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Gainesboro Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Gainesboro holiday rentals

Smart TV, fireplace, video games, DVD player

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, (84 reviews)
"The cabin was very cozy and we loved how rustic it felt. "
United States
Ryan
The price is HK$974
HK$2,628 total
includes taxes & fees
29 Jul - 30 Jul
Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.
Living area

Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is HK$1,256
HK$2,356 total
includes taxes & fees
23 Jul - 24 Jul
Morocco Loft 2BR overlooking city walking mall
Private kitchen

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, (7 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is HK$1,529
HK$1,981 total
includes taxes & fees
23 Jul - 24 Jul
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Coffee/tea maker, fridge, microwave, oven

Cameron Grace Brand New 1BR 1BA apt downtown Winchester

Cameron Grace Brand New 1BR 1BA apt downtown Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Very enjoyable stay right in historical Winchester. We enjoyed walking to a German restaurant for dinner and rested well. "
United States
Brad E.
The price is HK$1,215
HK$2,034 total
includes taxes & fees
27 Jul - 28 Jul
Cameron Grace Brand New 1BR 1BA apt downtown Winchester
TV

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, (1 review)
The price is HK$1,160
HK$1,981 total
includes taxes & fees
19 Aug - 20 Aug
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Terrace/patio

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 HK$1,306
HK$2,616 total
includes taxes & fees
9 Aug - 10 Aug
Forest 2BR chalet w/ hot tub & backyard
Smart TV, fireplace

Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.8 out of 10, Exceptional, (7 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is HK$1,741
HK$3,074 total
includes taxes & fees
23 Jul - 24 Jul
Scarborough Fair walk to downtown two story apt
Exterior

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)
"Nice house in a good central location. "
United States
Mitchell V.
The price is HK$1,553
HK$2,736 total
includes taxes & fees
2 Aug - 3 Aug
Cameron Charmer pristine downtown apt with double master suites
Terrace/patio

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 HK$1,314
HK$2,638 total
includes taxes & fees
10 Aug - 11 Aug
Stone chalet w/ views & hot tub
Smart TV, books

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
8.8 out of 10, Excellent, (5 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 HK$1,082
HK$1,803 total
includes taxes & fees
19 Aug - 20 Aug
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Smart TV

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, (17 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 HK$1,451
HK$2,612 total
includes taxes & fees
23 Jul - 24 Jul
Nostalgia Lane in the heart of the city
Terrace/patio

Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
9.6 out of 10, Exceptional, (8 reviews)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
United States
Anonymous traveller
The price is HK$784
HK$1,377 total
includes taxes & fees
26 Jul - 27 Jul
Cozy English Basement Apt quiet but close to downtown
Terrace/patio

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 HK$1,200
HK$2,302 total
includes taxes & fees
28 Jul - 29 Jul
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
Outdoor dining

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

Modern w Mountain Views, Hot Tub, Deck & Fire Pit
Berkeley Springs
9.6 out of 10, Exceptional, (12 reviews)
"Beautiful get away"
United States
Brett R.
The price is HK$1,305
HK$2,340 total
includes taxes & fees
5 Aug - 6 Aug
Modern w Mountain Views, Hot Tub, Deck & Fire Pit
TV, fireplace, offices

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
8.0 out of 10, Very good, (17 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
The price is HK$1,068
HK$2,437 total
includes taxes & fees
28 Jul - 29 Jul
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Terrace/patio

Mountain cabin w/ hot tub & deck

Mountain cabin w/ hot tub & deck
Berkeley Springs
9.4 out of 10, Exceptional, (38 reviews)
"It’s a great place to stay if you want to get away from the big city noises but like the notes say it if about 20 minutes from everything. But we enjoyed the state park and Berkeley Springs. I would recommend going to the bath house."
United States
Christine L.
The price is HK$3,515
HK$5,267 total
includes taxes & fees
25 Jul - 26 Jul
Mountain cabin w/ hot tub & deck
Terrace/patio

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
9.8 out of 10, Exceptional, (10 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 HK$1,137
HK$1,440 total
includes taxes & fees
19 Aug - 20 Aug
Luxury tiny home farm stay on historic property with hot tub in Stephens City
TV, fireplace

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, (8 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.
The price is HK$1,446
HK$3,000 total
includes taxes & fees
3 Aug - 4 Aug
Upscale w Fireplace, Fire Pit, Games in Gated Comm
Private kitchen

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
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Dining

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 HK$1,607
HK$2,905 total
includes taxes & fees
23 Jul - 24 Jul
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"We always stay here on our way to Massachusetts and on the way home, The rooms and bathrooms are very clean, beds are great with lovely sheets, towels are thick, convenient to restaurants, and the staff is friendly and welcoming. We love Roy who remembered us when we came back through. Breakfast was good as far as my husband and grandkids are concerned with waffles, bagels, and cereal. We will be back."
Patsy 1-night trip
Posted 10 hours ago
Comfort Inn & Suites Winchester

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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Look no further and take a look at our great range of rental properties in Gainesboro!

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?

Beautiful Log Chalet/Cabin with Hot Tub: This holiday home rental outside of Gainesboro is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Mackintosh Fruit Farm. In the wider area, you’ll find Rock Harbor Golf Course and Museum of the Shenandoah Valley.

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.