Winchester Vacation Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Winchester vacation rentals

Property grounds

Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (35 reviews)
"Great stay! The place was clean, comfortable, and exactly as described. Host was responsive and helpful. Would definitely stay again."
United States
Wafaa L.
The price is AED 698
AED 875 total
includes taxes & fees
22 Jun - 23 Jun
Blue Mountain Cabin, secluded, perfect for couples, near main road
Interior

Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
The price is AED 489
AED 1,320 total
includes taxes & fees
22 Jun - 23 Jun
Bluemont home just minutes to wineries, breweries, hiking and more!
Exterior

Blue Mountain House - Hot Tub, Grill, Fire Table

Blue Mountain House - Hot Tub, Grill, Fire Table
Linden
The price is AED 588
AED 1,657 total
includes taxes & fees
13 Jul - 14 Jul
Blue Mountain House - Hot Tub, Grill, Fire Table
Terrace/patio

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, (6 reviews)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is AED 533
AED 659 total
includes taxes & fees
24 Jun - 25 Jun
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Fridge, microwave, oven, stovetop

Greek Spa • Private Acreage • Stonefire pizza oven

Greek Spa • Private Acreage • Stonefire pizza oven
Front Royal
The price is AED 323
AED 1,126 total
includes taxes & fees
22 Jun - 23 Jun
Greek Spa • Private Acreage • Stonefire pizza oven
TV

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Front Royal
9.6 out of 10, Exceptional, (17 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is AED 606
AED 871 total
includes taxes & fees
20 Jul - 21 Jul
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Smart TV, books

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester Historic District
8.8 out of 10, Excellent, (5 reviews)
"Large historic house at a great location "
United States
Bryan T.
The price is AED 507
AED 845 total
includes taxes & fees
22 Jun - 23 Jun
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Property grounds

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (45 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is AED 529
AED 1,118 total
includes taxes & fees
23 Jun - 24 Jun
Newly renovated Farm cottage with Mountain views
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (27 reviews)
"We had a great stay! The house is cozy and just perfect for a private get away. The hosts were very communicative and wonderful, we will be back! "
United States
Virginia A.
The price is AED 496
AED 814 total
includes taxes & fees
25 Jun - 26 Jun
Mountain View Bungalow in Front Royal
TV, fireplace, foosball, offices

Delicious Cabin • Wine Country Retreat w/ Hot Tub

Delicious Cabin • Wine Country Retreat w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (11 reviews)
"The cabin was impressive both inside and out. We loved the location and proximity to skyline drive. We would definitely stay here again as it made our trip so much more enjoyable. "
United States
Bill A.
The price is AED 646
AED 1,685 total
includes taxes & fees
28 Jun - 29 Jun
Delicious Cabin • Wine Country Retreat w/ Hot Tub
Dining

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
The price is AED 562
AED 1,398 total
includes taxes & fees
23 Jun - 24 Jun
Comfy Getaway in Strasburg, VA!
Outdoor spa tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (22 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
The price is AED 496
AED 1,414 total
includes taxes & fees
22 Jun - 23 Jun
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Cabin, Private Bathroom (The Pond Cabin) | Exterior

The Pond Cabin

The Pond Cabin
2.0 star property
Linden
The price is AED 878
AED 1,677 total
includes taxes & fees
12 Jul - 13 Jul
The Pond Cabin
Property grounds

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Bluemont
10.0 out of 10, Exceptional, (11 reviews)
"Our stay was great, and we had an excellent time in the area. Short drive to hiking spots and within walking distance to the local Bluemont Station restaurant. Highly recommend this stay in a quaint location!"
United States
Nicholas B.
The price is AED 519
AED 1,061 total
includes taxes & fees
22 Jun - 23 Jun
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Property grounds

The Haven at Turkey Run • Hot Tub, Fire Pit, Games

The Haven at Turkey Run • Hot Tub, Fire Pit, Games
Strasburg
10.0 out of 10, Exceptional, (14 reviews)
"Loved the creek and the hot tub!!! Cant say enough good things about this place"
United States
Maxx H.
The price is AED 639
AED 1,661 total
includes taxes & fees
15 Jul - 16 Jul
The Haven at Turkey Run • Hot Tub, Fire Pit, Games
Terrace/patio

Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
9.6 out of 10, Exceptional, (8 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 traveler
The price is AED 367
AED 645 total
includes taxes & fees
2 Jul - 3 Jul
Cozy English Basement Apt quiet but close to downtown
Interior

Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
10.0 out of 10, Exceptional, (31 reviews)
"It was a great place to stay and very clean."
United States
Chynna V.
The price is AED 694
AED 1,572 total
includes taxes & fees
24 Jun - 25 Jun
Mountain cabin near national park & wineries
Fridge, microwave, oven, stovetop

The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.8 out of 10, Good, (7 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
The price is AED 345
AED 762 total
includes taxes & fees
22 Jun - 23 Jun
The Queen of Winchester Three Bedroom with Upper Level Deck
Shower

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.0 out of 10, Wonderful, (9 reviews)
"Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. "
United States
Haley M.
The price is AED 496
AED 992 total
includes taxes & fees
29 Jun - 30 Jun
Lunar Loft, with mountain views
Fridge, stovetop, coffee/tea maker, lobster pot

Buena Vista

Buena Vista
Shawneeland
The price is AED 386
AED 863 total
includes taxes & fees
7 Jul - 8 Jul
Buena Vista
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 Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

8/10 Good
"Overall Good Stay for short stay"
Sathish Kumar 1-night trip
Posted 8 hours ago
La Quinta Inn & Suites by Wyndham Winchester

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals in Winchester near Shenandoah Valley Discovery Museum, or you can go with a secluded option if you want a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theater scene while you're visiting.

What are some of the best vacation home rentals in Winchester?

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.: This vacation home rental near Winchester offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Winchester?

Choose from 14 Expedia vacation rentals in Winchester for a memorable vacation.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of family-friendly sights, whereas cultural attractions include Bright Box Theater and Winchester Little Theater. Other places in town to visit include Patsy Cline Historic House and Museum of the Shenandoah Valley.

What’s a vacation rental in Winchester like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winchester. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for family trips.