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Clear Brook Holiday Rentals

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Our top choices for Clear Brook holiday rentals

1. Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
8.8 out of 10, Excellent, (10 reviews)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
United States
Anonymous traveller
The price is NZ$298
includes taxes & fees
16 Aug - 17 Aug
Cozy English Basement Apt quiet but close to downtown

2. Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.6 out of 10, Exceptional, (9 reviews)
"This was yhe perfect place for us to stay in Old Winchester. A short walk to just about everything. The apartment was clean and comfortable. We had no issues with checking in and communication was great with the property owner. We would definitely rent from them again."
United States
Stephanie L.
The price is NZ$365
includes taxes & fees
30 Aug - 31 Aug
Pretty Little Apt by the Train II

3. Stone chalet w/ views & hot tub

Stone chalet w/ views & hot tub
Gerrardstown
9.0 out of 10, Wonderful, (43 reviews)
"Lovely, cozy cabin. Hot tub was very relaxing. Overall a wonderful place to stay."
United States
Michael H.
Stone chalet w/ views & hot tub

4. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.2 out of 10, Wonderful, (18 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
The price is NZ$565
includes taxes & fees
10 Sept - 11 Sept
Nostalgia Lane in the heart of the city

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

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
8.2 out of 10, Very good, (19 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
The price is NZ$594
includes taxes & fees
14 Sept - 15 Sept
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

6. 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 NZ$553
includes taxes & fees
16 Aug - 17 Aug
Forest 2BR chalet w/ hot tub & backyard

7. WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Old Town Winchester
9.0 out of 10, Wonderful, (10 reviews)
"Great location…"
United States
John P.
The price is NZ$667
includes taxes & fees
22 Aug - 23 Aug
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

8. 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 NZ$491
includes taxes & fees
24 Aug - 25 Aug
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly

9. Indigo Blue modern open vibe on tree lined street

Indigo Blue modern open vibe on tree lined street
Winchester Historic District
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! The place was very clean and exactly as described. Michele communicated clearly and responded quickly, which made everything easy from check-in to check-out. The location was also perfect—very close to downtown and convenient to everything we wanted to do. We would definitely stay here again and highly recommend it to others!"
United States
Elaina R.
The price is NZ$684
includes taxes & fees
16 Aug - 17 Aug
Indigo Blue modern open vibe on tree lined street

10. Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.8 out of 10, Exceptional, (7 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is NZ$667
includes taxes & fees
23 Aug - 24 Aug
Scarborough Fair walk to downtown two story apt

11. Peaceful mountain cabin in charming Berryville VA - next to river and brewery

Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Berryville
10.0 out of 10, Exceptional, (1 review)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveller
The price is NZ$410
includes taxes & fees
21 Aug - 22 Aug
Peaceful mountain cabin in charming Berryville VA - next to river and brewery

12. Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.

Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.
Cross Junction
9.6 out of 10, Exceptional, (86 reviews)
"The best, peaceful, fun, ATV wheeling, target practice, grilling, great kitchen supplies and plenty of space for the family Would stay again"
United States
Lisa G.
The price is NZ$528
includes taxes & fees
19 Aug - 20 Aug
Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (82 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is NZ$239
includes taxes & fees
31 Aug - 1 Sept
❤️ Secluded 1940s Romantic Tiny House on the River

14. Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (26 reviews)
"We enjoyed our stay and the property was exactly what we were looking for in a mountain getaway peaceful, private, and immersed in the woods with beautiful views and a relaxing atmosphere.The home was clean, quiet, and met our needs well for a restful escape. The hosts were communicative and supportive, although we did not need to reach out during our stay.The driveway is definitely mountain-style, so guests should come prepared and be mindful of the vehicle they bring, but the secluded setting...
United States
B S.
The price is NZ$647
includes taxes & fees
31 Aug - 1 Sept
Cottage w/ Hot Tub and 100-Mile Valley Views!

15. Cabin at the Gap | You Won't Believe the View!

Cabin at the Gap | You Won't Believe the View!
Harpers Ferry
The price is NZ$567
includes taxes & fees
16 Aug - 17 Aug
Cabin at the Gap | You Won't Believe the View!

16. Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (11 reviews)
"The house was wonderfully situated and stocked for our needs. It is very well kept and decorated. We enjoyed our stay very much!"
United States
Shawn P.
The price is NZ$312
includes taxes & fees
24 Aug - 25 Aug
Luxury tiny home farm stay on historic property with hot tub in Stephens City

17. 4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Harpers Ferry
9.6 out of 10, Exceptional, (9 reviews)
"House was beautiful and fully equipped for our stay. The host was very communicative and we really enjoyed our time here. If in the area again would definitely stay here. "
United States
Maeve K.
The price is NZ$757
includes taxes & fees
1 Sept - 2 Sept
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

18. Blue Ridge Getaway - Sunset Views, A.T. Access

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (75 reviews)
"This was an absolutely amazing stay. Beautiful location, extremely comfortable. Well stocked kitchen. Wonderful hot tub. Perfection for a getaway."
United States
Andrew L.
The price is NZ$609
includes taxes & fees
19 Aug - 20 Aug
Blue Ridge Getaway - Sunset Views, A.T. Access

19. Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!
Harpers Ferry
9.8 out of 10, Exceptional, (26 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
Woodsy Retreat with a Hot Tub and Seasonal Views!

20. Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (19 reviews)
"We had a wonderful stay. The communication and the guestbook were wonderful. The view was gorgeous and the property was clean and comfortable. "
United States
Kaitlyn C.
The price is NZ$665
includes taxes & fees
24 Aug - 25 Aug
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
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 Clear Brook Hotel Reviews

Find out more about Clear Brook

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Clear Brook holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Clear Brook. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Clear Brook. Seeing all the best attractions is bound to make you fall in love with Clear Brook. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Clear Brook short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Clear Brook?

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

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.: This holiday home rental outside of Clear Brook offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Clear Brook?

Clearbrook Park and Clearbrook Lake are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Clearbrook Park Playground and Mackintosh Fruit Farm.

What’s a holiday rental in Clear Brook like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Clear Brook. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for family trips.