Gainesboro Holiday Rentals, Winchester: Private House Rentals

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Our top choices for Gainesboro hotels

A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.

An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.

A modern hotel with a flat facade, multiple windows, and a well-lit entrance.

A gym with treadmills, elliptical machines, and dumbbells.

1. La Quinta Inn & Suites by Wyndham Winchester

Winchester

Earl

฿3,779

฿4,206 total

includes taxes & fees

28 Sept - 29 Sept

A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.

A modern lounge area with seating, a TV, and a children's play area.

A hotel reception area with a wooden reception desk, two computers, a map of the USA on the wall, and a small plant on the desk.

A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

2. Microtel Inn & Suites by Wyndham Winchester

Winchester

Marcia

฿3,401

฿3,785 total

includes taxes & fees

25 Oct - 26 Oct

A self-service beverage station with a refrigerated drink dispenser, a coffee machine, and a variety of snacks.

An indoor swimming pool with clear lane markings, a lifeguard chair, and a safety ring on the wall.

A modern lounge area with seating arrangements, including sofas and chairs, and a large window providing a view outside.

A spacious restaurant with a central island, seating areas, and a mural on the back wall.

3. TRU By Hilton Winchester

Winchester

Kailyn

฿3,266

฿3,635 total

includes taxes & fees

4 Oct - 5 Oct

A hotel dining area with multiple tables and chairs, large windows, and a television screen.

A hotel room with a television, desk, chair, sofa, and kitchenette.

4. Comfort Inn & Suites Winchester

Winchester

John

฿3,129

฿3,482 total

includes taxes & fees

18 Oct - 19 Oct

An outdoor patio with a fire feature, seating, and a covered area.

A modern hotel with a covered entrance, a sign reading "SPRINGHILL SUITES BY MARRIOTT," and a landscaped area with plants.

A modern hotel lobby with a large dining area, wooden accents, and contemporary lighting fixtures.

An indoor swimming pool with clear water, metal railings, and lounge chairs.

5. SpringHill Suites by Marriott Winchester

Winchester

Michael

฿4,094

฿4,557 total

includes taxes & fees

4 Oct - 5 Oct

A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.

A Holiday Inn Express & Suites building with a covered entrance, large windows, and a fire lane.

An indoor swimming pool with a lifeguard chair, a pool lift, and a window.

A hotel room with a bed, a desk, a chair, a window with a view, and a TV on the wall.

6. Holiday Inn Express Hotel & Suites Winchester by IHG

Winchester

Gregory.

฿3,950

฿4,396 total

includes taxes & fees

25 Oct - 26 Oct

A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.

A modern kitchen with wooden cabinets, a countertop, and a window with a view.

A hotel room with a large bed, a bedside table with a lamp, a small desk, and a kitchenette area.

A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.

7. Hampton Inn Winchester N/Conference Center, VA

Winchester

Michael

฿3,211

฿3,638 total

includes taxes & fees

19 Oct - 20 Oct

A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.

A hotel room with two beds, a desk, a chair, a desk lamp, and a large window with curtains.

A modern hotel lobby with a curved sofa, a glass coffee table, and a flat-screen TV mounted on the wall.

An outdoor seating area with wicker furniture and a small table, surrounded by greenery and a building in the background.

8. Courtyard by Marriott Winchester

Winchester

Karen

฿3,580

฿3,984 total

includes taxes & fees

4 Oct - 5 Oct

A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.

A swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.

A hotel reception area with a black counter, coffee dispensers, a juice dispenser, and a small refrigerator.

A hotel lobby with a blue sofa, red chairs, a patterned rug, and artwork on the walls.

9. Quality Inn Winchester

Winchester

Joseph

฿2,817

฿3,135 total

includes taxes & fees

25 Oct - 26 Oct

A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.

A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

A coffee station with multiple coffee dispensers and a sign above.

A modern restaurant interior with wooden tables and chairs, a green booth area, and artwork on the walls.

10. Fairfield Inn & Suites by Marriott Winchester

Winchester

Dawn

฿3,097

฿3,447 total

includes taxes & fees

28 Sept - 29 Sept

A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".

An indoor swimming pool with clear glass walls, a tiled floor, and a few lounge chairs.

A modern indoor space with a long wooden table and benches, surrounded by chairs and a green carpet.

A hotel with a modern design, featuring a prominent 'spark by Hilton' sign, a well-lit entrance, and a landscaped front yard.

11. Spark by Hilton Winchester

Winchester

Peter

฿2,618

฿2,967 total

includes taxes & fees

4 Oct - 5 Oct

A courtyard with a fountain, tables with white tablecloths, and brick buildings.

A spacious lobby with a round table, chairs, a chandelier, and an American flag.

A large brick building with a classic facade, a central entrance with a decorative arch, and a sign reading "The George Washington Hotel."

A spacious living room with a fireplace, leather sofa, armchairs, and a large painting.

12. The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

Carol

฿4,364

฿4,944 total

includes taxes & fees

4 Oct - 5 Oct

A hotel lobby with seating, a reception desk, and a refrigerated display.

A compact kitchen with a microwave, stove, dishwasher, and sink. There is a dining area with a table and chairs, and a living room with a sofa.

A modern lobby with two armchairs, a coffee station, and a snack bar.

An outdoor patio with round tables and chairs, red umbrellas, and a brick building in the background.

13. TownePlace Suites by Marriott Winchester

Winchester

Katherine

฿3,779

฿4,206 total

includes taxes & fees

30 Sept - 1 Oct

A hotel room with two beds, a blue armchair, a nightstand with a lamp, and a wall-mounted painting.

A hotel with a registration sign, a parking lot, and a tree in front.

A seating area with two chairs and a lamp, a sign indicating continental breakfast hours, and a door with a small window.

A seating area with two blue leather chairs and a beverage vending machine.

14. Days Inn by Wyndham Winchester

Winchester

Lawrence

฿2,106

฿2,344 total

includes taxes & fees

28 Sept - 29 Sept

A spacious living room with a fireplace, wooden staircase, and a bookshelf.

A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

A poolside area with lounge chairs and a stack of towels on a table.

A woman using a stationary bike in a gym with red walls and multiple exercise machines.

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

Winchester

Allen

฿3,150

฿3,506 total

includes taxes & fees

25 Oct - 26 Oct

A modern living room with a sofa, armchair, dining table, and chairs. There is a TV mounted on the wall and a small table with a lamp.

A hotel room with a sofa, a desk, a TV, a dresser, and a bed.

A spacious indoor area with a long table and chairs, a statue, and a large window.

A hotel room with two beds, a wooden headboard, a nightstand with lamps, and a view of the outdoors through the window.

16. Travelodge by Wyndham Winchester

Winchester

john

฿2,306

฿2,544 total

includes taxes & fees

28 Sept - 29 Sept

A gym with treadmills, exercise balls, and a mirrored wall.

A hotel room with a wooden floor, a round table, and two chairs. There is a lamp on a side table and a large window with curtains.

A Hampton Inn hotel with a modern facade, a covered entrance, and a landscaped front yard.

A modern living room with a sofa, chairs, a coffee table, and a TV mounted on the wall.

17. Hampton Inn Winchester-University/Mall Area

Winchester

Henedina

฿3,634

฿4,117 total

includes taxes & fees

25 Oct - 26 Oct

A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

A swimming pool with lounge chairs and a changing room.

A hotel room with a bed, a desk with a computer, a chair, and a TV.

A spacious lobby with a checkered floor, a reception desk, and a seating area with a sofa and chairs.

18. Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

Jennifer

฿3,448

฿3,937 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a bed, a brown sofa, a round table, a lamp, a window with a decorative screen, and a framed picture on the wall.

A reception area with a wooden desk, a black rug, and a patterned wall.

A modern hotel room with a large desk, a comfortable sofa, a flat-screen TV, and a large window with a view.

A modern kitchen with dark cabinets, a white countertop, a built-in microwave, and a coffee maker.

19. Candlewood Suites Winchester by IHG

Winchester

Bridget

฿3,247

฿3,614 total

includes taxes & fees

28 Sept - 29 Sept

An outdoor patio with a grill, seating, and string lights.

A modern breakfast bar with a variety of food items, a coffee machine, and a fruit display.

20. Home2 Suites By Hilton Winchester

Winchester

Mandy

฿3,156

฿3,576 total

includes taxes & fees

26 Oct - 27 Oct

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Top Gainesboro Hotel Reviews

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent

"Although we didn’t get a handicap-accessible room, the staff was incredibly accommodating and went above and beyond to ensure my mother’s comfort. The housekeeping was exceptional, and the front desk staff was incredibly understanding and patient. Overall, we had a fantastic trip."

Days Inn by Wyndham Winchester

10/10 Excellent

"Great place"

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent

"great ,good price"

TRU By Hilton Winchester

10/10 Excellent

"Great Location & Customer Service"

Travelodge by Wyndham Winchester

8/10 Good

"The shampoo/conditioner actually worked without additional conditioner. I was able to come through my hair with little issue."

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"Excellent in all aspects of the stay. My go to when visiting my son. 3rd time here and never disappointed. Staff so nice property kept up well. Beds so comfortable you don’t want to get up. Coffee always available in the lobby. Also wine available for sale. Love love it ."

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent

"Fabulous mini-frills hotel. Staff is exemplary and efficient, courteous and kind. Rooms are spacious and clean. Great stop on your way here, there, and everywhere!"

Holiday Inn Express Winchester South-Stephens City by IHG

8/10 Good

"The hotel and all amenities were fine. When I went to check in I was told I had gone through a search site to book the room, which I had not. I booked directly with them, I had to get that clear before I could use my AAA discount."

More cheap stays in Gainesboro

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA

฿2,306

฿2,544 total

28 Sept - 29 Sept

includes taxes & fees

8.6/10 Excellent! (1,076 reviews)

Quality Inn Winchester

1601 Martinsburg Pike Winchester VA

฿2,817

฿3,135 total

25 Oct - 26 Oct

includes taxes & fees

Comfort Inn & Suites Winchester

195 Kernstown Commons Blvd Winchester VA

฿3,129

฿3,482 total

18 Oct - 19 Oct

includes taxes & fees

9.4/10 Exceptional! (1,135 reviews)

TRU By Hilton Winchester

118 Mercedes Court Winchester VA

฿3,266

฿3,635 total

4 Oct - 5 Oct

includes taxes & fees

9.2/10 Wonderful! (1,002 reviews)

Hampton Inn Martinsburg

975 Foxcroft Ave Martinsburg WV

฿3,266

฿3,691 total

4 Oct - 5 Oct

includes taxes & fees

8.8/10 Excellent! (1,004 reviews)

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA

฿3,401

฿3,785 total

25 Oct - 26 Oct

includes taxes & fees

9.2/10 Wonderful! (1,454 reviews)

Frequently asked questions

What's the best place for a stay in Gainesboro?

The George Washington Hotel, A Wyndham Grand Hotel, located 8.2 mi (13.2 km) from the heart of Gainesboro, is a top choice for your stay, based on our traveller data. Two other choices for your stay in the area are Travelodge by Wyndham Winchester and TRU By Hilton Winchester. See all available top hotels, or vacation rentals in Gainesboro.

If I need to cancel my hotel reservation in Gainesboro, will I receive a refund?

Yes! The majority of room reservations are fully refundable if you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If your reservation is non-refundable, you might still have the option to cancel and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Gainesboro.

What is staying in Gainesboro like?

Visitors to Gainesboro will definitely find plenty to explore and enjoy. There are 358 hotels and other accommodation options in the surrounding area. Find out more about Gainesboro.

What should I see while I'm in Gainesboro?

Places to visit in the wider area include Peacemaker National Training Center, Rock Harbor Golf Course and Museum of the Shenandoah Valley. You'll also find Bright Box Theater and Shenandoah Valley Discovery Museum in the area. Take a look at what more there is to see and do in Expedia's Gainesboro guide.

What's the seasonal weather like in Gainesboro?

The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Gainesboro is 1172 mm.

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Book Hotels in Gainesboro on Expedia.com

Find hotels in Gainesboro, VA from ฿2,344

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Gainesboro

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Gainesboro hotels

1. La Quinta Inn & Suites by Wyndham Winchester

2. Microtel Inn & Suites by Wyndham Winchester

3. TRU By Hilton Winchester

4. Comfort Inn & Suites Winchester

5. SpringHill Suites by Marriott Winchester

6. Holiday Inn Express Hotel & Suites Winchester by IHG

7. Hampton Inn Winchester N/Conference Center, VA

8. Courtyard by Marriott Winchester

9. Quality Inn Winchester

10. Fairfield Inn & Suites by Marriott Winchester

11. Spark by Hilton Winchester

12. The George Washington Hotel, A Wyndham Grand Hotel

13. TownePlace Suites by Marriott Winchester

14. Days Inn by Wyndham Winchester

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

16. Travelodge by Wyndham Winchester

17. Hampton Inn Winchester-University/Mall Area

18. Holiday Inn Winchester Se-Historic Gateway by IHG

19. Candlewood Suites Winchester by IHG

20. Home2 Suites By Hilton Winchester

Top Gainesboro Hotel Reviews

Microtel Inn & Suites by Wyndham Winchester

Days Inn by Wyndham Winchester

Fairfield Inn & Suites by Marriott Winchester

TRU By Hilton Winchester

Travelodge by Wyndham Winchester

Country Inn & Suites by Radisson, Winchester, VA

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

More cheap stays in Gainesboro

Travelodge by Wyndham Winchester

Quality Inn Winchester

Comfort Inn & Suites Winchester

TRU By Hilton Winchester

Hampton Inn Martinsburg

Microtel Inn & Suites by Wyndham Winchester

Frequently asked questions

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