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Gainesboro Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Gainesboro vacation rentals

A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

1. 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
$266 nightly
The price is $302
Nov 10 - Nov 11
Total with taxes and fees
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

2. 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.
$220 nightly
The price is $237
Nov 29 - Nov 30
Total with taxes and fees
The Queen of Winchester Three Bedroom with Upper Level Deck
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

3. 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.
$158 nightly
The price is $179
Nov 12 - Nov 13
Total with taxes and fees
Rosamond nice downtown studio apt
A small wooden cabin with a porch, surrounded by trees.

4. Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV

Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
Berkeley Springs
10.0 out of 10, Exceptional, (3 reviews)
"Everything from booking the stay to arriving and checking in was quick and convenient. The host emailed us directions and was easy to navigate toThe owl was just the perfect size for "
United States
kayla c.
$156 nightly
The price is $164
Nov 10 - Nov 11
Total with taxes and fees
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
A modern living room with a sofa, a coffee table, and a lamp. There is a kitchen area in the background with cabinets and a painting on the wall.

5. Executive Suites

Executive Suites
3.0 star property
Winchester
$252 nightly
The price is $286
Nov 10 - Nov 11
Total with taxes and fees
Executive Suites
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

6. 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
8.8 out of 10, Excellent, (5 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.
$213 nightly
The price is $241
Nov 19 - Nov 20
Total with taxes and fees
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

7. 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.
$190 nightly
The price is $215
Nov 15 - Nov 16
Total with taxes and fees
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A building with a red door, white trim, and a small balcony with a metal railing.

8. The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
7.0 out of 10, Good, (2 reviews)
"Everything went smoothly. Easy stay. Clean. Small efficiency with futon for bed."
United States
Greg A.
$163 nightly
The price is $185
Nov 12 - Nov 13
Total with taxes and fees
The Stock Exchange downtown 3rd floor studio apt
A compact kitchen with a central island, wooden cabinets, a microwave, and a refrigerator.

9. Buena Vista

Buena Vista
Shawneeland
10.0 out of 10, Exceptional, (1 review)
$190 nightly
The price is $191
Dec 8 - Dec 9
Total with taxes and fees
Buena Vista
A cozy cabin-style room with a bed, a couch, a wooden coffee table, a ceiling fan, and a television.

10. Fox Burrow @ Timber Ridge Retreat

Fox Burrow @ Timber Ridge Retreat
Berkeley Springs
10.0 out of 10, Exceptional, (3 reviews)
"The retreat was , what can I say???? AHHHMAZING!! We absolutely loved everything . King sized bed. Decor was adorable and clean, clean, clean. Wood fired hot tub...what a cool concept. Michael, our host was more than accommodating to all our needs and responded to all questions in a timely manner. Although, we didn't bring our four-legged pooch, Stella was nice to know the entire retreat in Pup friendly.We will be back again and more than likely bring friends and family. A.must visit!!!"
United States
Venus R.
$194 nightly
The price is $204
Nov 12 - Nov 13
Total with taxes and fees
Fox Burrow @ Timber Ridge Retreat
A hot tub in front of a wooden cabin with a tree in the background.

11. 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, (15 reviews)
"This tiny house was an absolute dream to stay at! Jen is very attentive to detail- everything from the decor to the thoughtful welcome basket and supplying a feed bucket for the farm animals was perfection. My kids requested our next vacation just be there instead! "
United States
Laura H.
$153 nightly
The price is $170
Nov 16 - Nov 17
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A living room with a sofa, ottoman, lamp, and a mirror.

12. 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.
$246 nightly
The price is $279
Nov 10 - Nov 11
Total with taxes and fees
Morocco Loft 2BR overlooking city walking mall
A house with a deck, surrounded by trees.

13. Forest cabin w/ spacious deck

Forest cabin w/ spacious deck
Gerrardstown
6.0 out of 10, (1 review)
"No pet, several items needed repair. No extra blankets or quilts. Heat wasn't working. Manager communicated well. Finally moved to different rental."
United States
Dorothy P.
$306 nightly
The price is $330
Nov 12 - Nov 13
Total with taxes and fees
Forest cabin w/ spacious deck
Forest Haven is beautiful at night

14. 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.
$306 nightly
The price is $342
Nov 15 - Nov 16
Total with taxes and fees
Forest 2BR chalet w/ hot tub & backyard
A wooden gate in a garden with lush greenery and flowering plants.

15. Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill

Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill
Berkeley Springs
9.0 out of 10, Wonderful, (32 reviews)
"It was refreshing to have a standalone cabin with hot tub ! Nespresso Machine included , what a surprise ."
United States
Alfred
$152 nightly
The price is $170
Nov 11 - Nov 12
Total with taxes and fees
Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill
A spacious living area with a stone wall, a fireplace, a blue sofa, and a kitchen with wooden cabinets and a large window.

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

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
7.8 out of 10, Good, (24 reviews)
"The price was reasonable and the house was clean. The owner communicated very well."
United States
Samantha N.
$299 nightly
The price is $322
Nov 15 - Nov 16
Total with taxes and fees
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
A modern building with a stone facade and a balcony with red chairs.

17. Stone chalet w/ views & hot tub

Stone chalet w/ views & hot tub
Gerrardstown
9.0 out of 10, Wonderful, (45 reviews)
"Lovely, cozy cabin. Hot tub was very relaxing. Overall a wonderful place to stay."
United States
Michael H.
$327 nightly
The price is $353
Dec 7 - Dec 8
Total with taxes and fees
Stone chalet w/ views & hot tub
A house with a well-lit entrance, a small garden, and a gravel driveway.

18. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Martinsburg
9.8 out of 10, Exceptional, (25 reviews)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
$222 nightly
The price is $248
Nov 18 - Nov 19
Total with taxes and fees
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
A hot tub with a wooden deck, a wooden cabin with large windows, and a deck chair.

19. 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.
$312 nightly
The price is $336
Nov 16 - Nov 17
Total with taxes and fees
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

20. Hidden Creekside retreat near 5 national parks, including Harpers Ferry

Hidden Creekside retreat near 5 national parks, including Harpers Ferry
Martinsburg
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful location and property."
United States
Helen F.
$228 nightly
The price is $255
Nov 15 - Nov 16
Total with taxes and fees
Hidden Creekside retreat near 5 national parks, including Harpers Ferry
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

Quality Inn Winchester

Quality Inn Winchester

8/10 Good
"Petit déjeuner disponible dès 6:00AM. Parfait pour reprendre la route tôt. Aussi, tout prêt d’un resto Texas House."
Jacques 1-night trip
Posted 3 hours ago
Quality Inn 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 $164 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.