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Gainesboro Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Gainesboro holiday rentals

A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

1. Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Old Town Winchester
10.0 out of 10, Exceptional, (15 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is HK$1,530
HK$2,747 total
includes taxes & fees
25 Oct - 26 Oct
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
A living room with a sofa, ottoman, lamp, and a mirror.

2. Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is HK$1,395
HK$2,557 total
includes taxes & fees
27 Oct - 28 Oct
Morocco Loft 2BR overlooking city walking mall
Forest Haven is beautiful at night

3. Forest 2BR chalet w/ hot tub & backyard

Forest 2BR chalet w/ hot tub & backyard
Gerrardstown
9.6 out of 10, Exceptional, (5 reviews)
"Just an overnight stay. On our way back home from northern New York. The place was nice. It is peaceful sitting on the deck. The check in process was a little tedious with various emails and downloads required. The Backstep is a little sketchy. Be careful walking in. Overall the place was nice"
United States
John Z.
The price is HK$1,260
HK$2,663 total
includes taxes & fees
25 Oct - 26 Oct
Forest 2BR chalet w/ hot tub & backyard
A two-story house with a front porch, a mailbox, and a number plate.

4. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.8 out of 10, Exceptional, (11 reviews)
"The property was exceptional and very comfortable. We enjoyed the amenities. We would book it for future trips again."
United States
Carolyn F.
The price is HK$1,552
HK$2,735 total
includes taxes & fees
25 Oct - 26 Oct
Cameron Charmer pristine downtown apt with double master suites
Grab a towel and relax in the hot tub

5. Stone chalet w/ views & hot tub

Stone chalet w/ views & hot tub
Gerrardstown
9.0 out of 10, Wonderful, (44 reviews)
"Lovely, cozy cabin. Hot tub was very relaxing. Overall a wonderful place to stay."
United States
Michael H.
The price is HK$1,469
HK$2,938 total
includes taxes & fees
9 Nov - 10 Nov
Stone chalet w/ views & hot tub
Private kitchen

6. Enchanted Mountain Cabin Retreat with Woodland Serenity near Sleepy Creek Lake West Virginia

Enchanted Mountain Cabin Retreat with Woodland Serenity near Sleepy Creek Lake West Virginia
Gerrardstown
The price is HK$2,975
HK$3,781 total
includes taxes & fees
2 Nov - 3 Nov
Enchanted Mountain Cabin Retreat with Woodland Serenity near Sleepy Creek Lake West Virginia
A living room with a TV, two sofas, a coffee table, and a large plant.

7. Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly

Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
Gerrardstown
9.0 out of 10, Wonderful, (12 reviews)
"We had a fabulous time and highly recommend this rental."
United States
Amber H.
The price is HK$1,514
HK$2,891 total
includes taxes & fees
18 Nov - 19 Nov
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

8. Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Old Town Winchester
The price is HK$1,326
HK$2,550 total
includes taxes & fees
3 Nov - 4 Nov
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Interior

9. Fantastic Cabin with Barbecue and Hot-tub in Gerrardstown, West Virginia

Fantastic Cabin with Barbecue and Hot-tub in Gerrardstown, West Virginia
Gerrardstown
The price is HK$2,975
HK$3,781 total
includes taxes & fees
29 Oct - 30 Oct
Fantastic Cabin with Barbecue and Hot-tub in Gerrardstown, West Virginia
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

10. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.8 out of 10, Excellent, (3 reviews)
"Easy space for a 2 person weekend getaway, very close within walking distance to food, shops, breweries, etc"
United States
Jameson D.
The price is HK$863
HK$1,520 total
includes taxes & fees
12 Nov - 13 Nov
Rosamond nice downtown studio apt
Property grounds

11. Stone Cabin with Amazing Views, Hot Tub, Fire Pit and Game Room Perfect for Your Gerrardstown, WV Getaway

Stone Cabin with Amazing Views, Hot Tub, Fire Pit and Game Room Perfect for Your Gerrardstown, WV Getaway
Gerrardstown
The price is HK$3,395
HK$4,317 total
includes taxes & fees
9 Nov - 10 Nov
Stone Cabin with Amazing Views, Hot Tub, Fire Pit and Game Room Perfect for Your Gerrardstown, WV Getaway
A spacious living area with a stone wall, a fireplace, a blue sofa, and a kitchen with wooden cabinets and a large window.

12. Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
7.8 out of 10, Good, (24 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
The price is HK$1,066
HK$2,530 total
includes taxes & fees
25 Oct - 26 Oct
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Room

13. Secluded Chalet-Cabin with Hot Tub, Fire Pit, Deck and Grill - the Perfect Place to Relax in Gerrardstown, WV

Secluded Chalet-Cabin with Hot Tub, Fire Pit, Deck and Grill - the Perfect Place to Relax in Gerrardstown, WV
Gerrardstown
The price is HK$3,368
HK$4,179 total
includes taxes & fees
16 Nov - 17 Nov
Secluded Chalet-Cabin with Hot Tub, Fire Pit, Deck and Grill - the Perfect Place to Relax in Gerrardstown, WV
A living room with a sofa, armchair, coffee table, and a television.

14. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
8.8 out of 10, Excellent, (21 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
The price is HK$1,450
HK$2,610 total
includes taxes & fees
25 Oct - 26 Oct
Nostalgia Lane in the heart of the city
A wooden deck with wicker furniture, including two chairs and a small table with a candle.

15. Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
8.8 out of 10, Excellent, (10 reviews)
"Great location and extremely easy in and out. Cute and clever little apartment. Quirky kitchen set up, but absolutely everything was provided, and I cooked 9 out of 10 nights."
United States
Wayne C.
Cozy English Basement Apt quiet but close to downtown
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

16. Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester Historic District
8.4 out of 10, Very good, (6 reviews)
"Loved being so close to the old town; was able to walk to a lot of places. Great to have an assigned parking spot in a lot behind the building. Enjoyed staying here a lot!"
United States
Leslie L.
The price is HK$1,081
HK$1,838 total
includes taxes & fees
22 Nov - 23 Nov
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Outdoor spa tub

17. Forest Haven Chalet Cabin

Forest Haven Chalet Cabin
Gerrardstown
The price is HK$3,020
HK$3,747 total
includes taxes & fees
25 Oct - 26 Oct
Forest Haven Chalet Cabin
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

18. The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.6 out of 10, Good, (8 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
The price is HK$589
HK$1,953 total
includes taxes & fees
26 Oct - 27 Oct
The Queen of Winchester Three Bedroom with Upper Level Deck
A dining area with a white table and bench, a hanging light fixture, and a door leading to another room.

19. WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Old Town Winchester
9.0 out of 10, Wonderful, (10 reviews)
"Great location…"
United States
John P.
The price is HK$1,607
HK$2,930 total
includes taxes & fees
26 Oct - 27 Oct
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
A hot tub in front of a wooden cabin with a tree in the background.

20. Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (14 reviews)
"The house was wonderfully situated and stocked for our needs. It is very well kept and decorated. We enjoyed our stay very much!"
United States
Shawn P.
The price is HK$1,136
HK$1,439 total
includes taxes & fees
22 Nov - 23 Nov
Luxury tiny home farm stay on historic property with hot tub in Stephens City
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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"Very friendly and helpful staff! Will definitely stay again."
Bonnie 1-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Winchester, VA

Find out more about Gainesboro

Search for holiday rentals in Gainesboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Gainesboro using one of the methods below:

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Look no further and take a look at our great range of rental properties in Gainesboro!

Frequently asked questions

Can I find a holiday rental in Gainesboro?

Yes, there are holiday rentals close to the most popular sights in Gainesboro, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Gainesboro has to offer?

A-Frame Mountain Retreat: This holiday home rental outside of Gainesboro offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

What’s there to see and do in Gainesboro?

Explore the area and family-friendly sights such as Shenandoah Valley Discovery Museum, or get out into nature at a spot like Cacapon Resort State Park. In the wider area, you’ll find Peacemaker National Training Center and Rock Harbor Golf Course.

What’s a holiday rental in Gainesboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Gainesboro. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for families.