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Gainesboro Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Gainesboro vacation rentals

A hot tub on a wooden deck with an American flag, string lights, and a view of the landscape.

1. Large Glamper w/ Hot Tub and full bathroom-sleep 6

Large Glamper w/ Hot Tub and full bathroom-sleep 6
Capon Bridge
9.8 out of 10, Exceptional, (25 reviews)
"I can't express enough how appreciative we are to the owner and manager. Best time I've had in years. "
United States
Mary
$214 nightly
The price is $239
Sep 28 - Sep 29
Total with taxes and fees
Large Glamper w/ Hot Tub and full bathroom-sleep 6
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

2. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Winchester Historic District
10.0 out of 10, Exceptional, (2 reviews)
"The unit is very nice, exactly as described, The bed are comfortable and everything was fine. The location is excellent very near to historical sights and downtown shopping district."
United States
Timothy B.
$229 nightly
The price is $259
Sep 27 - Sep 28
Total with taxes and fees
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A living room with a sofa, armchair, coffee table, and a television.

3. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.2 out of 10, Wonderful, (18 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
$294 nightly
The price is $333
Sep 27 - Sep 28
Total with taxes and fees
Nostalgia Lane in the heart of the city
A living room with a sofa, a coffee table, a fireplace, a television, and a dining area in the background.

4. Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.6 out of 10, Exceptional, (8 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
$346 nightly
The price is $392
Sep 27 - Sep 28
Total with taxes and fees
Scarborough Fair walk to downtown two story apt
A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

5. 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, (12 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
$223 nightly
The price is $253
Sep 27 - Sep 28
Total with taxes and fees
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
A dining area with a white table and bench, a hanging light fixture, and a door leading to another room.

6. 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.
$327 nightly
The price is $370
Oct 4 - Oct 5
Total with taxes and fees
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
A two-story house with a front porch, a mailbox, and a number plate.

7. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.6 out of 10, Exceptional, (9 reviews)
"The property was exceptional and very comfortable. We enjoyed the amenities. We would book it for future trips again."
United States
Carolyn F.
$308 nightly
The price is $349
Sep 27 - Sep 28
Total with taxes and fees
Cameron Charmer pristine downtown apt with double master suites
A living room with a sofa, ottoman, lamp, and a mirror.

8. 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.
$273 nightly
The price is $309
Oct 1 - Oct 2
Total with taxes and fees
Morocco Loft 2BR overlooking city walking mall

9. 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
$343 nightly
The price is $364
Sep 28 - Sep 29
Total with taxes and fees
Enchanted Mountain Cabin Retreat with Woodland Serenity near Sleepy Creek Lake West Virginia
A hot tub on a wooden deck with a red umbrella, surrounded by greenery and a clear sky.

10. Modern w Mountain Views, Hot Tub, Deck & Fire Pit

Modern w Mountain Views, Hot Tub, Deck & Fire Pit
Berkeley Springs
9.4 out of 10, Exceptional, (14 reviews)
"Amazing cabin getaway "
United States
Aleks S.
$261 nightly
The price is $280
Sep 27 - Sep 28
Total with taxes and fees
Modern w Mountain Views, Hot Tub, Deck & Fire Pit

11. Forest Haven Chalet Cabin

Forest Haven Chalet Cabin
Gerrardstown
$256 nightly
The price is $285
Sep 27 - Sep 28
Total with taxes and fees
Forest Haven Chalet Cabin

12. 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.
$295 nightly
The price is $318
Sep 30 - Oct 1
Total with taxes and fees
Stone chalet w/ views & hot tub
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

13. 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.
$203 nightly
The price is $230
Sep 27 - Sep 28
Total with taxes and fees
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A compact kitchen with a central island, wooden cabinets, a microwave, and a refrigerator.

14. Buena Vista

Buena Vista
Shawneeland
10.0 out of 10, Exceptional, (1 review)
$217 nightly
The price is $220
Sep 29 - Sep 30
Total with taxes and fees
Buena Vista
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

15. 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.
$170 nightly
The price is $193
Sep 27 - Sep 28
Total with taxes and fees
Rosamond nice downtown studio apt

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

Fantastic Cabin with Barbecue and Hot-tub in Gerrardstown, West Virginia
Gerrardstown
$330 nightly
The price is $349
Sep 28 - Sep 29
Total with taxes and fees
Fantastic Cabin with Barbecue and Hot-tub in Gerrardstown, West Virginia
A high-ceilinged room with large windows, a wooden interior, a sofa, a coffee table, and a fireplace.

17. Upscale w Fireplace, Fire Pit, Games in Gated Comm

Upscale w Fireplace, Fire Pit, Games in Gated Comm
Paw Paw
9.8 out of 10, Exceptional, (9 reviews)
"Loved our stay overall. Beautiful decor, cozy and remote location. Great communication with host as well. Perfect spot to get away from the hustle and stresses of daily work life. "
United States
Jella S.
$336 nightly
The price is $365
Sep 27 - Sep 28
Total with taxes and fees
Upscale w Fireplace, Fire Pit, Games in Gated Comm
A two-story house with a balcony, surrounded by trees and a wooded area.

18. Lofted Quaint Cabin with BBQ and Mountain Views in West Virginia

Lofted Quaint Cabin with BBQ and Mountain Views in West Virginia
Gerrardstown
$243 nightly
The price is $270
Sep 27 - Sep 28
Total with taxes and fees
Lofted Quaint Cabin with BBQ and Mountain Views in West Virginia

19. 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
$285 nightly
The price is $302
Oct 1 - Oct 2
Total with taxes and fees
Stone Cabin with Amazing Views, Hot Tub, Fire Pit and Game Room Perfect for Your Gerrardstown, WV Getaway

20. Forest cabin w/ hot tub, deck & huge yard

Forest cabin w/ hot tub, deck & huge yard
Gerrardstown
8.0 out of 10, Very good, (3 reviews)
"The house has real potential, but also has real problems. It needs some maintenance in a major way. The toilet won’t flush. The faucet in the bathtub fell off. The grill had not been cleaned in so long that it broke out into a fire. When communicated these problems with the host, the response was I’m sorry for the inconvenience. We will have our handyman fix it after you leave. Frankly, I wanted it fixed while we were there. They also did not provide the necessary materials for cleaning dishes....
United States
Heather H.
$274 nightly
The price is $295
Sep 28 - Sep 29
Total with taxes and fees
Forest cabin w/ hot tub, deck & huge yard
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

Microtel Inn & Suites by Wyndham Winchester

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."
Masdester 2-night trip
Posted 1 hour ago
Microtel Inn & Suites by Wyndham Winchester

Find out more about Gainesboro

Everything you need to know about Gainesboro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gainesboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gainesboro vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gainesboro vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gainesboro. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Gainesboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $181 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Gainesboro rentals

At Expedia, we put the best Gainesboro vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Gainesboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gainesboro vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gainesboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Gainesboro?

Yes, we have vacation rentals near well known points of interest in Gainesboro, or you can go with a secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Gainesboro has to offer?

A-Frame Mountain Retreat: Visitors like this Gainesboro vacation home rental. It offers a patio, a selection of games, and a barbecue grill 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 vacation with amenities like a 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 larger area, you’ll find Peacemaker National Training Center and Rock Harbor Golf Course.

What’s a vacation rental in Gainesboro like?

A vacation rental is a private property where you can stay for short or long periods in Gainesboro. Vacation rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family trips.