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Gainesboro Holiday Rentals

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Our top choices for Gainesboro holiday rentals

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, (14 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is NZ$607
includes taxes & fees
20 Oct - 21 Oct
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

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 NZ$528
includes taxes & fees
20 Oct - 21 Oct
Morocco Loft 2BR overlooking city walking mall

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 NZ$598
includes taxes & fees
22 Oct - 23 Oct
Forest 2BR chalet w/ hot tub & backyard

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 NZ$613
includes taxes & fees
20 Oct - 21 Oct
Cameron Charmer pristine downtown apt with double master suites

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 NZ$654
includes taxes & fees
9 Nov - 10 Nov
Stone chalet w/ views & hot tub

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 NZ$852
includes taxes & fees
2 Nov - 3 Nov
Enchanted Mountain Cabin Retreat with Woodland Serenity near Sleepy Creek Lake West Virginia

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 NZ$699
includes taxes & fees
9 Nov - 10 Nov
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly

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 NZ$578
includes taxes & fees
20 Oct - 21 Oct
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

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 NZ$822
includes taxes & fees
22 Oct - 23 Oct
Fantastic Cabin with Barbecue and Hot-tub in Gerrardstown, West Virginia

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 NZ$341
includes taxes & fees
2 Nov - 3 Nov
Rosamond nice downtown studio apt

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 NZ$922
includes taxes & fees
17 Nov - 18 Nov
Stone Cabin with Amazing Views, Hot Tub, Fire Pit and Game Room Perfect for Your Gerrardstown, WV Getaway

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 NZ$569
includes taxes & fees
25 Oct - 26 Oct
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

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 NZ$1,043
includes taxes & fees
9 Nov - 10 Nov
Secluded Chalet-Cabin with Hot Tub, Fire Pit, Deck and Grill - the Perfect Place to Relax in Gerrardstown, WV

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 NZ$585
includes taxes & fees
20 Oct - 21 Oct
Nostalgia Lane in the heart of the city

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.
The price is NZ$311
includes taxes & fees
11 Nov - 12 Nov
Cozy English Basement Apt quiet but close to downtown

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 NZ$407
includes taxes & fees
15 Nov - 16 Nov
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

17. Forest Haven Chalet Cabin

Forest Haven Chalet Cabin
Gerrardstown
The price is NZ$820
includes taxes & fees
22 Oct - 23 Oct
Forest Haven Chalet Cabin

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 NZ$434
includes taxes & fees
16 Nov - 17 Nov
The Queen of Winchester Three Bedroom with Upper Level Deck

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 NZ$653
includes taxes & fees
20 Oct - 21 Oct
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

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 NZ$325
includes taxes & fees
16 Nov - 17 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

Find out more about Gainesboro

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Gainesboro holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Gainesboro. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Gainesboro. Seeing all the best attractions is bound to make you fall in love with Gainesboro. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Gainesboro short-term rentals, that won’t be hard to do.

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.