Gainesboro Vacation Rentals
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Our top choices for Gainesboro vacation rentals
1. The Queen of Winchester Three Bedroom with Upper Level Deck
The Queen of Winchester Three Bedroom with Upper Level DeckWinchester
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."
Chris C.
The price is CA $106
CA $334 total
includes taxes & fees
Nov 30 - Dec 1
2. Rosamond nice downtown studio apt
Rosamond nice downtown studio aptWinchester 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"
Jameson D.
The price is CA $155
CA $259 total
includes taxes & fees
Nov 12 - Nov 13
3. 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."
Timothy B.
The price is CA $209
CA $354 total
includes taxes & fees
Nov 19 - Nov 20
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, WVBerkeley 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 "
kayla c.
The price is CA $83
CA $239 total
includes taxes & fees
Nov 9 - Nov 10
5. Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mallWinchester 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!"
Leslie L.
The price is CA $195
CA $319 total
includes taxes & fees
Nov 15 - Nov 16
6. 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 CityStephens 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! "
Laura H.
The price is CA $203
CA $245 total
includes taxes & fees
Dec 7 - Dec 8
7. Morocco Loft 2BR overlooking city walking mall
Morocco Loft 2BR overlooking city walking mallOld Town Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Great property with all the comforts of home"
Kristen R.
The price is CA $250
CA $437 total
includes taxes & fees
Nov 17 - Nov 18
8. Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill
Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, GrillBerkeley 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 ."
Alfred
The price is CA $88
CA $244 total
includes taxes & fees
Nov 9 - Nov 10
9. The Stock Exchange downtown 3rd floor studio apt
The Stock Exchange downtown 3rd floor studio aptWinchester Historic District
7.0 out of 10, Good, (2 reviews)
"Everything went smoothly. Easy stay. Clean. Small efficiency with futon for bed."
Greg A.
The price is CA $155
CA $267 total
includes taxes & fees
Nov 12 - Nov 13
10. Fox Burrow @ Timber Ridge Retreat
Fox Burrow @ Timber Ridge RetreatBerkeley 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!!!"
Venus R.
The price is CA $119
CA $298 total
includes taxes & fees
Nov 12 - Nov 13
11. Forest cabin w/ spacious deck
Forest cabin w/ spacious deckGerrardstown
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."
Dorothy P.
The price is CA $223
CA $482 total
includes taxes & fees
Nov 12 - Nov 13
12. Forest 2BR chalet w/ hot tub & backyard
Forest 2BR chalet w/ hot tub & backyardGerrardstown
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"
John Z.
The price is CA $242
CA $505 total
includes taxes & fees
Nov 9 - Nov 10
13. Stone chalet w/ views & hot tub
Stone chalet w/ views & hot tubGerrardstown
9.0 out of 10, Wonderful, (45 reviews)
"Lovely, cozy cabin. Hot tub was very relaxing. Overall a wonderful place to stay."
Michael H.
The price is CA $253
CA $504 total
includes taxes & fees
Nov 30 - Dec 1
14. Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Fireplace, Wraparound Deck, & WiFi at Chalet CabinGerrardstown
7.8 out of 10, Good, (24 reviews)
"The price was reasonable and the house was clean. The owner communicated very well."
Samantha N.
The price is CA $203
CA $476 total
includes taxes & fees
Nov 15 - Nov 16
15. GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV
GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WVBerkeley Springs
9.8 out of 10, Exceptional, (6 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!"
Stephanie H.
The price is CA $155
CA $450 total
includes taxes & fees
Nov 10 - Nov 11
16. 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, (36 reviews)
"Great place"
Orlando A.
The price is CA $223
CA $466 total
includes taxes & fees
Nov 15 - Nov 16
17. Cameron Charmer pristine downtown apt with double master suites
Cameron Charmer pristine downtown apt with double master suitesWinchester
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."
Carolyn F.
The price is CA $280
CA $475 total
includes taxes & fees
Nov 9 - Nov 10
18. Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Magnolia Winds 3-bedroom apartment in charming Winchester with cool ACOld Town Winchester
10.0 out of 10, Exceptional, (17 reviews)
"Perfect location and unique and charming house."
Heather O.
19. Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-FriendlyGerrardstown
9.0 out of 10, Wonderful, (12 reviews)
"We had a fabulous time and highly recommend this rental."
Amber H.
The price is CA $246
CA $493 total
includes taxes & fees
Nov 16 - Nov 17
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
The George Washington Hotel, A Wyndham Grand Hotel
10/10 Excellent
Find out more about Gainesboro
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.
