hotel & Suites Winchester by IHG

5. Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (1,010 reviews)
"Clean room, great staff, good parking and free breakfast"
United States
Albert
The price is CA $92
CA $104 total
includes taxes & fees
Dec 6 - Dec 7
Spark by Hilton Winchester

6. SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (915 reviews)
"Great place to stay"
United States
Roy
The price is CA $160
CA $178 total
includes taxes & fees
Nov 23 - Nov 24
SpringHill Suites by Marriott Winchester

7. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (972 reviews)
"Great place to stay in Winchester."
United States
Thomas
The price is CA $131
CA $146 total
includes taxes & fees
Nov 16 - Nov 17
Fairfield Inn & Suites by Marriott Winchester

8. Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,003 reviews)
"We had an amazing stay and will be back! The rooms were clean and comfy and staff were very helpful."
United States
Jessica
The price is CA $151
CA $168 total
includes taxes & fees
Nov 23 - Nov 24
Courtyard by Marriott Winchester

9. Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester
2.0 star property
Winchester
6.6 out of 10, (607 reviews)
"Rooms were dated but very clean. Room was quiet and beds were comfortable. Plentiful hot water for showers."
United States
karen
The price is CA $89
CA $99 total
includes taxes & fees
Nov 15 - Nov 16
Days Inn by Wyndham Winchester

10. La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (2,275 reviews)
"Great place to stay the night after a long drive"
United States
lucy
The price is CA $146
CA $163 total
includes taxes & fees
Nov 15 - Nov 16
La Quinta Inn & Suites by Wyndham Winchester

11. Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
Winchester
9.2 out of 10, Wonderful, (964 reviews)
"The breakfast was delicious, it was very welcoming very clean best ever had at motel"
United States
Elizabeth
The price is CA $149
CA $169 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn Winchester N/Conference Center, VA

12. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,156 reviews)
"Convenient to the highway and reasonably priced."
United States
Donna S.
The price is CA $123
CA $137 total
includes taxes & fees
Nov 30 - Dec 1
Comfort Inn & Suites Winchester

13. Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1,006 reviews)
"Comfortable bed, friendly staff, and convenient location"
United States
Zohair
The price is CA $119
CA $132 total
includes taxes & fees
Nov 30 - Dec 1
Country Inn & Suites by Radisson, Winchester, VA

14. Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1,076 reviews)
"Clean room, good staff, good location"
United States
Gregory
The price is CA $99
CA $109 total
includes taxes & fees
Dec 10 - Dec 11
Travelodge by Wyndham Winchester

15. Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG
2.5 star property
Winchester
8.8 out of 10, Excellent, (657 reviews)
"Nice place to stay. Convenient for our travels."
United States
marilyn
The price is CA $113
CA $126 total
includes taxes & fees
Nov 15 - Nov 16
Candlewood Suites Winchester by IHG

16. Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.6 out of 10, Good, (1,006 reviews)
"I had a good stay and staff was friendly"
United States
Leah
The price is CA $90
CA $100 total
includes taxes & fees
Dec 6 - Dec 7
Sleep Inn & Suites Winchester near University

17. Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,007 reviews)
"Great hotel."
United States
Nicholas
The price is CA $140
CA $160 total
includes taxes & fees
Dec 8 - Dec 9
Holiday Inn Winchester Se-Historic Gateway by IHG

18. Home2 Suites By Hilton Winchester

Home2 Suites By Hilton Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (51 reviews)
"Clean rooms , friendly staff."
United States
Jean
The price is CA $125
CA $142 total
includes taxes & fees
Nov 22 - Nov 23
Home2 Suites By Hilton Winchester

19. Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
Stephens City
8.2 out of 10, Very good, (926 reviews)
"Great hotel"
United States
Michael
The price is CA $113
CA $126 total
includes taxes & fees
Dec 8 - Dec 9
Holiday Inn Express Winchester South-Stephens City by IHG

20. TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (534 reviews)
"Always a great place to land!! Love the location!! Great walking areas, a grocery store and lots of restaurants within walking distance!! Many many good wineries as well!!"
United States
Lori
The price is CA $160
CA $178 total
includes taxes & fees
Nov 15 - Nov 16
TownePlace Suites by Marriott Winchester
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 Gainesboro Hotel Reviews

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Hotels in Gainesboro with star rating

Frequently asked questions

What is the best area to stay in Gainesboro?
For most visitors, the best area to stay in Gainesboro is the historic downtown district, particularly around Main Street.

This central area offers a blend of historic charm and modern conveniences. Main Street is the heart of Gainesboro, lined with independent shops, local eateries, and a few boutique hotels. You'll find the Gainesboro Town Hall and the historic Gainesboro Theatre within easy walking distance. The streets are generally well-maintained and easy to navigate on foot.

Couples looking for a relaxing getaway will appreciate the downtown area. It provides a pleasant setting for strolls, dining at local restaurants, and exploring the small art galleries. The proximity to local parks, such as Gainesboro City Park, allows for quiet afternoons outdoors.

Families will also find downtown Gainesboro convenient. Many accommodations here offer family-friendly amenities, and the central location means easy access to local attractions like the Gainesboro Children's Museum and the community swimming pool.
When is the best time to go to Gainesboro?
The best time to visit Gainesboro is during the spring (April to May) and autumn (September to October) months when the weather is mild and the natural beauty of the Shenandoah Valley is at its peak.

Spring brings pleasant temperatures, typically ranging from 15°C to 25°C, making it ideal for outdoor activities like hiking and exploring the local vineyards. The blooming wildflowers and fruit orchards create picturesque scenery, great for those who enjoy photography or leisurely strolls. This period is particularly good for couples looking for a romantic getaway with scenic drives and wine-tasting experiences.

Autumn offers equally comfortable weather, with temperatures usually between 10°C and 20°C, and the added spectacle of vibrant fall foliage. The changing colours of the leaves across the Blue Ridge Mountains are truly breathtaking and draw many visitors to the area. This season is excellent for solo travellers or couples interested in scenic drives along the Skyline Drive or exploring the numerous apple orchards and harvest festivals.

While summer (June to August) is also popular, temperatures can be warmer and more humid, occasionally reaching above 30°C. Winter (November to March) can be quite cold, with occasional snow, which might limit some outdoor activities.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Gainesboro.
How much is the nightly rate at a Gainesboro hotel?
Prices for hotels in Gainesboro often vary, but you can find a great deal from CA $99 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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