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
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 184 Cottages in Winchester with updated reviews, rates, and availability.

Secluded, Cozy Cottage in the Shenandoah Valley

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (170)
"We enjoyed our stay at this lovely property."
Secluded, Cozy Cottage in the Shenandoah Valley
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Bar (on property)

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

9.8 out of 10, Exceptional, (26)
"Our hosts were so wonderful!! The cottage is so cute and has everything one could need. We will definitely be repeat guests and recommend this place HIGHLY!!!"
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Smart TV, books

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

9.8 out of 10, Exceptional, (55)
"I loved this property! The inside was so cute and clean, and the property managers were very responsive to any questions we had. "
The price is AED 588
AED 1,194 total
includes taxes & fees
27 Apr - 28 Apr
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Cozy Retreat - Hot tub + Mountain Views + Pets
Smart TV, stereo

Cozy Retreat - Hot tub + Mountain Views + Pets

10.0 out of 10, Exceptional, (25)
"Great time at a great place"
The price is AED 322
AED 966 total
includes taxes & fees
29 Apr - 30 Apr
Cozy Retreat - Hot tub + Mountain Views + Pets
The Carriage House at Carrot Top Cottage
Aerial view

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (35)
"We enjoyed the stay and it was an easy walk to the places we wanted to go!"
The price is AED 386
AED 655 total
includes taxes & fees
27 Apr - 28 Apr
The Carriage House at Carrot Top Cottage
Carrot Top Cottage surrounded by National Park
Exterior

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
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Fridge, microwave, oven, stovetop

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

10.0 out of 10, Exceptional, (1)
"This was a good place to stay for two guys day hiking in the AT. It is clean, quiet, comfortable, and in a very good location. It had everything we needed."
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (39)
"We absolutely loved this little cottage. It's a great location near Middleburg, tucked back in the woods. It's got everything you need for a peaceful retreat. A perfect place to curl up in front of the fire with a book. The host was so welcoming and easy to work with. We'll definitely be back!"
The price is AED 1,010
AED 1,446 total
includes taxes & fees
27 Apr - 28 Apr
18th Century Stone Cottage minutes from historic Middleburg
Historical cottage in the town of Paris
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (40)
"Had a wonderful stay - - beautiful country and delightful cottage."
Historical cottage in the town of Paris
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Terrace/patio

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

9.4 out of 10, Exceptional, (8)
"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.
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Property grounds

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

10.0 out of 10, Exceptional, (16)
"Check in was seamless. The place was perfect for three couples with all the master suites. "
The price is AED 599
AED 1,917 total
includes taxes & fees
8 May - 9 May
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Dining

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

9.6 out of 10, Exceptional, (10)
"Excellent place to stay. Shelly is an excellent host. Nice location "
The price is AED 1,313
AED 1,850 total
includes taxes & fees
7 May - 8 May
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Cottage w/ Hot Tub and 100-Mile Valley Views!
Outdoor spa tub

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

10.0 out of 10, Exceptional, (15)
"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 AED 367
AED 1,390 total
includes taxes & fees
30 Apr - 1 May
Cottage w/ Hot Tub and 100-Mile Valley Views!
Royal Heritage Home @ Historic Leesburg
Fridge, microwave, oven, stovetop

Royal Heritage Home @ Historic Leesburg

9.6 out of 10, Exceptional, (27)
"Great location"
The price is AED 775
AED 1,744 total
includes taxes & fees
28 Apr - 29 Apr
Royal Heritage Home @ Historic Leesburg
Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns
Property grounds

Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns

9.6 out of 10, Exceptional, (207)
"Always a wonderful experience! A perfect retreat to relax and unwind. Hosts are always so gracious and accommodating. Will be back again!"
Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns
4 BDRM, lots of beds! Cozy Wooded Cottage.
Outdoor pool

4 BDRM, lots of beds! Cozy Wooded Cottage.

9.2 out of 10, Wonderful, (118)
"Perfect house and setting for a friend group. Lots of comfortable spaces and great setting!"
4 BDRM, lots of beds! Cozy Wooded Cottage.
Beautiful 360 views!
Exterior

Beautiful 360 views!

10.0 out of 10, Exceptional, (174)
"This is our third stay at this cottage. We wouldn't stay anywhere else."
Beautiful 360 views!
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Exterior detail

Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

9.8 out of 10, Exceptional, (7)
"This is our 5th stay at this beautiful cottage. We have recommended it to friends as well. The hosts have done everything to insure that your stay will be a wonderful experience. The cottage is immaculate and has everything you need to have a relaxing stay. I highly recommend it! "
The price is AED 650
AED 1,550 total
includes taxes & fees
28 Apr - 29 Apr
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Lake View Retreat - Cottage Near a Peaceful Lake!
Property grounds

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 AED 367
AED 1,309 total
includes taxes & fees
1 May - 2 May
Lake View Retreat - Cottage Near a Peaceful Lake!
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (9)
"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 AED 680
AED 1,199 total
includes taxes & fees
27 Apr - 28 Apr
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (312)
"very cute little place, would definitely stay again"
Star view cabin-Riverfront
Dreamtime - Modern A-frame Cabin w/ Hot tub
Outdoor dining

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (37)
"Great cabin. Clean and so welcoming"
The price is AED 1,062
AED 1,345 total
includes taxes & fees
7 May - 8 May
Dreamtime - Modern A-frame Cabin w/ Hot tub
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Miscellaneous

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (96)
"This was a perfect clean comfortable place to stay while exploring the Harper's Ferry area. Hosts Scott and Margie are friendly and welcoming"
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
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.