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Glengary Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Glengary holiday rentals

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

1. 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, (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 "
United States
kayla c.
The price is AU$284
includes taxes & fees
13 Oct - 14 Oct
Enjoy this cabin/tiny home on 24 acres of oak and hickory forest close to Berkeley Springs, WV
A wooden gate in a garden with lush greenery and flowering plants.

2. 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 AU$279
includes taxes & fees
12 Oct - 13 Oct
Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill
A house with a well-lit entrance, a small garden, and a gravel driveway.

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

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Martinsburg
9.8 out of 10, Exceptional, (24 reviews)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
The price is AU$395
includes taxes & fees
12 Oct - 13 Oct
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
A hot tub with two glasses of red wine on a wooden tray.

4. GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV

GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV
Berkeley Springs
9.8 out of 10, Exceptional, (6 reviews)
"Wonderful quiet little getaway spot!! 10/10"
United States
Matthew C.
The price is AU$476
includes taxes & fees
3 Nov - 4 Nov
GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV
A natural setting with a body of water, trees, and a sandy area.

5. Fox Burrow @ Timber Ridge Retreat

Fox Burrow @ Timber Ridge Retreat
Berkeley Springs
10.0 out of 10, Exceptional, (2 reviews)
The price is AU$435
includes taxes & fees
6 Nov - 7 Nov
Fox Burrow @ Timber Ridge Retreat
A spacious living area with a stone wall, a fireplace, a blue sofa, and a kitchen with wooden cabinets and a large window.

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

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
8.0 out of 10, Very good, (23 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
The price is AU$461
includes taxes & fees
8 Oct - 9 Oct
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Grab a towel and relax in the hot tub

7. Stone chalet w/ views & hot tub

Stone chalet w/ views & hot tub
Gerrardstown
9.0 out of 10, Wonderful, (44 reviews)
"Lovely, cozy cabin. Hot tub was very relaxing. Overall a wonderful place to stay."
United States
Michael H.
The price is AU$520
includes taxes & fees
8 Oct - 9 Oct
Stone chalet w/ views & hot tub
Forest Haven is beautiful at night

8. 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 AU$483
includes taxes & fees
3 Nov - 4 Nov
Forest 2BR chalet w/ hot tub & backyard
A wooden deck with a hot tub, outdoor seating, and string lights.

9. Secluded WV Retreat Hot Tub, Fire Pit & Kayaks

Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
Sleepy Hollow
10.0 out of 10, Exceptional, (44 reviews)
"Great place, perfect for a getaway"
United States
Cindy T.
The price is AU$431
includes taxes & fees
20 Oct - 21 Oct
Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
A fire pit surrounded by Adirondack chairs, a wooden deck, and a house in the background.

10. 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)
"Great place"
United States
Orlando A.
The price is AU$452
includes taxes & fees
8 Oct - 9 Oct
River Access Cabin with Hot Tub, Fire Pit & WiFi!
A room with a central island, a ceiling fan, a window with blinds, and a wall-mounted shelf.

11. Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.6 out of 10, Exceptional, (14 reviews)
"Great little place to stay."
United States
Shannon W.
The price is AU$234
includes taxes & fees
12 Oct - 13 Oct
Bring Your Own Boat - Meticulously restored house on the Potomac River
A patio with outdoor furniture, a pool, and a barbecue grill.

12. Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81

Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
Hedgesville
9.0 out of 10, Wonderful, (8 reviews)
"Nice clean property. It was spacious and comfortable. "
United States
Diane G.
The price is AU$165
includes taxes & fees
14 Oct - 15 Oct
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

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

Hidden Creekside retreat near 5 national parks, including Harpers Ferry
Martinsburg
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful location and property."
United States
Helen F.
The price is AU$468
includes taxes & fees
30 Oct - 31 Oct
Hidden Creekside retreat near 5 national parks, including Harpers Ferry
A hot tub on a wooden deck with a red umbrella, surrounded by greenery and a clear sky.

14. 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, (14 reviews)
"Amazing cabin getaway "
United States
Aleks S.
The price is AU$461
includes taxes & fees
28 Oct - 29 Oct
Modern w Mountain Views, Hot Tub, Deck & Fire Pit
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

15. 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 AU$372
includes taxes & fees
12 Oct - 13 Oct
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A small attic bedroom with a sloped ceiling, a single bed, and a window.

16. Primitive Cozy Tiny Cabin with Starlink internet

Primitive Cozy Tiny Cabin with Starlink internet
Great Cacapon
9.4 out of 10, Exceptional, (14 reviews)
"Always a great stay. Peaceful and plenty to explore. We cant wait to come back!"
United States
Anthony A.
The price is AU$287
includes taxes & fees
15 Oct - 16 Oct
Primitive Cozy Tiny Cabin with Starlink internet
A cozy living room with a fireplace, a dining area with a table and chairs, and a large window overlooking a forest.

17. 2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
6.4 out of 10, (12 reviews)
"This place was wonderful. When have stayed at 4 different cabins like this and this was our favorite. The place was cozy and clean. The pantry was well stocked. The fire pit even had a wood fire prepared. The owners were really nice and communicated well. The facilities at the woods were included We live very the location and the hot tub Highly recommend"
United States
Christopher
The price is AU$359
includes taxes & fees
3 Nov - 4 Nov
2-Bedroom cabin Hot tub Fireplace PS5
A cabin with a deck, outdoor seating, and a fire pit.

18. Modern w/Fire Pit, Deck, Grill & Hot Tub

Modern w/Fire Pit, Deck, Grill & Hot Tub
Sleepy Hollow
9.0 out of 10, Wonderful, (21 reviews)
"I enjoyed the property with my niece and nephew. They enjoyed the games provided and the hot tub. Very peaceful. Suggestion from my 9 year old niece, a nite light for the bathroom and kids room . A nice place to chill and relax."
United States
Monika R.
The price is AU$449
includes taxes & fees
12 Oct - 13 Oct
Modern w/Fire Pit, Deck, Grill & Hot Tub
A living room with a TV, two sofas, a coffee table, and a large plant.

19. 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 AU$667
includes taxes & fees
2 Nov - 3 Nov
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
A cozy living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

20. MID-CENTURY MODERN A-FRAME - HOT TUB/FIREPIT IN WOODS

MID-CENTURY MODERN A-FRAME - HOT TUB/FIREPIT IN WOODS
The Woods
9.8 out of 10, Exceptional, (38 reviews)
"Great stay."
United States
Amy M.
MID-CENTURY MODERN A-FRAME - HOT TUB/FIREPIT IN WOODS
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 Glengary Hotel Reviews

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"The mattress was excellent. I woke up refreshed without a back ache which I came in with due to the long car ride. My room was quiet, and clean. My only complaint is wondering why there is such a strong smell of air deodorizer throughout the hotel. It hits you as you walk in the lobby. The smell lingered on my clothes and inside my suitcases through the next day. I prefer fresh air, not artificial air freshener scents. I don’t believe they are healthy."
Darlyne 1-night trip
Posted 22 hours ago
TRU By Hilton Winchester

Find out more about Glengary

Everything you need to know about Glengary 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 Glengary holiday rental for you. At Expedia, you can take your pick from private holiday 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 Glengary holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Glengary holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Glengary. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Glengary 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 Glengary holiday rentals we have selected for you start as low as AU$279 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Glengary rentals

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

Yes, there are holiday rentals close to the most popular sights in Glengary, 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 Glengary has to offer?

A-Frame Mountain Retreat: This holiday home rental outside of Glengary offers a patio, a selection of games and a BBQ 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 holiday with amenities such as 1 hot tub.

What’s there to see and do in Glengary?

While exploring the area, visit family-friendly sights like Shenandoah Valley Discovery Museum, or get outside and enjoy nature at Cacapon Resort State Park. Peacemaker National Training Center and Sleepy Creek Wildlife Management Area are a couple of places you'll find in the wider area.

What’s a holiday rental in Glengary like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Glengary. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.