Shawnee Land Vacation Rentals

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Check prices for these dates

Tonight
Dec 16 - Dec 17
Tomorrow
Dec 17 - Dec 18
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for Shawnee Land vacation rentals

Terrace/patio
Large Glamper w/ Hot Tub and full bathroom-sleep 6

Mobile Home in Capon Bridge

Large Glamper w/ Hot Tub and full bathroom-sleep 6
9.8 out of 10, Exceptional, (24)
"We absolutely loved this place! The glamper had everything we needed and more! The hot tub was super relaxing and the host is super responsive! Would definitely stay here again in the future."
United States
Anonymous traveler
The price is ￥9,928
￥28,382 total
includes taxes & fees
Dec 17 - Dec 18
Large Glamper w/ Hot Tub and full bathroom-sleep 6
Interior
Very charming & spacious 2 bedrm

Apartment in Winchester

Very charming & spacious 2 bedrm
The price is ￥9,487
￥22,127 total
includes taxes & fees
Dec 21 - Dec 22
Very charming & spacious 2 bedrm
Smart TV, foosball
3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!

Vacation Home in Stephens City

3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!
9.2 out of 10, Wonderful, (7)
"Our stay here was outstanding. The house was clean, spacious, and close to many shops/restaurants. Our first evening we spent in downtown Winchester which was an easy drive from the home. The next day was spent at the Virginia Scottish Games, about 35 minutes away. The house was definitely worth the stay! We had a great time. It was even one of the best smelling houses we had ever rented! 100% recommend and would stay again. "
United States
Ashley B.
3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!
Fridge, microwave, oven, stovetop
Cozy w Hot Tub, Fire Pit, Wifi, Grill, Deck & Pets

Chalet in Rio

Cozy w Hot Tub, Fire Pit, Wifi, Grill, Deck & Pets
9.0 out of 10, Wonderful, (4)
"Clean, comfortable cabin, and very effective communication from the host."
United States
Keely
The price is ￥26,243
￥44,695 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Cozy w Hot Tub, Fire Pit, Wifi, Grill, Deck & Pets
Fridge, microwave, oven, stovetop
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Apartment in Winchester Historic District

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
2.0 star property
8.6 out of 10, Excellent, (4)
"Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best."
United States
matthew r.
The price is ￥21,391
￥36,706 total
includes taxes & fees
Dec 29 - Dec 30
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
TV, fireplace, offices
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

Cabin in Gerrardstown

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
8.2 out of 10, Very Good, (11)
"Our team had a fantastic stay at the chalet cabin rental. The hot tub, BBQ grille, and fire pit were all great amenities, and the wifi was a nice bonus. The huge primary suite upstairs and reading loft provided enough space for everyone to have their own space. We would highly recommend this chalet for work retreats or any group getaway"
United States
Manuel T.
The price is ￥22,662
￥40,724 total
includes taxes & fees
Dec 21 - Dec 22
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Fridge, microwave, oven, stovetop
Modern w Mountain Views, Hot Tub, Deck & Fire Pit

Chalet in Berkeley Springs

Modern w Mountain Views, Hot Tub, Deck & Fire Pit
9.6 out of 10, Exceptional, (9)
"Loved the hot tub and fire pit. Dogs enjoyed the secluded property."
United States
Sean R.
The price is ￥23,856
￥39,983 total
includes taxes & fees
Dec 18 - Dec 19
Modern w Mountain Views, Hot Tub, Deck & Fire Pit
Fridge, microwave, oven, stovetop
The Little Red Schoolhouse

Apartment in Cross Junction

The Little Red Schoolhouse
9.8 out of 10, Exceptional, (13)
"We loved the overall school house theme. Very comfortable accommodations! "
United States
Tony Z.
The price is ￥15,067
￥33,426 total
includes taxes & fees
Jan 14 - Jan 15, 2026
The Little Red Schoolhouse
Fridge, microwave, oven, stovetop
Upscale w Fireplace, Fire Pit, Games in Gated Comm

Cabin in Paw Paw

Upscale w Fireplace, Fire Pit, Games in Gated Comm
2.0 star property
9.6 out of 10, Exceptional, (5)
"The cabin was so detailed it blew me away amazing place to stay very relaxing and very secluded "
United States
Frank
The price is ￥28,289
￥55,224 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Upscale w Fireplace, Fire Pit, Games in Gated Comm
Fridge, microwave, oven, stovetop
River Access Cabin with Hot Tub, Fire Pit & WiFi!

Cabin in Berkeley Springs

River Access Cabin with Hot Tub, Fire Pit & WiFi!
9.2 out of 10, Wonderful, (27)
"THE CABIN WAS CLEAN AND WELL STOCKED, PERFECTLY AS DESCRIBED. LOVED THE HOT TUB! LOCATION WAS GREAT FOR WHAT WE INTENDED THE WEEKEND TO BE, RELAXING BUT CLOSE ENOUGH TO THE ENTERTAINMENT AS NEEDED."
United States
Jess R.
The price is ￥22,833
￥42,485 total
includes taxes & fees
Dec 17 - Dec 18
River Access Cabin with Hot Tub, Fire Pit & WiFi!
Outdoor dining
Newly renovated Farm cottage with Mountain views

Vacation Home in Strasburg

Newly renovated Farm cottage with Mountain views
10.0 out of 10, Exceptional, (38)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is ￥24,802
￥50,097 total
includes taxes & fees
Dec 21 - Dec 22
Newly renovated Farm cottage with Mountain views
Fridge, microwave, oven, stovetop
The Stock Exchange downtown 3rd floor studio apt

Apartment in Winchester Historic District

The Stock Exchange downtown 3rd floor studio apt
2.0 star property
6.0 out of 10, (1)
The Stock Exchange downtown 3rd floor studio apt
Interior
Rosamond nice downtown studio apt

Apartment in Winchester Historic District

Rosamond nice downtown studio apt
8.0 out of 10, Very Good, (2)
"Small but appropriately priced."
United States
John M.
Rosamond nice downtown studio apt
Interior
Pretty Little Apt by the Train II

Apartment in Old Town Winchester

Pretty Little Apt by the Train II
2.0 star property
9.8 out of 10, Exceptional, (7)
"Great time. Love this city"
United States
Barbara B.
The price is ￥20,255
￥33,541 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Pretty Little Apt by the Train II
Fridge, microwave, oven, stovetop
Yellow Submarine trendy basement apt and courtyard

Apartment in Old Town Winchester

Yellow Submarine trendy basement apt and courtyard
7.6 out of 10, Good, (4)
"We loved the character and personality kf both Winchester and"
United States
Jenna N.
The price is ￥22,631
￥38,812 total
includes taxes & fees
Dec 17 - Dec 18
Yellow Submarine trendy basement apt and courtyard
Terrace/patio
Hart's Overlook | HOT TUB, Mtn Views + Private Pond!

Cabin in Augusta

Hart's Overlook | HOT TUB, Mtn Views + Private Pond!
10.0 out of 10, Exceptional, (14)
"We had a very joyful stay at the property. The location, home, scenery and hot tube were perfect for our weekend. "
United States
Michelle D.
The price is ￥26,994
￥58,324 total
includes taxes & fees
Dec 17 - Dec 18
Hart's Overlook | HOT TUB, Mtn Views + Private Pond!
Terrace/patio
Cozy Cabin in Nature by National Park, EV Charger

Vacation Home in Star Tannery

Cozy Cabin in Nature by National Park, EV Charger
2.0 star property
10.0 out of 10, Exceptional, (5)
"This home was very secluded and had beautiful views. The interior was a perfect mix of historic and modern touches. Hosts were very responsive and we would stay here again!"
United States
Cyndi B.
The price is ￥27,906
￥56,044 total
includes taxes & fees
Dec 17 - Dec 18
Cozy Cabin in Nature by National Park, EV Charger
3 bedrooms, iron/ironing board, WiFi, bed sheets
Nostalgia Lane in the heart of the city

Apartment in Old Town Winchester

Nostalgia Lane in the heart of the city
9.0 out of 10, Wonderful, (14)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is ￥28,825
￥51,900 total
includes taxes & fees
Dec 17 - Dec 18
Nostalgia Lane in the heart of the city
Outdoor spa tub
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly

Chalet in Gerrardstown

Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
9.4 out of 10, Exceptional, (11)
"We had a fabulous time and highly recommend this rental."
United States
Amber H.
The price is ￥28,949
￥48,273 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
Outdoor spa tub
Sun Valley Overlook A-Frame | Wow Views + Hot Tub

Vacation Home in Augusta

Sun Valley Overlook A-Frame | Wow Views + Hot Tub
10.0 out of 10, Exceptional, (6)
"Absolutely Stunning Location! Everything in this place is perfect and peaceful!Can’t wait to come back! #AlmostHeaven "
United States
Darrick T.
The price is ￥25,065
￥46,928 total
includes taxes & fees
Dec 17 - Dec 18
Sun Valley Overlook A-Frame | Wow Views + 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.
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Top Shawnee Land Hotel Reviews

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"A fairly new facility conveniently located off the interstate for AA quick overnight stay. Very clean room with good amenities. "
Hollie 1-night trip
Posted 16 hours ago
TRU By Hilton Winchester

Find out more about Shawnee Land

Search for holiday rentals in Shawnee Land on Expedia! You can easily find your home rentals, villas, holiday apartments in Shawnee Land using one of the methods below:

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Look no further and take a look at our great range of rental properties in Shawnee Land!

Frequently asked questions

Can I find a vacation rental in Shawnee Land?

Yes, there are vacation rentals close to well known attractions in Shawnee Land, or you can select a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental in Shawnee Land?

Secluded River Cabin Getaway (Masten Cabin): This vacation home rental outside of Shawnee Land is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What can I see and do in Shawnee Land?

While exploring the area, visit family-friendly sights like Shenandoah Valley Discovery Museum, or get outside and enjoy nature at Shenandoah River. Rock Harbor Golf Course and Valerie Hill Winery are a couple of places you'll find in the larger area.

What are vacation rentals like in Shawnee Land?

Vacation rentals are privately owned accommodations you can reserve for several days or longer in Shawnee Land. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.