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Our top choices for Gainesboro holiday rentals

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 £183
includes taxes & fees
15 Sept - 16 Sept
Large Glamper w/ Hot Tub and full bathroom-sleep 6

2. Buena Vista

Buena Vista
Shawneeland
10.0 out of 10, Exceptional, (1 review)
The price is £160
includes taxes & fees
9 Sept - 10 Sept
Buena Vista

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
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 £198
includes taxes & fees
8 Sept - 9 Sept
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

4. 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)
"Perfect location for walking around Old Town Winchester!"
United States
Clint B.
The price is £185
includes taxes & fees
12 Sept - 13 Sept
Pretty Little Apt by the Train II

5. 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 £178
includes taxes & fees
8 Sept - 9 Sept
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

6. 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 £145
includes taxes & fees
9 Sept - 10 Sept
Rosamond nice downtown studio apt

7. 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 £199
includes taxes & fees
8 Sept - 9 Sept
The Queen of Winchester Three Bedroom with Upper Level Deck

8. Fox Burrow @ Timber Ridge Retreat

Fox Burrow @ Timber Ridge Retreat
Berkeley Springs
10.0 out of 10, Exceptional, (2 reviews)
The price is £162
includes taxes & fees
8 Sept - 9 Sept
Fox Burrow @ Timber Ridge Retreat

9. 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, (28 reviews)
"Clean cozy room, functional kitchen and the host was communicative! "
United States
Carrie S.
The price is £138
includes taxes & fees
8 Sept - 9 Sept
Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill

10. 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 £225
includes taxes & fees
21 Sept - 22 Sept
Stone chalet w/ views & hot tub

11. 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 £152
includes taxes & fees
7 Oct - 8 Oct
The Stock Exchange downtown 3rd floor studio apt

12. 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 £211
includes taxes & fees
10 Sept - 11 Sept
Modern w Mountain Views, Hot Tub, Deck & Fire Pit

13. The Blue Door steps from Handley Library

The Blue Door steps from Handley Library
Old Town Winchester
5.4 out of 10, (3 reviews)
"Perfect. Met all expectations. Small but Great."
United States
derric3k
The price is £146
includes taxes & fees
30 Sept - 1 Oct
The Blue Door steps from Handley Library

14. 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 £183
includes taxes & fees
8 Sept - 9 Sept
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

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

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
7.8 out of 10, Good, (20 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
The price is £232
includes taxes & fees
13 Sept - 14 Sept
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

16. 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 £138
includes taxes & fees
10 Sept - 11 Sept
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV

17. 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.
The price is £249
includes taxes & fees
8 Sept - 9 Sept
Nostalgia Lane in the heart of the city

18. 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 £239
includes taxes & fees
4 Oct - 5 Oct
River Access Cabin with Hot Tub, Fire Pit & WiFi!

19. 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 £246
includes taxes & fees
8 Sept - 9 Sept
Forest 2BR chalet w/ hot tub & backyard

20. 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.
The price is £240
includes taxes & fees
22 Sept - 23 Sept
Morocco Loft 2BR overlooking city walking mall
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

Find out more about Gainesboro

Everything you need to know about Gainesboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gainesboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Gainesboro holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gainesboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gainesboro holiday rentals we have selected for you start as low as £162 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Gainesboro rentals

At Expedia, we put the best Gainesboro holiday 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 holiday.

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 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 Cacapon Resort State Park. 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.