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

Search Chalets in Winchester from CA $416

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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)
"If I could give more stars I would. What a beautiful home. Extremely clean and tastefully decorated. We enjoyed the turntable, hot tub, and extremely well equipped kitchen. A large fire pit, an outside dome to star gaze, comfortable deck out back with a grill, and plenty rockers on the front porch. My husband and I stayed 4 nights for our anniversary and were able to relax comfortably and spend some quality time together. We stopped by the grocery on the way and other than a few scenic rides,...
United States
Cynthia T.
The price is CA $354
CA $957 total
includes taxes & fees
Oct 25 - Oct 26
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.
The price is CA $229
CA $489 total
includes taxes & fees
Nov 3 - Nov 4
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.
The price is CA $374
CA $657 total
includes taxes & fees
Nov 2 - Nov 3
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.
The price is CA $276
CA $552 total
includes taxes & fees
Oct 26 - Oct 27
Mountain chalet w/ hot tub & private balcony
A spacious wooden deck with seating and a table, large windows offering a forest view.

5. Cozy Cottage w Enclosed Porch, Fireplace & Grill

Cozy Cottage w Enclosed Porch, Fireplace & Grill
The Woods
The price is CA $229
CA $585 total
includes taxes & fees
Oct 15 - Oct 16
Cozy Cottage w Enclosed Porch, Fireplace & Grill
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.
The price is CA $212
CA $416 total
includes taxes & fees
Nov 9 - Nov 10
Modern w Mountain Views, Hot Tub, Deck & Fire Pit
An outdoor patio area with a barbecue grill, seating, and large windows offering a view of the trees.

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

Berkeley Springs w/Hot Tub + Game Room + Fire Pit
Berkeley Springs
The price is CA $230
CA $483 total
includes taxes & fees
Nov 2 - Nov 3
Berkeley Springs w/Hot Tub + Game Room + Fire Pit
A wooden cabin with a metal roof, surrounded by snow and trees.

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

Pet-Friendly w Fire Pit, Grill & Resort Access
The Woods
The price is CA $229
CA $600 total
includes taxes & fees
Oct 15 - Oct 16
Pet-Friendly w Fire Pit, Grill & Resort Access
A log cabin with a stone chimney, a porch, and a small attached shed.

9. 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.
The price is CA $238
CA $521 total
includes taxes & fees
Nov 1 - Nov 2
Historic chalet w/ porch & BBQ grill
A balcony with a wooden deck, a grey sofa, and a built-in barbecue grill.

10. 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.
The price is CA $271
CA $557 total
includes taxes & fees
Nov 9 - Nov 10
Modern Escape w Mountain Views, Fire Pit & Swing
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.
The price is CA $229
CA $545 total
includes taxes & fees
Oct 20 - Oct 21
Cabin w Fire Pit, Hot Tub, Screened Porch & More
A single-story house with a balcony, a chimney, and a deck.

12. 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.
The price is CA $235
CA $590 total
includes taxes & fees
Nov 9 - Nov 10
Valley Views, Hot Tub, Deck, Screened Porch & WiFi
A wooden porch with a bench and a table, a 'HELLO' sign, and a 'WELCOME' sign.

13. 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.
The price is CA $333
CA $604 total
includes taxes & fees
Oct 26 - Oct 27
Cozy w/Fire Pit, Grill, 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)
The price is CA $227
CA $509 total
includes taxes & fees
Oct 15 - Oct 16
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.
The price is CA $303
CA $620 total
includes taxes & fees
Nov 3 - Nov 4
Forest chalet w/ hot tub & BBQ grill
A hot tub with a wooden deck and railing, surrounded by trees and a grassy area.

16. Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!

Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!
Harpers Ferry
9.2 out of 10, Wonderful, (23 reviews)
"Had a wonderful stay. House was perfect for our needs. Host was very responsive to any questions we had. Check-in was very easy. House was clean. "
United States
Van P.
The price is CA $423
CA $791 total
includes taxes & fees
Oct 20 - Oct 21
Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!
A hot tub on a wooden deck surrounded by a forest.

17. 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.
The price is CA $270
CA $545 total
includes taxes & fees
Oct 21 - Oct 22
Dog-Friendly Chalet w/Hot Tub, Fire Pit & Deck
Outdoor spa tub

18. 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.
The price is CA $194
CA $467 total
includes taxes & fees
Oct 20 - Oct 21
Mountain retreat chalet w/ hot tub & deck
A log cabin with a stone foundation, a porch, and a stone chimney.

19. 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)
"Beautiful house!!!! Great to get away but close enough to Cacapon Resort for all your interests. Then a few minutes your in Berkeley Springs with a whole different atmosphere. Great for couples, families or friends!!! If you get an opportunity to stop in at Cheers tell Debbie to “say less” lol. Great people and great place to call home for however long you are there!!"
United States
Anonymous traveller
The price is CA $254
CA $542 total
includes taxes & fees
Nov 9 - Nov 10
Mountain Retreat w Hot Tub, Grill, Deck & More!
A wooden deck with a table and chairs, large windows, and a view of trees.

20. 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.
The price is CA $228
CA $536 total
includes taxes & fees
Oct 15 - Oct 16
This chalet is a 3 bedroom(s), 2 bathrooms, located in Hedgesville, WV.
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 4 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

Find out more about Winchester

Winchester Chalets information

Number of reviews
163
Accommodation
66 Chalets
Lowest Price
CA $416
Highest Price
CA $957

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