Gainesboro Vacation Rentals from CA $239: Short-Term Rentals for 2026

Q: 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

Old Town Winchester

A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

2. The Queen of Winchester Three Bedroom with Upper Level Deck

Winchester

Chris C.

CA $347 total

includes taxes & fees

Nov 30 - Dec 1

A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

3. Rosamond nice downtown studio apt

Winchester Historic District

Jameson D.

CA $259 total

includes taxes & fees

Nov 12 - Nov 13

A lake with clear water, surrounded by trees and a sandy shore.

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

Berkeley Springs

kayla c.

CA $239 total

includes taxes & fees

Nov 11 - Nov 12

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

Winchester

CA $363 total

includes taxes & fees

Nov 12 - Nov 13

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!

Winchester Historic District

Timothy B.

CA $354 total

includes taxes & fees

Nov 19 - Nov 20

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

Winchester Historic District

Leslie L.

CA $304 total

includes taxes & fees

Nov 15 - Nov 16

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

Winchester Historic District

Greg A.

CA $267 total

includes taxes & fees

Nov 12 - Nov 13

A compact kitchen with a central island, wooden cabinets, a microwave, and a refrigerator.

9. Buena Vista

Shawneeland

CA $268 total

includes taxes & fees

Dec 8 - Dec 9

A natural setting with a body of water, trees, and a sandy area.

10. Fox Burrow @ Timber Ridge Retreat

Berkeley Springs

"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.

CA $296 total

includes taxes & fees

Nov 15 - Nov 16

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

Stephens City

Laura H.

CA $237 total

includes taxes & fees

Nov 17 - Nov 18

A living room with a sofa, ottoman, lamp, and a mirror.

12. Morocco Loft 2BR overlooking city walking mall

Old Town Winchester

Kristen R.

CA $410 total

includes taxes & fees

Nov 12 - Nov 13

A house with a deck, surrounded by trees.

13. Forest cabin w/ spacious deck

Gerrardstown

Dorothy P.

CA $461 total

includes taxes & fees

Nov 15 - Nov 16

14. Forest 2BR chalet w/ hot tub & backyard

Gerrardstown

John Z.

CA $482 total

includes taxes & fees

Nov 15 - Nov 16

A wooden gate in a garden with lush greenery and flowering plants.

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

Berkeley Springs

Alfred

CA $248 total

includes taxes & fees

Nov 11 - Nov 12

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

Gerrardstown

Samantha N.

CA $454 total

includes taxes & fees

Nov 15 - Nov 16

A modern building with a stone facade and a balcony with red chairs.

17. Stone chalet w/ views & hot tub

Gerrardstown

Michael H.

CA $504 total

includes taxes & fees

Nov 30 - Dec 1

A glass-enclosed shower with white tiles, a towel rack with folded towels, and a metal shelf unit.

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

Martinsburg

Arnold A.

CA $360 total

includes taxes & fees

Nov 18 - Nov 19

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

Gerrardstown

Amber H.

CA $493 total

includes taxes & fees

Nov 16 - Nov 17

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

Martinsburg

Helen F.

CA $369 total

includes taxes & fees

Nov 15 - Nov 16

View all properties

Find vacation rentals that suit your style

Apartments

Cabins

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Gainesboro Hotel Reviews

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent

"Nice clean room and very nice staff. The breakfast spread was pretty good too."

Hillbrook Inn

8/10 Good

"Most importantly, the cleanliness of the room and the staff were absolutely excellent. We stayed in the Hawthorn North Suite. Room: I would have enjoyed a firmer mattress. My wife had no complaints, but I had to place a pillow under my legs for back comfort. The soaking tub was quite nice; however, only one person could fit in the tub and there were no built-in water or air jets. Cottage: There was a beautiful, in-tune piano to which we had access. There was also a pool table in the basement that was not warped! Breakfast was quite tasty...would have loved more variety. Unfortunately, we did not take the opportunity to enjoy the on-site restaurant for dinner nor its on-site spa. We also did not visit any wineries. There were restaurants, small shopping areas, and the Harpers Ferry National Historical Park nearby."

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gainesboro vacation rentals we have selected for you start as low as CA $239 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 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gainesboro vacation rentals

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

2. The Queen of Winchester Three Bedroom with Upper Level Deck

3. Rosamond nice downtown studio apt

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

5. Executive Suites

6. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

7. Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

8. The Stock Exchange downtown 3rd floor studio apt

9. Buena Vista

10. Fox Burrow @ Timber Ridge Retreat

11. Luxury tiny home farm stay on historic property with hot tub in Stephens City

12. Morocco Loft 2BR overlooking city walking mall

13. Forest cabin w/ spacious deck

14. Forest 2BR chalet w/ hot tub & backyard

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

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

17. Stone chalet w/ views & hot tub

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

19. Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly

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

Find vacation rentals that suit your style

Top Gainesboro Hotel Reviews

Fairfield Inn & Suites by Marriott Winchester

Comfort Inn & Suites Winchester

Quality Inn Winchester

Spark by Hilton Winchester

Days Inn by Wyndham Winchester

Hilton Garden Inn Martinsburg

The George Washington Hotel, A Wyndham Grand Hotel

Hillbrook Inn

Find out more about Gainesboro

Frequently asked questions

Go further with the Expedia app