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Check prices for these dates

Next weekend
14 Rab. I - 16 Rab. I
In two weeks
21 Rab. I - 23 Rab. I
In one month
4 Rab. II - 6 Rab. II
In two months
2 Jum. I - 4 Jum. I

Compare 148 Cottages in Winchester with updated reviews, rates, and availability.

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, (49)
"This home is just lovely and is in a great location. Neighbors are friendly and I had to call AAA for a flat tire and the local tow truck driver was an earth angel. Can't wait to stay here again!"
The price is SAR 600
SAR 1,228 total
includes taxes & fees
9 Mar - 10 Mar
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Carrot Top Cottage surrounded by National Park
Exterior

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (34)
"Very well stocked, clean, great communication from host, convenient, would definitely recommend "
Carrot Top Cottage surrounded by National Park
Cozy Retreat - Hot tub + Mountain Views + Pets
Smart TV, stereo

Cozy Retreat - Hot tub + Mountain Views + Pets

10.0 out of 10, Exceptional, (24)
"Lovely spot. Definitely Recommend it! "
The price is SAR 290
SAR 953 total
includes taxes & fees
4 Mar - 5 Mar
Cozy Retreat - Hot tub + Mountain Views + Pets
Secluded, Cozy Cottage in the Shenandoah Valley

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (167)
"We had an absolutely amazing stay at this charming cabin! Nestled in the serene mountains, it’s the perfect place to unwind and recharge. The cabin was cozy and inviting, with a beautiful fireplace that made the evenings so warm and relaxing. We loved soaking in the jacuzzi after a day of exploring the area—it was the perfect touch!The host was incredibly responsive and went above and beyond to ensure our stay was comfortable. We were especially delighted by the homemade cookies that greeted us...
Secluded, Cozy Cottage in the Shenandoah Valley
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (37)
"The cottage is perfect for a couple. Small, cozy, plenty of room. The heating system takes some learning, but the fireplace is easy. The grounds are beautiful and if the weather cooperates, take the time to walk around them.Proximity to Middleburg and Upperville makes it even better.I hope to return."
The price is SAR 1,031
SAR 1,469 total
includes taxes & fees
18 Mar - 19 Mar
18th Century Stone Cottage minutes from historic Middleburg
Bear Chase Cottage
Property grounds

Bear Chase Cottage

10.0 out of 10, Exceptional, (33)
"The staff and property were wonderful. Everyone was so helpful; it was nice to be able to walk up to the restaurant and see the amazing mountain views with fire pits and lookouts. It was an added surprise to see the home decorated for the holidays! "
Bear Chase Cottage
Beautiful 360 views!
Exterior

Beautiful 360 views!

10.0 out of 10, Exceptional, (173)
"We had a wonderful time staying here. Every morning was amazing with the sun rises, the space was cozy and comfy. We fully enjoyed ourselves."
Beautiful 360 views!
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Interior

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

10.0 out of 10, Exceptional, (1)
"We had a a great experience at this cabin getaway. The property was immaculate, cozy and well-equipped. The host was incredibly responsive and thoughtful. We can't wait to come back!"
The price is SAR 938
SAR 1,591 total
includes taxes & fees
5 Mar - 6 Mar
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond
Exterior

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond
The Carriage House at Carrot Top Cottage
Aerial view

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (33)
"This small little cottage was just the right size for our stay. The location was perfect being beside the Appalachian trail and waking up to deer every morning. "
The price is SAR 368
SAR 639 total
includes taxes & fees
6 Mar - 7 Mar
The Carriage House at Carrot Top Cottage
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)
"What a lovely, cozy, clean property! The location was in the heart of Harper’s Ferry. Everything advertised was exactly as described, even nicer, inside and out! Cathy, our property manager was communicative and helpful. We will be back!!"
The price is SAR 619
SAR 1,117 total
includes taxes & fees
4 Mar - 5 Mar
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Royal Heritage Home @ Historic Leesburg
Fridge, microwave, oven, stovetop

Royal Heritage Home @ Historic Leesburg

9.8 out of 10, Exceptional, (24)
"We stayed at this property during our annual visit to Leesburg. We enjoy the downtown area (easy to walk) and catching an Uber to the local vineyards! House was perfect for our group of 5. Majority of our time at the house was spent sleeping, but we all felt comfortable and had enough space. Three bathrooms were great! "
The price is SAR 791
SAR 1,743 total
includes taxes & fees
4 Mar - 5 Mar
Royal Heritage Home @ Historic Leesburg
Lovettsville Cottage in Heart of Wine Country
TV, Netflix, streaming services

Lovettsville Cottage in Heart of Wine Country

9.8 out of 10, Exceptional, (32)
"Perfect for the weekend getaway we were looking for! Beautiful guest home that was very clean and was well stocked with anything we might need. Only one issue was there were lots of stink bugs in the house but I imagine in the winter that would be more of a problem then in the warmer months. "
Lovettsville Cottage in Heart of Wine Country
COZY CABIN. One room cabin with loft.
Outdoor dining

COZY CABIN. One room cabin with loft.

10.0 out of 10, Exceptional, (3)
"My friend and I came up to do some biking on the C&O and western Maryland rail trail, and to also do some hiking! Weather was perfect and the cozy cabin fit all our needs perfectly!. Very cutely decorated…Clean…Beautiful views. The host even invited us for dinner one night if we wanted to join them! Check in was easy and there was even a few snacks and waters provided. All very thoughtful gestures. We were warned that there was a two mile stretch of rougher road leading up to the cabin but...
COZY CABIN. One room cabin with loft.
Spectacular Cottage with Shenandoah River Views
Fridge, microwave, oven, stovetop

Spectacular Cottage with Shenandoah River Views

10.0 out of 10, Exceptional, (206)
"Overall this was a great place for a getaway with my husband! The cottage is very well done. It's incredibly clean, well stocked, and the furnishings and supplies are quite nice. The view is absolutely gorgeous and very peaceful. The "downsides" were that a bridge is under construction until late 2025 in the area so it takes longer to get to any stores. The last 5 minutes to the property are complete gravel roads and the very last part is a little steep. It's secluded but there is a house next...
Spectacular Cottage with Shenandoah River Views
Riversong Luxe Cabin w/ Fire Pit on North River
House (3 Bedrooms) | Interior

Riversong Luxe Cabin w/ Fire Pit on North River

3.0 star property
Riversong Luxe Cabin w/ Fire Pit on North River
RIVERKEEPER INN, Waterfront Property on the Potomac River
View from property

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (116)
"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
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (38)
"What a lovely and comfortable cottage! "
Historical cottage in the town of Paris
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Outdoor dining

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 SAR 581
SAR 1,917 total
includes taxes & fees
10 Mar - 11 Mar
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
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)
"Beautiful location to relax and enjoy friends. This house was huge. Plenty of room for the 3 of us...could have been 8, lol. "
The price is SAR 375
SAR 1,316 total
includes taxes & fees
6 Mar - 7 Mar
Lake View Retreat - Cottage Near a Peaceful Lake!
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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Other property types in Winchester

Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Outdoor dining

Charming mountaintop cabin with hot tub, pool table, and breathtaking views

9.8 out of 10, Exceptional, (196)
"We booked the cabin for a weekend get away. The cabin was great. My boyfriend purposed to me and I left the ring at the cabin! Please contact me ASAP! "
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (304)
"We experienced the beauty of a mountain snowstorm and it was awesome! We enjoyed the gorgeous view sitting by the fireplace and feeling super cozy. Nina the owner was so thoughtful, checking on us, suggesting a good place for our car during the storm so that we wouldn’t get stuck when it came time to go home, even cleaning our car off for us! That was above and beyond—thank you, Nina. The cabin is as pictured and well appointed. We plan to return here. "
Star view cabin-Riverfront
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
2 bedrooms, WiFi, bed sheets

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

9.6 out of 10, Exceptional, (342)
"We were looking for a weekend getaway to do some hiking in Shenendoah and the Cozy Cabin was perfect! The views from the deck were gorgeous, and loved having a fireplace in the living room and bedroom on a cold weekend. Close to Front Royal, and the park - overall very happy with our stay!"
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
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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