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Gainesboro Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Gainesboro vacation rentals

Terrace/patio

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
The price is ￥17,906
￥39,071 total
includes taxes & fees
Sep 1 - Sep 2
Large Glamper w/ Hot Tub and full bathroom-sleep 6
Living area

2. Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.

Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.
Cross Junction
9.6 out of 10, Exceptional, (86 reviews)
"The best, peaceful, fun, ATV wheeling, target practice, grilling, great kitchen supplies and plenty of space for the family Would stay again"
United States
Lisa G.
The price is ￥17,953
￥51,066 total
includes taxes & fees
Aug 26 - Aug 27
Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.
Beach

3. 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, (2 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.
The price is ￥10,703
￥29,256 total
includes taxes & fees
Aug 20 - Aug 21
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
Beach

4. Fox Burrow @ Timber Ridge Retreat

Fox Burrow @ Timber Ridge Retreat
Berkeley Springs
10.0 out of 10, Exceptional, (2 reviews)
The price is ￥14,054
￥35,299 total
includes taxes & fees
Aug 20 - Aug 21
Fox Burrow @ Timber Ridge Retreat
Interior

5. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very Good, (2 reviews)
"Small but appropriately priced."
United States
John M.
The price is ￥17,536
￥30,886 total
includes taxes & fees
Aug 25 - Aug 26
Rosamond nice downtown studio apt
Living area

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
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.
The price is ￥23,618
￥41,947 total
includes taxes & fees
Aug 31 - Sep 1
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Terrace/patio

7. Stone chalet w/ views & hot tub

Stone chalet w/ views & hot tub
Gerrardstown
9.0 out of 10, Wonderful, (43 reviews)
"Lovely, cozy cabin. Hot tub was very relaxing. Overall a wonderful place to stay."
United States
Michael H.
The price is ￥25,112
￥52,354 total
includes taxes & fees
Sep 3 - Sep 4
Stone chalet w/ views & hot tub
Living area

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

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
8.2 out of 10, Very Good, (19 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
The price is ￥21,719
￥49,876 total
includes taxes & fees
Aug 23 - Aug 24
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Exterior detail

9. 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.
The price is ￥17,536
￥31,971 total
includes taxes & fees
Sep 10 - Sep 11
The Stock Exchange downtown 3rd floor studio apt
Property grounds

10. River Access Cabin with Hot Tub, Fire Pit & WiFi!

River Access Cabin with Hot Tub, Fire Pit & WiFi!
Berkeley Springs
9.2 out of 10, Wonderful, (35 reviews)
"We had a great stay! The cabin was clean and had just enough space for our family. We absolutely loved the setting with frequent wildlife sightings and great spaces to relax and enjoy the mountain views. The host was attentive and checked in often to give inspiration for restaurants and activities nearby. Berkeley Springs is close enough to enjoy the town but far enough away to give you a true feeling of peace out in the woods. We loved our stay and are thankful to have found this little gem!"
United States
Jennifer S.
The price is ￥23,683
￥48,648 total
includes taxes & fees
Aug 20 - Aug 21
River Access Cabin with Hot Tub, Fire Pit & WiFi!
Private kitchen

11. 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 ￥15,623
￥44,535 total
includes taxes & fees
Aug 20 - Aug 21
The Queen of Winchester Three Bedroom with Upper Level Deck
Interior

12. Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.6 out of 10, Exceptional, (9 reviews)
"It was decorated very cute and the bed was comfortable. Very close to shops and restaurants.We had to drive around the block and get out to find the location because you park and enter through the back door.It’s very close to the train stain but was only interrupted by an early morning train once."
United States
Brenda H.
The price is ￥20,725
￥35,041 total
includes taxes & fees
Sep 1 - Sep 2
Pretty Little Apt by the Train II
Living area

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.
The price is ￥22,000
￥37,751 total
includes taxes & fees
Sep 17 - Sep 18
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Outdoor spa tub

14. GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV

GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV
Berkeley Springs
9.4 out of 10, Exceptional, (3 reviews)
"Pet friendly, clean, spacious, great communication, all the amenities we could ask for, this place was perfect for our little family get away! The kids loved the glamping dome and we all loved the hot tub! We will keep this place in mind for sure next time we’re in the area! Thank you Priya and Gauthaman!"
United States
Stephanie H.
The price is ￥14,684
￥52,160 total
includes taxes & fees
Aug 20 - Aug 21
GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV
Terrace/patio

15. 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 ￥24,065
￥46,799 total
includes taxes & fees
Aug 23 - Aug 24
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
Private kitchen

16. Buena Vista

Buena Vista
Shawneeland
The price is ￥14,203
￥34,779 total
includes taxes & fees
Sep 9 - Sep 10
Buena Vista
Terrace/patio

17. 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 ￥26,245
￥53,509 total
includes taxes & fees
Aug 20 - Aug 21
Forest 2BR chalet w/ hot tub & backyard
Private kitchen

18. 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, (8 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is ￥31,087
￥40,099 total
includes taxes & fees
Sep 17 - Sep 18
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Outdoor dining

19. 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, (13 reviews)
"Amazing cabin getaway "
United States
Aleks S.
The price is ￥23,683
￥44,570 total
includes taxes & fees
Sep 7 - Sep 8
Modern w Mountain Views, Hot Tub, Deck & Fire Pit
Terrace/patio

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, (11 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 ￥23,116
￥29,455 total
includes taxes & fees
Aug 24 - Aug 25
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

Hampton Inn Martinsburg

Hampton Inn Martinsburg

10/10 Excellent
"The rooms were spacious. The staff was very kind and the dining area was well attended. We had a large party of people staying for the weekend and each person was happy with their accommodations . Everything was clean and neat."
Leonard 3-night trip
Posted 3 hours ago
Hampton Inn Martinsburg

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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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?

Secluded Mountain Cabin with Spectacular Views- Hiker's Dream: Visitors like this Gainesboro vacation home rental. It is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Rock Harbor Golf Course and Museum of the Shenandoah Valley.

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.