A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Winchester Chalets

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winchester chalets

A cozy outdoor seating area with wicker chairs and a wooden deck.

1. Secluded Luxury Cabin with Stargazing Dome + Hot Tub + Sauna + EV Charger

Secluded Luxury Cabin with Stargazing Dome + Hot Tub + Sauna + EV Charger
Harpers Ferry
10.0 out of 10, Exceptional, (2 reviews)
"Super nice place. We enjoyed everything about it, and it rained the entire time. Everything seems brand new (dishes, fireplace, furniture). Would love to come back and stay again."
United States
Geoff D.
$603 nightly
The price is $670
Oct 25 - Oct 26
Total with taxes and fees
Secluded Luxury Cabin with Stargazing Dome + Hot Tub + Sauna + EV Charger
Forest Haven is beautiful at night

2. 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.
$305 nightly
The price is $340
Oct 22 - Oct 23
Total with taxes and fees
Forest 2BR chalet w/ hot tub & backyard
A wooden deck with a hot tub, outdoor seating, and a view of a forested area.

3. 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.
$381 nightly
The price is $413
Nov 2 - Nov 3
Total with taxes and fees
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
Exterior

4. Mountain chalet w/ hot tub & private balcony

Mountain chalet w/ hot tub & private balcony
Augusta
9.6 out of 10, Exceptional, (15 reviews)
"Tony is a wonderful and communicative host! We had a great, relaxing weekend here. "
United States
Leigh Ann P.
$352 nightly
The price is $381
Oct 26 - Oct 27
Total with taxes and fees
Mountain chalet w/ hot tub & private balcony
A wooden cabin with a metal roof, surrounded by snow and trees.

5. Pet-Friendly w Fire Pit, Grill & Resort Access

Pet-Friendly w Fire Pit, Grill & Resort Access
The Woods
$384 nightly
The price is $417
Oct 15 - Oct 16
Total with taxes and fees
Pet-Friendly w Fire Pit, Grill & Resort Access
A hot tub on a wooden deck with a red umbrella, surrounded by greenery and a clear sky.

6. 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, (15 reviews)
"Beautiful get away"
United States
Brett R.
$269 nightly
The price is $290
Nov 3 - Nov 4
Total with taxes and fees
Modern w Mountain Views, Hot Tub, Deck & Fire Pit
A log cabin with a stone chimney, a porch, and a small attached shed.

7. Historic chalet w/ porch & BBQ grill

Historic chalet w/ porch & BBQ grill
Capon Bridge
10.0 out of 10, Exceptional, (1 review)
"Comfortable, sheets were outstanding! Host was very accommodating and answered questions right away. Could use a little more lighting, stairs were dark. "
United States
Linda C.
$334 nightly
The price is $361
Nov 1 - Nov 2
Total with taxes and fees
Historic chalet w/ porch & BBQ grill
A spacious wooden deck with seating and a table, large windows offering a forest view.

8. Cozy Cottage w Enclosed Porch, Fireplace & Grill

Cozy Cottage w Enclosed Porch, Fireplace & Grill
The Woods
$379 nightly
The price is $412
Oct 15 - Oct 16
Total with taxes and fees
Cozy Cottage w Enclosed Porch, Fireplace & Grill
A balcony with a wooden deck, a grey sofa, and a built-in barbecue grill.

9. Modern Escape w Mountain Views, Fire Pit & Swing

Modern Escape w Mountain Views, Fire Pit & Swing
Martinsburg
9.0 out of 10, Wonderful, (2 reviews)
"Buestiful location and property. House was exactly as described and wonderful. My family and I truly enjoyed our time here."
United States
Kevin S.
$363 nightly
The price is $394
Nov 9 - Nov 10
Total with taxes and fees
Modern Escape w Mountain Views, Fire Pit & Swing
An outdoor patio area with a barbecue grill, seating, and large windows offering a view of the trees.

10. Berkeley Springs w/Hot Tub + Game Room + Fire Pit

Berkeley Springs w/Hot Tub + Game Room + Fire Pit
Berkeley Springs
$312 nightly
The price is $337
Nov 2 - Nov 3
Total with taxes and fees
Berkeley Springs w/Hot Tub + Game Room + Fire Pit
A single-story house with a large front porch, a covered deck, and a chimney.

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

Cabin w Fire Pit, Hot Tub, Screened Porch & More
The Woods
9.8 out of 10, Exceptional, (6 reviews)
"Great little place for a mini trip away. Host was really helpful and great when I had questions. The house was adorable and was perfect for us. Hot tub on the deck was wonderful. Lots of little extra items in case you forgot things so that was a huge plus. Highly recommend!"
United States
Katlin M.
$350 nightly
The price is $379
Oct 15 - Oct 16
Total with taxes and fees
Cabin w Fire Pit, Hot Tub, Screened Porch & More
A wooden porch with a bench and a table, a 'HELLO' sign, and a 'WELCOME' sign.

12. Cozy w/Fire Pit, Grill, Screened Porch & WiFi

Cozy w/Fire Pit, Grill, Screened Porch & WiFi
Harpers Ferry
9.8 out of 10, Exceptional, (7 reviews)
"The host was very communicative and the place was very clean. "
United States
Christopher M.
$390 nightly
The price is $423
Oct 26 - Oct 27
Total with taxes and fees
Cozy w/Fire Pit, Grill, Screened Porch & WiFi
A single-story house with a balcony, a chimney, and a deck.

13. Valley Views, Hot Tub, Deck, Screened Porch & WiFi

Valley Views, Hot Tub, Deck, Screened Porch & WiFi
Sleepy Hollow
10.0 out of 10, Exceptional, (2 reviews)
"We had a great time, the views were amazing. The house was clean and comfortable. Everything you need it there. Tony was quick to respond with an questions we had. "
United States
Will S.
$378 nightly
The price is $410
Nov 9 - Nov 10
Total with taxes and fees
Valley Views, Hot Tub, Deck, Screened Porch & WiFi
A stone cabin with a wooden deck and a covered porch.

14. Rustic retreat w/ kitchen & deck

Rustic retreat w/ kitchen & deck
Great Cacapon
10.0 out of 10, Exceptional, (5 reviews)
"Loved the place and the secluded mountain setting. "
United States
melissa w.
$326 nightly
The price is $352
Oct 15 - Oct 16
Total with taxes and fees
Rustic retreat w/ kitchen & deck
A hot tub on a wooden deck with a white railing, surrounded by trees.

15. Forest chalet w/ hot tub & BBQ grill

Forest chalet w/ hot tub & BBQ grill
Harpers Ferry
9.2 out of 10, Wonderful, (35 reviews)
"Very nice cabin. Close to Harpers Ferry. Comfortable"
United States
Dianne A.
$403 nightly
The price is $437
Nov 4 - Nov 5
Total with taxes and fees
Forest chalet w/ hot tub & BBQ grill
A wooden deck with a table and chairs, large windows, and a view of trees.

16. This chalet is a 3 bedroom(s), 2 bathrooms, located in Hedgesville, WV.

This chalet is a 3 bedroom(s), 2 bathrooms, located in Hedgesville, WV.
The Woods
9.8 out of 10, Exceptional, (22 reviews)
"House was great and cozy for the family for a weekend away. Would stay here again."
United States
Brooke R.
$350 nightly
The price is $372
Oct 15 - Oct 16
Total with taxes and fees
This chalet is a 3 bedroom(s), 2 bathrooms, located in Hedgesville, WV.
Outdoor spa tub

17. Mountain retreat chalet w/ hot tub & deck

Mountain retreat chalet w/ hot tub & deck
Rio
9.6 out of 10, Exceptional, (7 reviews)
"Enjoyed our stay very much!! Enjoyed the hot tub and the space very much. "
United States
Melissa M.
$299 nightly
The price is $323
Oct 20 - Oct 21
Total with taxes and fees
Mountain retreat chalet w/ hot tub & deck
A hot tub on a wooden deck surrounded by a forest.

18. Dog-Friendly Chalet w/Hot Tub, Fire Pit & Deck

Dog-Friendly Chalet w/Hot Tub, Fire Pit & Deck
Berkeley Springs
9.6 out of 10, Exceptional, (4 reviews)
"Wonderful place, peaceful and quiet. Very clean!! Didn't have to travel to far if we wanted to find things to do.."
United States
Carrie S.
$343 nightly
The price is $371
Oct 20 - Oct 21
Total with taxes and fees
Dog-Friendly Chalet w/Hot Tub, Fire Pit & Deck
Terrace/patio

19. Chalet w Hot tub, Grill, FirePit, Games & Wifi

Chalet w Hot tub, Grill, FirePit, Games & Wifi
The Woods
9.0 out of 10, Wonderful, (2 reviews)
"This cabin exceeded our expectations! The host was outstanding, always friendly, attentive, and quick to respond. The cabin was extremely clean, cozy, and thoughtfully equipped with everything we needed. It felt like a home away from home. The peaceful atmosphere made it the perfect place to relax and spend quality time with family. We couldn’t have asked for a better experience and would absolutely stay here again. Highly recommended!"
United States
Lariana P.
$305 nightly
The price is $329
Nov 3 - Nov 4
Total with taxes and fees
Chalet w Hot tub, Grill, FirePit, Games & Wifi
A log cabin with a stone foundation, a porch, and a stone chimney.

20. Mountain Retreat w Hot Tub, Grill, Deck & More!

Mountain Retreat w Hot Tub, Grill, Deck & More!
Berkeley Springs
10.0 out of 10, Exceptional, (6 reviews)
"As advertised. We enjoyed our stay"
United States
Reed P.
$347 nightly
The price is $376
Nov 9 - Nov 10
Total with taxes and fees
Mountain Retreat w Hot Tub, Grill, Deck & More!
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 Winchester Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Friendly, professional staff. Most helpful with an issue I had with my car. Could not have been nicer and understanding."
DOUGLAS 2-night trip
Posted 11 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

Find out more about Winchester

Winchester Chalets information

Number of reviews
142
Accommodation
67 Chalets
Lowest Price
$290
Highest Price
$670

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