Gerrardstown Vacation Rentals from $195: Search Short-Term Rentals

Q: What's the top vacation rental in Gerrardstown?

A-Frame Mountain Retreat : Visitors like this Gerrardstown 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.

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Our top choices for Gerrardstown vacation rentals

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

Gerrardstown

John Z.

$305 nightly

Oct 22 - Oct 23

Total with taxes and fees

2. Stone chalet w/ views & hot tub

Gerrardstown

Michael H.

$341 nightly

Oct 19 - Oct 20

Total with taxes and fees

A living room with a TV, two sofas, a coffee table, and a large plant.

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

Gerrardstown

Amber H.

$421 nightly

Nov 2 - Nov 3

Total with taxes and fees

A spacious living area with a stone wall, a fireplace, a blue sofa, and a kitchen with wooden cabinets and a large window.

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

Gerrardstown

Scott K.

$299 nightly

Oct 13 - Oct 14

Total with taxes and fees

5. Stone Cabin with Amazing Views, Hot Tub, Fire Pit and Game Room Perfect for Your Gerrardstown, WV Getaway

Gerrardstown

$490 nightly

Oct 19 - Oct 20

Total with taxes and fees

6. Forest Haven Chalet Cabin

Gerrardstown

$430 nightly

Nov 2 - Nov 3

Total with taxes and fees

A dining area with a wooden table, black chairs, and a bench. There is a painting on the wall and a kitchen in the background.

7. Secluded Chalet-Cabin with Hot Tub, Fire Pit, Deck and Grill - the Perfect Place to Relax in Gerrardstown, WV

Gerrardstown

$577 nightly

Nov 2 - Nov 3

Total with taxes and fees

8. Fantastic Cabin with Barbecue and Hot-tub in Gerrardstown, West Virginia

Gerrardstown

$434 nightly

Nov 2 - Nov 3

Total with taxes and fees

9. Enchanted Mountain Cabin Retreat with Woodland Serenity near Sleepy Creek Lake West Virginia

Gerrardstown

$434 nightly

Oct 14 - Oct 15

Total with taxes and fees

10. Forest cabin w/ hot tub, deck & huge yard

Gerrardstown

"The house has real potential, but also has real problems. It needs some maintenance in a major way. The toilet won’t flush. The faucet in the bathtub fell off. The grill had not been cleaned in so long that it broke out into a fire. When communicated these problems with the host, the response was I’m sorry for the inconvenience. We will have our handyman fix it after you leave. Frankly, I wanted it fixed while we were there. They also did not provide the necessary materials for cleaning dishes....

Heather H.

$303 nightly

Nov 2 - Nov 3

Total with taxes and fees

11. Forest cabin w/ spacious deck

Gerrardstown

Dorothy P.

$303 nightly

Oct 14 - Oct 15

Total with taxes and fees

A modern kitchen with dark wood cabinets, a central island, stainless steel appliances, and a skylight.

12. Emerald in Berkeley Springs, WV

Berkeley Springs

Elizabeth K.

$571 nightly

Oct 31 - Nov 1

Total with taxes and fees

A hot tub on a wooden deck with a red umbrella, surrounded by greenery and a clear sky.

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

Berkeley Springs

Brett R.

$269 nightly

Nov 3 - Nov 4

Total with taxes and fees

A log cabin interior with a fireplace, a television, a sofa, and a dining area.

14. Fox Hollow | Romantic Wooded Retreat w/ Fire Pit & Hot Tub

Berkeley Springs

S S P.

$745 nightly

Nov 8 - Nov 9

Total with taxes and fees

A spacious living room with a wooden floor, a dining area with a table and chairs, a yellow armchair, a black spiral staircase, and large windows offering a view of the outdoors.

15. Cabin w Fire Pit, Hot Tub, Screened Porch & More

The Woods

Katlin M.

$374 nightly

Oct 19 - Oct 20

Total with taxes and fees

A cozy living room with a fireplace, a dining area with a table and chairs, and a large window overlooking a forest.

16. 2-Bedroom cabin Hot tub Fireplace PS5

The Woods

Christopher

$269 nightly

Nov 2 - Nov 3

Total with taxes and fees

A wooden cabin with a triangular roof, a front door, and a small porch with a bench.

17. Great Views! A-Frame w Hot Tub, Grill & Fire Pit

Berkeley Springs

Joe W.

$325 nightly

Oct 21 - Oct 22

Total with taxes and fees

A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

18. ❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown

Dennis C.

$96 nightly

Oct 25 - Oct 26

Total with taxes and fees

A fire pit surrounded by Adirondack chairs, a wooden deck, and a house in the background.

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

Berkeley Springs

Orlando A.

$291 nightly

Oct 14 - Oct 15

Total with taxes and fees

A spacious living area with a wooden ceiling, a fireplace, a sofa, and a dining table with a glass top.

20. Sleepy Creek Getaway! Hot tub & Sauna

Berkeley Springs

April W.

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Top Gerrardstown Hotel Reviews

Spark by Hilton Winchester

10/10 Excellent

"The place was excellent. Staff were amazing and room was beautiful. Would def stay here again."

Travelodge by Wyndham Winchester

8/10 Good

"Room was spacious and clean, great with my dog. Breakfast was continental, with waffles or toast, cereal, or yogurt. We were in an outside room for convenience to take dog outside, but there was hardly any grass on that end of the hotel for her to 'go'. The grassy area was on the other end of the hotel. The front desk staff was helpful and accommodating."

Comfort Inn & Suites Winchester

10/10 Excellent

"It’s in a very nice shopping plaza next to a grocery store restaurant in movie theater, so it was perfect for me. It’s been relatively recently renovated, but besides that it was very very clean and the staff was excellent from front desk to the night audit and even the woman who did breakfast was really lovely and the door to breakfast prep was open so I could see how clean it was in there."

Find out more about Gerrardstown

Everything you need to know about Gerrardstown 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 Gerrardstown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Gerrardstown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gerrardstown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gerrardstown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Gerrardstown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $195 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Gerrardstown rentals

At Expedia, we put the best Gerrardstown 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 Gerrardstown 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 Gerrardstown 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 Gerrardstown. 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 Gerrardstown?

Yes, we have vacation rentals close to top points of interest in Gerrardstown, or you can go with a secluded option if you're looking for relaxation.

What's the top vacation rental in Gerrardstown?

A-Frame Mountain Retreat: Visitors like this Gerrardstown 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 can I see and do in Gerrardstown?

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. While here, Gerrardstown Historic District and Mill Creek Historic District are other places worth a visit.

What are vacation rentals like in Gerrardstown?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Gerrardstown. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for family gatherings.

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Check prices for these dates

Our top choices for Gerrardstown vacation rentals

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

2. Stone chalet w/ views & hot tub

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

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

5. Stone Cabin with Amazing Views, Hot Tub, Fire Pit and Game Room Perfect for Your Gerrardstown, WV Getaway

6. Forest Haven Chalet Cabin

7. Secluded Chalet-Cabin with Hot Tub, Fire Pit, Deck and Grill - the Perfect Place to Relax in Gerrardstown, WV

8. Fantastic Cabin with Barbecue and Hot-tub in Gerrardstown, West Virginia

9. Enchanted Mountain Cabin Retreat with Woodland Serenity near Sleepy Creek Lake West Virginia

10. Forest cabin w/ hot tub, deck & huge yard

11. Forest cabin w/ spacious deck

12. Emerald in Berkeley Springs, WV

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

14. Fox Hollow | Romantic Wooded Retreat w/ Fire Pit & Hot Tub

15. Cabin w Fire Pit, Hot Tub, Screened Porch & More

16. 2-Bedroom cabin Hot tub Fireplace PS5

17. Great Views! A-Frame w Hot Tub, Grill & Fire Pit

18. ❤️ Secluded 1940s Romantic Tiny House on the River

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

20. Sleepy Creek Getaway! Hot tub & Sauna

Find vacation rentals that suit your style

Top Gerrardstown Hotel Reviews

Spark by Hilton Winchester

Microtel Inn & Suites by Wyndham Winchester

Super 8 by Wyndham Hancock MD

Tru By Hilton Martinsburg

Country Inn & Suites by Radisson, Winchester, VA

Travelodge by Wyndham Winchester

TRU By Hilton Winchester

Days Inn by Wyndham Winchester

Comfort Inn & Suites Winchester

Find out more about Gerrardstown

Frequently asked questions

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