Winchester Holiday Rentals
Cottage
- Winchester
- ·
- Paris
- 2.18 mi to center
9.8Exceptional
(54 Reviews)
1 Bedroom
1 Bath
2 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $263/Night
7 Nights - US $1,840
House
- Winchester
- ·
- Front Royal
- 7.78 mi to center
10.0Exceptional
(4 Reviews)
4 Bedrooms
3 Baths
8 Guests
2497.23 ft²
Hot Tub- Parking
- Balcony/Terrace
View
US $386/Night
7 Nights - US $2,702
Hotel
- Winchester
- ·
- Front Royal
- 2.95 mi to center
9.6Exceptional
(600 Reviews)
1 Bath
Breakfast- Parking
Pool- Balcony/Terrace
US $155/Night
7 Nights - US $1,087
Cabin
- Winchester
- ·
- Front Royal
- 8.81 mi to center
8.8Fabulous
(10 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $255/Night
7 Nights - US $1,783
House
- Winchester
- ·
- Front Royal
- 8.83 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Hot Tub
- Breakfast
EV Charge Station- Parking
US $356/Night
7 Nights - US $2,490
House
- Winchester
- ·
- Paris
- 1.92 mi to center
10.0Exceptional
(13 Reviews)
4 Bedrooms
2 Baths
9 Guests
2300 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $402/Night
7 Nights - US $2,817
Villa
- Winchester
- ·
- Paris
- 2.36 mi to center
10.0Exceptional
(2 Reviews)
6 Bedrooms
6 Baths
13 Guests
10000 ft²
Private Pool- Parking
- Pool
- Balcony/Terrace
US $2,372/Night
7 Nights - US $16,603
Cabin
- Winchester
- ·
- Paris
- 2.53 mi to center
9.6Exceptional
(8 Reviews)
3 Bedrooms
1 Bath
7 Guests
2500 ft²
- Parking
- Kitchen
- Air Conditioner
Internet
US $527/Night
7 Nights - US $3,692
House
- Winchester
- ·
- Chester Gap
- 0.77 mi to center
10.0Exceptional
(112 Reviews)
2 Bedrooms
2 Baths
6 Guests
1800 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $661/Night
7 Nights - US $4,625
Luxury Holiday Rentals in Winchester
Over 433+ Luxury Holiday Rentals in or Near Winchester
House
- Winchester
- ·
- Bluemont
- 1.56 mi to center
10.0Exceptional
(33 Reviews)
7 Bedrooms
8 Baths
16 Guests
10000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $2,567/Night
7 Nights - US $17,966
Villa
- Winchester
- ·
- Paris
- 2.36 mi to center
6 Bedrooms
7 Baths
13 Guests
9999.67 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $1,910/Night
7 Nights - US $13,370
Cabin
- Winchester
- ·
- Front Royal
- 2.50 mi to center
4 Bedrooms
3 Baths
8 Guests
- Air Conditioner
- Internet
Child Friendly
Laundry
US $1,860/Night
7 Nights - US $13,018
House
- Winchester
- ·
- Bluemont
- 4.30 mi to center
10.0Exceptional
(84 Reviews)
5 Bedrooms
6 Baths
14 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,322/Night
7 Nights - US $9,255
House
- Winchester
- ·
- Stephens City
- 4.83 mi to center
3 Bedrooms
2 Baths
6 Guests
1377.78 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- View
US $1,068/Night
7 Nights - US $7,474
House
- Winchester
- ·
- Bluemont
- 2.61 mi to center
9.4Exceptional
(10 Reviews)
6 Bedrooms
4 Baths
14 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,029/Night
7 Nights - US $7,200
House
- Winchester
- ·
- Berryville
- 5.29 mi to center
8.4Excellent
(7 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $919/Night
7 Nights - US $6,432
Villa
- Winchester
- ·
- Front Royal
- 7.43 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
1323.96 ft²
- Hot Tub
- EV Charge Station
- Parking
- Balcony/Terrace
US $914/Night
7 Nights - US $6,396
New
Cabin
- Winchester
- ·
- Bluemont
- 1.92 mi to center
5 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Air Conditioner
- Internet
Pet Friendly
US $852/Night
7 Nights - US $5,962
Top-Rated Holiday Rentals with a Pool in Winchester
Over 58+ The Best Private Villas and Holiday Rentals in Winchester with a Pool
Ski Chalet
- Winchester
- ·
- Front Royal
- 8.89 mi to center
10.0Exceptional
(58 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Hot Tub
- Parking
- Pool
Ocean View
US $354/Night
7 Nights - US $2,479
Cabin
- Winchester
- ·
- Front Royal
- 2.84 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
3 Baths
8 Guests
2200 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $447/Night
7 Nights - US $3,132
Other
- Winchester
- ·
- Boyce
- 1.04 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $330/Night
7 Nights - US $2,308
House
- Winchester
- ·
- Front Royal
- 0.82 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
1 Bath
10 Guests
2088 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $514/Night
7 Nights - US $3,601
Hotel
- Virginia
- ·
- Winchester
- 2.69 mi to center
9.4Exceptional
(1017 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $108/Night
7 Nights - US $755
Hotel
- Winchester
- ·
- Old Town Winchester
- 0.18 mi to center
9.4Exceptional
(1003 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
Spa
US $148/Night
7 Nights - US $1,034
Hotel
- Virginia
- ·
- Winchester
- 3.29 mi to center
9.4Exceptional
(894 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $126/Night
7 Nights - US $885
Hotel
- Winchester
- ·
- White Post
- 1.63 mi to center
9.4Exceptional
(180 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Spa
US $275/Night
7 Nights - US $1,923
Hotel
- Virginia
- ·
- Winchester
- 1.80 mi to center
9.2Exceptional
(2288 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $129/Night
7 Nights - US $903
Pet-Friendly Holiday Rentals in Winchester
Over 201+ Pet-Friendly Holiday Rentals in or Near Winchester
Cabin
- Winchester
- ·
- Bluemont
- 1.07 mi to center
10.0Exceptional
(47 Reviews)
1 Bedroom
1 Bath
2 Guests
1249 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $265/Night
7 Nights - US $1,853
House
- Winchester
- ·
- Berryville
- 3.89 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
6 Guests
4380.91 ft²
- Parking
- Internet
- Pet Friendly
Wellness Facilities
US $444/Night
7 Nights - US $3,106
Apartment
- Virginia
- ·
- Winchester
- 0.22 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $289/Night
7 Nights - US $2,022
Cabin
- Winchester
- ·
- Berryville
- 4.82 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $245/Night
7 Nights - US $1,714
House
- Winchester
- ·
- Paris
- 2.36 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
7 Guests
2497.23 ft²
Oceanfront- Parking
- Ocean View
- View
US $401/Night
7 Nights - US $2,805
Cabin
- Winchester
- ·
- Berryville
- 4.63 mi to center
9.0Exceptional
(14 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $177/Night
7 Nights - US $1,241
Cabin
- Winchester
- ·
- Bluemont
- 2.61 mi to center
7.6Very Good
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $218/Night
7 Nights - US $1,529
Apartment
- Winchester
- ·
- Berryville
- 0.86 mi to center
7.4Very Good
(9 Reviews)
1 Bedroom
1 Bath
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $237/Night
7 Nights - US $1,660
Apartment
- Winchester
- ·
- Berryville
- 0.83 mi to center
7.2Very Good
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $258/Night
7 Nights - US $1,807
Large Holiday Rentals and Private Villas in Winchester
Over 53+ Large Holiday Rentals and Private Villas in or Near Winchester
House
- Winchester
- ·
- Strasburg
- 0.47 mi to center
10.0Exceptional
(12 Reviews)
5 Bedrooms
3 Baths
10 Guests
2761 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $323/Night
7 Nights - US $2,262
House
- Virginia
- ·
- Winchester
- 4.91 mi to center
9.8Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
10 Guests
2002.09 ft²
- Parking
- Air Conditioner
- Internet
Sports/Activities
US $239/Night
7 Nights - US $1,672
House
- Winchester
- ·
- Strasburg
- 1.49 mi to center
10.0Exceptional
(4 Reviews)
5 Bedrooms
2 Baths
13 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $282/Night
7 Nights - US $1,971
Bed & Breakfast
- Winchester
- ·
- Front Royal
- 3.81 mi to center
9.5Exceptional
(209 Reviews)
3 Bedrooms
3 Baths
11 Guests
290.63 ft²
- Breakfast
- Parking
Skiing- Balcony/Terrace
US $184/Night
7 Nights - US $1,288
Villa
- Winchester
- ·
- Bluemont
- 1.33 mi to center
10.0Exceptional
(60 Reviews)
4 Bedrooms
3 Baths
8 Guests
4000 ft²
- Internet
- Pet Friendly
- Child Friendly
- Sports/Activities
US $800/Night
7 Nights - US $5,598
House
- Winchester
- ·
- Front Royal
- 8.02 mi to center
10.0Exceptional
(46 Reviews)
3 Bedrooms
3 Baths
10 Guests
3000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $278/Night
7 Nights - US $1,945
House
- Winchester
- ·
- Chester Gap
- 1.13 mi to center
10.0Exceptional
(32 Reviews)
5 Bedrooms
4 Baths
8 Guests
7707 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $536/Night
7 Nights - US $3,755
Ski Chalet
- Winchester
- ·
- Front Royal
- 6.21 mi to center
10.0Exceptional
(6 Reviews)
4 Bedrooms
2 Baths
11 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $364/Night
7 Nights - US $2,546
House
- Virginia
- ·
- Winchester
- 1.63 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
2 Baths
10 Guests
4700 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $751/Night
7 Nights - US $5,254
Wheelchair Accessible Holiday Homes in Winchester
Over 41+ Wheelchair Accessible Holiday Homes in or Near Winchester
House
- Winchester
- ·
- Front Royal
- 7.75 mi to center
9.5Exceptional
(9 Reviews)
4 Bedrooms
3 Baths
8 Guests
2400.35 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Air Conditioner
US $271/Night
7 Nights - US $1,898
Hotel
- Virginia
- ·
- Winchester
- 4.83 mi to center
9.4Exceptional
(1129 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $120/Night
7 Nights - US $837
House
- Winchester
- ·
- Front Royal
- 7.69 mi to center
4 Bedrooms
3 Baths
8 Guests
2497.23 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Air Conditioner
US $241/Night
7 Nights - US $1,685
Hotel
- Winchester
- ·
- Old Town Winchester
- 2.56 mi to center
9.2Exceptional
(1440 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Air Conditioner
US $116/Night
7 Nights - US $813
Hotel
- Virginia
- ·
- Winchester
- 1.39 mi to center
9.2Exceptional
(410 Reviews)
6 Baths
290.63 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $110/Night
7 Nights - US $769
Hotel
- Virginia
- ·
- Winchester
- 1.25 mi to center
9.2Exceptional
(1019 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $87/Night
7 Nights - US $611
Hotel
- Virginia
- ·
- Winchester
- 1.97 mi to center
9.2Exceptional
(85 Reviews)
3 Baths
419.79 ft²
- Breakfast
- EV Charge Station
- Parking
- Air Conditioner
US $142/Night
7 Nights - US $991
Hotel
- Virginia
- ·
- Winchester
- 1.91 mi to center
9.1Exceptional
(156 Reviews)
13 Baths
390.81 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
US $156/Night
7 Nights - US $1,090
Hotel
- Virginia
- ·
- Winchester
- 2.72 mi to center
9.0Exceptional
(349 Reviews)
1 Bath
247.57 ft²
- Private Pool
- EV Charge Station
- Parking
- Pool
US $125/Night
7 Nights - US $874
Winchester Private Villas and Holiday Homes Under $200
Over 134+ Winchester Private Villas and Holiday Homes Under $200
New
Cottage
- Virginia
- ·
- Winchester
- 0.64 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $159/Night
7 Nights - US $1,114
Apartment
- Winchester
- ·
- Front Royal
- 3.84 mi to center
9.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
904.17 ft²
- Parking
- Internet
- Pet Friendly
- Sports/Activities
US $158/Night
7 Nights - US $1,106
Hotel
- Virginia
- ·
- Winchester
- 2.24 mi to center
9.4Exceptional
(22 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $106/Night
7 Nights - US $741
House
- Virginia
- ·
- Winchester
- 0.82 mi to center
10.0Exceptional
(60 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $138/Night
7 Nights - US $964
House
- Winchester
- ·
- Front Royal
- 1.50 mi to center
8.6Fabulous
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
904.17 ft²
- Parking
- Balcony/Terrace
- Internet
- Pet Friendly
US $155/Night
7 Nights - US $1,088
Cabin
- Winchester
- ·
- Stephens City
- 3.88 mi to center
10.0Exceptional
(13 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $184/Night
7 Nights - US $1,286
Apartment
- Winchester
- ·
- Front Royal
- 0.98 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $149/Night
7 Nights - US $1,045
Apartment
- Winchester
- ·
- Front Royal
- 5.66 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $169/Night
7 Nights - US $1,181
House
- Winchester
- ·
- Front Royal
- 1.50 mi to center
9.6Exceptional
(33 Reviews)
2 Bedrooms
1 Bath
4 Guests
908 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $169/Night
7 Nights - US $1,180
Instantly Bookable Holiday Homes in Winchester
Over 223+ Instantly Bookable Holiday Homes in or Near Winchester
House
- Winchester
- ·
- Berryville
- 4.78 mi to center
8.0Excellent
(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $262/Night
7 Nights - US $1,834
Condo
- Winchester
- ·
- Stephens City
- 1.95 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $231/Night
7 Nights - US $1,615
Other
- Winchester
- ·
- Berryville
- 0.97 mi to center
6.8Good
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Kitchen
- Internet
- Child Friendly
Bedding/Linens
US $265/Night
7 Nights - US $1,857
House
- Winchester
- ·
- Berryville
- 3.89 mi to center
10.0Exceptional
(46 Reviews)
4 Bedrooms
3 Baths
6 Guests
4384 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $511/Night
7 Nights - US $3,580
Cabin
- Winchester
- ·
- Paris
- 1.45 mi to center
10.0Exceptional
(22 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $556/Night
7 Nights - US $3,891
Cabin
- Winchester
- ·
- Front Royal
- 9.78 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
8 Guests
9903 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $479/Night
7 Nights - US $3,352
Cottage
- Winchester
- ·
- Berryville
- 1.48 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $239/Night
7 Nights - US $1,673
Cottage
- Winchester
- ·
- Boyce
- 2.71 mi to center
9.6Exceptional
(38 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $264/Night
7 Nights - US $1,846
House
- Winchester
- ·
- Berryville
- 4.80 mi to center
8.8Fabulous
(15 Reviews)
3 Bedrooms
2 Baths
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $277/Night
7 Nights - US $1,942
Book a Last Minute Place to Stay in Winchester
About Casai's Private Villas and Holiday Rentals in Winchester
Discover more than 442 vacation rentals available in Winchester. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winchester.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winchester, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winchester. On average, places to stay near Winchester offer 985.76 ft², with nightly prices averaging US $345.
With Casai, finding and comparing holiday rentals in Winchester is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Winchester
| Type | Count |
|---|---|
| Vacation Homes | 179 |
| Holiday Apartments | 68 |
| Cottages | 24 |
| Villas | 10 |
Use these Quick Filters to Find a Holiday Rental in Winchester
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Winchester.
Weather in Winchester, VA
View the weather forecast for Winchester before booking your Winchester Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Winchester, VA
Casai offers a large selection of top attractions around Winchester . Research things to do on your vacation before you visit Winchester.
Other Places to Stay in Winchester, VA
Frequently Asked Questions About Winchester?
What are the top holiday rentals in Winchester?
With numerous options available in Winchester, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winchester:
- Don't Overlook this One! The View belongs to You!
- Fantasy Cottage: Private Pond, Waterfall, Hot Tub
- Spacious Cabin on Cedar Creek, Shenandoah Forest Immersion!
- Take a Break from Chaos at Rolling River Holidays
- Whiskey Hill Cabin a mountain escape in Virginia wine country!
- Country Elegance overlooking the Shenandoah River
- The Nest at Chester Gap
- 6 Bedroom Farmhouse Owned by Bear Chase
- Bear Mountain Lodge Shenandoah Mountains Skyline Drive/Front Royal (hottub)
- Highmeadows Estate in the heart of Bluemont Virginia
How many holiday rentals have private pools in Winchester?
Discover a selection of holiday rentals with private pools near Winchester with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Stunning Former Winery w/Pool & Mtn Views!
- SpringHill Suites Winchester
- Stunning Bluemont Manor with 9 Bedrooms 7 Baths
- Stunning Former Winery With Mountain Views
Which holiday homes in Winchester are best for families?
If you're searching for a family-friendly holiday home in Winchester, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winchester:
- Mountain View + Hot tub + Sauna + Yoga + Trails + Wineries + Geodesic stargazing dome
- Rivers Edge - On the River, Breathtaking views!
- Hampton Inn Front Royal
How many Casai.com holiday rentals are available in Winchester?
As of 2026, Casai boasts over 442 properties listed in the Winchester area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winchester.
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