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Glengary Holiday Rentals

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50 rentals in Glengary.
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Hilltop Gerrardstown Retreat w/ Multi-Tiered Deck!, holiday rental in Glengary

Hilltop Gerrardstown Retreat w/ Multi-Tiered Deck!

3 bedrooms
3 bathrooms
Sleeps 8
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A luxurious cabin quietly tucked away in the woods of Berkeley Springs, holiday rental in Glengary

A luxurious cabin quietly tucked away in the woods of Berkeley Springs

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded, Convenient, WiFi, Near Cacapon State Park, holiday rental in Glengary

Secluded, Convenient, WiFi, Near Cacapon State Park

5 bedrooms
4 bathrooms
Sleeps 15
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Upscale private getaway near Sleepy Creek, holiday rental in Glengary

Upscale private getaway near Sleepy Creek

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spectacular couples retreat, private wooded location, pet friendly, WiFi, holiday rental in Glengary

Spectacular couples retreat, private wooded location, pet friendly, WiFi

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities, holiday rental in Glengary

Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Log Cabin Built in 2015 Located at the Base of Sleepy Creek Mountain, holiday rental in Glengary

Log Cabin Built in 2015 Located at the Base of Sleepy Creek Mountain

4 bedrooms
2 bathrooms
Sleeps 8
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Cozy Modern Private Cabin with Hot Tub Nestled In Excusive Coolfont Mountainside, holiday rental in Glengary

Cozy Modern Private Cabin with Hot Tub Nestled In Excusive Coolfont Mountainside

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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City Charmer near Historic OldTown Winchester., holiday rental in Glengary

City Charmer near Historic OldTown Winchester.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Mountain View, Secluded Romantic, Family Friendly WiFi, holiday rental in Glengary

Beautiful Mountain View, Secluded Romantic, Family Friendly WiFi

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Townhome At The Woods Resort Golf, Spa, Swimming, Tennis, and Hiking, holiday rental in Glengary

Cozy Townhome At The Woods Resort Golf, Spa, Swimming, Tennis, and Hiking

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cozy A frame Cabin in the beautiful Woods Golf Resort, holiday rental in Glengary

Cozy A frame Cabin in the beautiful Woods Golf Resort

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cabin w Hot Tub, River/Kayak, WiFi, & Fire Pit!, holiday rental in Glengary

Cabin w Hot Tub, River/Kayak, WiFi, & Fire Pit!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Colonial Getaway Near Old Town Historic Winchester, holiday rental in Glengary

Colonial Getaway Near Old Town Historic Winchester

3 bedrooms
3 bathrooms
Sleeps 8
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Downtown Berkeley Springs, holiday rental in Glengary

Downtown Berkeley Springs

2 bedrooms
1 bathroom
Sleeps 4
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Right on the river., holiday rental in Glengary

Right on the river.

4 bedrooms
3 bathrooms
Sleeps 11
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Beautiful Victorian built in 1912 “The Brookside Manor” in Berkeley Springs WV, holiday rental in Glengary

Beautiful Victorian built in 1912 “The Brookside Manor” in Berkeley Springs WV

3 bedrooms
5 bathrooms
Sleeps 7
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Ruby Summit Point - Your Home at the Track, holiday rental in Glengary

Ruby Summit Point - Your Home at the Track

3 bedrooms
1 bathroom
Sleeps 6
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Quiet Renovated Historic Condo Above Abolitionist Ale Works w/ Washer Dryer #301, holiday rental in Glengary

Quiet Renovated Historic Condo Above Abolitionist Ale Works w/ Washer Dryer #301

2 bedrooms
1 bathroom
Sleeps 5
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Secluded Pet-Friendly High-Tech Log Cabin in the Woods, holiday rental in Glengary

Secluded Pet-Friendly High-Tech Log Cabin in the Woods

3 bedrooms
2 bathrooms
Sleeps 6
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New modern Log Cabin. Private wooded surroundings., holiday rental in Glengary

New modern Log Cabin. Private wooded surroundings.

3 bedrooms
2 bathrooms
Sleeps 8
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Rock Spring Retreat, holiday rental in Glengary

Rock Spring Retreat

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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1200 SqFt Condo Above Abolitionist Ale Works Charles Town w/ Laundry & Deck #201, holiday rental in Glengary

1200 SqFt Condo Above Abolitionist Ale Works Charles Town w/ Laundry & Deck #201

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private Downtown Charles Town Condo w/ Laundry Above Abolitionist Ale Works #202, holiday rental in Glengary

Private Downtown Charles Town Condo w/ Laundry Above Abolitionist Ale Works #202

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Couples Cabin - 5 Mi to DT Berkeley Springs!, holiday rental in Glengary

Couples Cabin - 5 Mi to DT Berkeley Springs!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Above Sleepy Hollow, holiday rental in Glengary

Above Sleepy Hollow

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Berkeley Springs Cottage - The Lane's End, holiday rental in Glengary

Berkeley Springs Cottage - The Lane's End

2 bedrooms
2 bathrooms
Sleeps 6
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Just Like Heaven Carriage House, holiday rental in Glengary

Just Like Heaven Carriage House

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Come see us near historic Harper's Ferry West Virginia, holiday rental in Glengary

Come see us near historic Harper's Ferry West Virginia

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Exquisite True Log Cabin/Chalet Rental, holiday rental in Glengary

Exquisite True Log Cabin/Chalet Rental

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sleepy Creek Retreat, holiday rental in Glengary

Sleepy Creek Retreat

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Country Time, holiday rental in Glengary

Country Time

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Wood Song, holiday rental in Glengary

Wood Song

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private One Bedroom Condo in Historic Downtown Charles Town Above Microbrewery, holiday rental in Glengary

Private One Bedroom Condo in Historic Downtown Charles Town Above Microbrewery

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Private Historic 2 Bedroom Condo in Heart of Downtown Charles Town #200, holiday rental in Glengary

Private Historic 2 Bedroom Condo in Heart of Downtown Charles Town #200

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Compound Historic Nature Preserve, holiday rental in Glengary

Compound Historic Nature Preserve

1 bedroom
1 bathroom
Sleeps 15
Match: Sleeps
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Creekside Berkeley Springs Cabin on 35 Acres!, holiday rental in Glengary

Creekside Berkeley Springs Cabin on 35 Acres!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Berkeley Springs Haven w/ Sleepy Creek Access, holiday rental in Glengary

NEW! Berkeley Springs Haven w/ Sleepy Creek Access

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Luxury Chalet ~ Private Yoga Studio/Gym ~ 30 miles to ski ~Hot Tub ~ Game Tables, holiday rental in Glengary

Luxury Chalet ~ Private Yoga Studio/Gym ~ 30 miles to ski ~Hot Tub ~ Game Tables

5 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Comfort at The Woods Resort, holiday rental in Glengary

Comfort at The Woods Resort

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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2 Bed Condo w Laundry Above Abolitionist Ale Works in Historic Charles Town #301, holiday rental in Glengary

2 Bed Condo w Laundry Above Abolitionist Ale Works in Historic Charles Town #301

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Large 2 Bedroom Condo Above Abolitionist Ale Works w/ Laundry & Balcony #201, holiday rental in Glengary

Large 2 Bedroom Condo Above Abolitionist Ale Works w/ Laundry & Balcony #201

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Historic 2 Bed Condo at Abolitionist Ale Works w/ Laundry & Balcony #300, holiday rental in Glengary

Historic 2 Bed Condo at Abolitionist Ale Works w/ Laundry & Balcony #300

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Chalet Cabin with Private Lake, WiFi, & Huge Deck!, holiday rental in Glengary

Chalet Cabin with Private Lake, WiFi, & Huge Deck!

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Loft Cabin w Huge Deck, Private Lake/Beach, WiFi!, holiday rental in Glengary

Loft Cabin w Huge Deck, Private Lake/Beach, WiFi!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Secluded Oasis w Hot Tub, Screened-in Porch, WiFi!, holiday rental in Glengary

Secluded Oasis w Hot Tub, Screened-in Porch, WiFi!

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cabin w Hot Tub, River/Kayak, WiFi, & Fire Pit!, holiday rental in Glengary

Cabin w Hot Tub, River/Kayak, WiFi, & Fire Pit!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Chalet Cabin w Huge Deck, Fire Pit, & Jacuzzi Tub!, holiday rental in Glengary

Chalet Cabin w Huge Deck, Fire Pit, & Jacuzzi Tub!

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Coolfont Cabin: Huge Deck, Grill, 10 Mins to Town!, holiday rental in Glengary

Coolfont Cabin: Huge Deck, Grill, 10 Mins to Town!

6 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Clean, Comfortable and Relaxing Short & Long Term Rentals, holiday rental in Glengary

Clean, Comfortable and Relaxing Short & Long Term Rentals

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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