Search Cottages in Winchester

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Cottages in Winchester

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (36)
"We enjoyed the stay and it was an easy walk to the places we wanted to go!"
The price is SAR 394
SAR 668 total
includes taxes & fees
9 Jun - 10 Jun
The Carriage House at Carrot Top Cottage

Cozy Retreat - Hot tub + Mountain Views + Pets

9.6 out of 10, Exceptional, (35)
"Great time at a great place"
The price is SAR 348
SAR 1,000 total
includes taxes & fees
15 Jun - 16 Jun
Cozy Retreat - Hot tub + Mountain Views + Pets

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

10.0 out of 10, Exceptional, (61)
"We had a long weekend visit to Luray and the central Shenandoah Valley and this was the perfect spot to stay. Beautiful, well maintained accommodations. We loved it."
The price is SAR 567
SAR 1,186 total
includes taxes & fees
12 Jun - 13 Jun
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (41)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is SAR 1,031
SAR 1,477 total
includes taxes & fees
6 Jul - 7 Jul
18th Century Stone Cottage minutes from historic Middleburg

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
10.0 out of 10, Exceptional, (13)
"We loved our stay. The location was central to everything we did; the car stayed in the driveway for almost our entire trip, and the yard is perfect for dogs. The house itself is exactly as shown in the pcs. Highly recommended "
The price is SAR 694
SAR 1,209 total
includes taxes & fees
15 Jun - 16 Jun
Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!

10.0 out of 10, Exceptional, (177)
"I loved my stay! The cottage was clean and cozy, and being able to use the hot tub was amazing. Ed and Betsy and all the animals were welcoming. The cottage was especially beautiful during sunrise. A very peaceful environment to stay in. "
Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!

Peaceful Lakefront Cottage with Mountain Views!

9.8 out of 10, Exceptional, (26)
"Wintertime visit. Very peaceful. "
Peaceful Lakefront Cottage with Mountain Views!

Firehouse Cottage | Walk to all of downtown HF

9.0 out of 10, Wonderful, (2)
"Walking is easy to downtown. Property is quiet location. Enjoyed our stay without ouo"
The price is SAR 544
SAR 906 total
includes taxes & fees
19 Jun - 20 Jun
Firehouse Cottage | Walk to all of downtown HF

Wild & Cozy | Harpers Ferry Mountain Escape

10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay, the four bedrooms gave us lots of space. The hot tub was great and we enjoyed the balcony, too. Very close to lots of fun wineries and Harper’s Ferry. Quiet location on a road with other houses. I’d recommend bringing extra towels and a few wine glasses if you’re drinking nice wine. Lots of thoughtful touches — games, fireplace, spacious kitchen. It was great!"
The price is SAR 424
SAR 1,486 total
includes taxes & fees
10 Jun - 11 Jun
Wild & Cozy | Harpers Ferry Mountain Escape

Cozy Stone Cottage in Round Hill, VA

10.0 out of 10, Exceptional, (3)
"We had an excellent stay at cottage! It was perfect for a short weekend away with girlfriends. It was quaint and historic but didn't lack modern day comforts. Highly recommend for anyone looking for a few days away, with easy access to all Round Hill & Purcellville has to offer. "
Cozy Stone Cottage in Round Hill, VA

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (120)
"The hosts are wonderful. I had a great time in their cozy, clean and beautiful place. Highly recommend for a visit to beautiful and historic WV.I particularly appreciated their fondness for dogs. Mine had a great time too!"
RIVERKEEPER INN, Waterfront Property on the Potomac River

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (41)
"Had a wonderful stay - - beautiful country and delightful cottage."
Historical cottage in the town of Paris

Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

9.8 out of 10, Exceptional, (26)
"We enjoyed our stay. Communications were great and the house was as described. No issues."
The price is SAR 1,333
SAR 2,707 total
includes taxes & fees
2 Jul - 3 Jul
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (35)
"This cottage was like a home away from home! It was the perfect location and spotless. We would definitely stay again and recommend to anyone "
Carrot Top Cottage surrounded by National Park

Brookside Cottage is a beautiful open concept doll house stay for two.

10.0 out of 10, Exceptional, (12)
"Close to town, great location, nice selection of restaurants but the town shuts down early. Bath house and Atasia spa both very nice. Recommend a visit for a day or one night visit."
Brookside Cottage is a beautiful open concept doll house stay for two.

Lake View Retreat - Cottage Near a Peaceful Lake!

9.6 out of 10, Exceptional, (17)
"Was really able to relax and enjoy during our brief stay. Would come again."
The price is SAR 375
SAR 1,348 total
includes taxes & fees
17 Jun - 18 Jun
Lake View Retreat - Cottage Near a Peaceful Lake!

Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.

9.4 out of 10, Exceptional, (9)
"What a stay. Beautiful property, excellent communication with the host, very nice accommodations. "
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.

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

10.0 out of 10, Exceptional, (17)
"We loved this place! It had everything we needed and everything was very comfortable. The sunset view from the hot tub was a highlight! We would stay here again."
The price is SAR 608
SAR 1,748 total
includes taxes & fees
15 Jun - 16 Jun
Cottage w/ Hot Tub and 100-Mile Valley Views!

Coolfont 4 BDRM, lots of beds! Cozy Wooded Cottage.

9.2 out of 10, Wonderful, (119)
"Perfect house and setting for a friend group. Lots of comfortable spaces and great setting!"
Coolfont 4 BDRM, lots of beds! Cozy Wooded Cottage.

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

10.0 out of 10, Exceptional, (18)
"Check in was seamless. The place was perfect for three couples with all the master suites. "
The price is SAR 593
SAR 1,943 total
includes taxes & fees
12 Jun - 13 Jun
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
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.
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Why book your cottage in Winchester with Expedia?
We think that vacations should be simple, so if you’re in search of cottages in Winchester at a competitive price, Expedia has got your back. Keep costs down and check in to a cheap option far away from the city rush, or splurge on an upmarket cottage to spoil your favorite people.
How can I find cheap cottages in Winchester?
The easiest way to locate cheap cottages in Winchester is with Expedia’s useful filter tool. Narrow your search results by star rating, amenities and budget to snag awesome prices in just a few keystrokes.