Winchester Vacation Rentals & Ski-in/Ski-out Homes
House
- Ohio
- ·
- Fort Recovery
- 3.20 mi to center
10.0Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
14 Guests
Parking
Kitchen
Air Conditioner
Internet
US $432/Night
7 Nights - US $3,024
House
10.0Exceptional
(4 Reviews)
1 Bedroom
2 Baths
7 Guests
1700.7 ft²
- Parking
Balcony/Terrace
View- Air Conditioner
US $128/Night
7 Nights - US $898
Cottage
1 Bedroom
1 Bath
- Kitchen
- Internet
Pet Friendly
Child Friendly
US $320/Night
7 Nights - US $2,238
House
- Indiana
- ·
- Linn Grove
- 21.05 mi to center
10.0Exceptional
(223 Reviews)
7 Bedrooms
4 Baths
28 Guests
3219 ft²
Private Pool
Hot Tub- Parking
Pool
US $1,224/Night
7 Nights - US $8,568
House
9.8Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
Spa- Balcony/Terrace
- Child Friendly
US $310/Night
7 Nights - US $2,172
Cabin
10.0Exceptional
(24 Reviews)
4 Bedrooms
3 Baths
12 Guests
2100 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $924/Night
7 Nights - US $6,469
House
- Ohio
- ·
- Fort Recovery
- 2.91 mi to center
10.0Exceptional
(24 Reviews)
3 Bedrooms
2 Baths
8 Guests
1364 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $333/Night
7 Nights - US $2,333
New
House
3 Bedrooms
2 Baths
5 Guests
1286 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $340/Night
7 Nights - US $2,382
New
House
10.0Exceptional
(49 Reviews)
4 Bedrooms
3 Baths
10 Guests
3264 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $470/Night
7 Nights - US $3,293
Luxury Places to Stay in Winchester
Over 262+ Luxury Places to Stay in or Near Winchester
House
10.0Exceptional
(7 Reviews)
6 Bedrooms
7 Baths
23 Guests
12000 ft²
- Parking
- Pool
Ocean View- Balcony/Terrace
US $2,742/Night
7 Nights - US $19,197
House
- Indiana
- ·
- Delaware County
- 7.30 mi to center
10.0Exceptional
(10 Reviews)
4 Bedrooms
3 Baths
11 Guests
3099 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,403/Night
7 Nights - US $9,820
House
- Indiana
- ·
- Delaware County
- 6.71 mi to center
4 Bedrooms
4 Baths
8 Guests
- Balcony/Terrace
- Kitchen
Security/Safety
US $1,149/Night
7 Nights - US $8,044
House
8.0Excellent
(1 Review)
5 Bedrooms
3 Baths
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $832/Night
7 Nights - US $5,821
House
10.0Exceptional
(11 Reviews)
4 Bedrooms
4 Baths
14 Guests
3000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $779/Night
7 Nights - US $5,455
House
- Muncie
- ·
- New Castle
- 5.12 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
3000 ft²
- Ocean View
- View
- Kitchen
- Air Conditioner
US $650/Night
7 Nights - US $4,548
House
1 Bedroom
4 Baths
12 Guests
2077.43 ft²
Oceanfront- Parking
- Pool
- Ocean View
US $637/Night
7 Nights - US $4,461
New
House
6 Bedrooms
2 Baths
19 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $617/Night
7 Nights - US $4,320
House
- Indiana
- ·
- Delaware County
- 5.21 mi to center
9.0Exceptional
(9 Reviews)
5 Bedrooms
2 Baths
18 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $606/Night
7 Nights - US $4,243
Top-Rated Vacation Rentals with a Pool in Winchester
Over 47+ Top-Rated Vacation Rentals with a Pool in or Near Winchester
Hotel
- Sidney
- ·
- Versailles
- 2.04 mi to center
9.6Exceptional
(125 Reviews)
1 Bath
Breakfast- Parking
- Pool
- Balcony/Terrace
US $293/Night
7 Nights - US $2,053
Hotel
9.4Exceptional
(786 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $113/Night
7 Nights - US $790
Hotel
9.4Exceptional
(73 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Air Conditioner
US $137/Night
7 Nights - US $958
Hotel
9.4Exceptional
(24 Reviews)
1 Bath
428.76 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Air Conditioner
US $163/Night
7 Nights - US $1,142
Hotel
9.3Exceptional
(83 Reviews)
7 Baths
322.92 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $103/Night
7 Nights - US $723
Hotel
9.2Exceptional
(988 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $132/Night
7 Nights - US $926
Hotel
9.2Exceptional
(459 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $141/Night
7 Nights - US $990
Hotel
9.2Exceptional
(389 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $115/Night
7 Nights - US $808
Hotel
9.1Exceptional
(249 Reviews)
4 Baths
462.85 ft²
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $125/Night
7 Nights - US $873
Pet-Friendly Vacation Rentals in Winchester
Over 73+ Pet-Friendly Vacation Rentals in or Near Winchester
Apartment
10.0Exceptional
(152 Reviews)
1 Bedroom
1 Bath
2 Guests
151 ft²
- Kitchen
- Air Conditioner
- Pet Friendly
- Child Friendly
US $68/Night
7 Nights - US $479
House
- Sidney
- ·
- Greenville
- 0.74 mi to center
9.6Exceptional
(11 Reviews)
3 Bedrooms
1 Bath
6 Guests
1054.86 ft²
- Parking
- Internet
- Pet Friendly
Sports/Activities
US $281/Night
7 Nights - US $1,967
Hotel
7.0Very Good
(965 Reviews)
1 Bath
- Parking
- Kitchen
- Air Conditioner
- Internet
US $55/Night
7 Nights - US $387
Apartment
10.0Exceptional
(115 Reviews)
1 Bedroom
1 Bath
4 Guests
151 ft²
- Kitchen
- Air Conditioner
- Pet Friendly
- Child Friendly
US $116/Night
7 Nights - US $811
House
9.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
957.99 ft²
- Parking
- Internet
- Pet Friendly
- Security/Safety
US $175/Night
7 Nights - US $1,223
House
- Indiana
- ·
- Delaware County
- 1.32 mi to center
10.0Exceptional
(12 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $222/Night
7 Nights - US $1,552
House
10.0Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
4 Guests
960 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $167/Night
7 Nights - US $1,172
House
- Muncie
- ·
- New Castle
- 1.68 mi to center
10.0Exceptional
(9 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $322/Night
7 Nights - US $2,254
House
- Sidney
- ·
- Greenville
- 1.72 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $244/Night
7 Nights - US $1,706
Large Vacation Homes & Villas in Winchester
Over 19+ Large Vacation Homes & Villas in or Near Winchester
House
- Sidney
- ·
- Greenville
- 0.44 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
2 Baths
12 Guests
2200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $374/Night
7 Nights - US $2,615
Villa
8.0Excellent
(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
1700.7 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $309/Night
7 Nights - US $2,165
House
9.8Exceptional
(40 Reviews)
8 Bedrooms
3 Baths
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $333/Night
7 Nights - US $2,328
House
3 Bedrooms
2 Baths
10 Guests
2529.52 ft²
- Parking
- Internet
- Child Friendly
Laundry
US $292/Night
7 Nights - US $2,045
House
9.8Exceptional
(20 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $337/Night
7 Nights - US $2,359
Cottage
- Richmond
- ·
- Spring Grove
- 0.05 mi to center
9.4Exceptional
(36 Reviews)
5 Bedrooms
2 Baths
12 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
- Child Friendly
US $223/Night
7 Nights - US $1,560
House
9.0Exceptional
(17 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $329/Night
7 Nights - US $2,305
House
- Richmond
- ·
- Centerville
- 0.15 mi to center
8.4Excellent
(6 Reviews)
5 Bedrooms
6 Baths
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $427/Night
7 Nights - US $2,988
House
- Indiana
- ·
- Delaware County
- 4.96 mi to center
7.6Very Good
(4 Reviews)
3 Bedrooms
1 Bath
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $409/Night
7 Nights - US $2,866
Wheelchair Accessible Vacation Homes in Winchester
Over 31+ Wheelchair Accessible Vacation Homes in or Near Winchester
Hotel
9.1Exceptional
(147 Reviews)
8 Baths
236.8 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $153/Night
7 Nights - US $1,070
Hotel
9.0Exceptional
(928 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $123/Night
7 Nights - US $860
Hotel
- Sidney
- ·
- Greenville
- 2.31 mi to center
9.0Exceptional
(64 Reviews)
6 Baths
322.92 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
US $114/Night
7 Nights - US $798
Hotel
9.0Exceptional
(549 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $129/Night
7 Nights - US $903
Hotel
8.7Fabulous
(132 Reviews)
13 Baths
322.92 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $132/Night
7 Nights - US $926
Hotel
- Muncie
- ·
- Winchester
- 1.02 mi to center
8.8Fabulous
(275 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $121/Night
7 Nights - US $847
Hotel
- Sidney
- ·
- Greenville
- 2.32 mi to center
8.7Fabulous
(110 Reviews)
1 Bath
322.92 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $116/Night
7 Nights - US $814
Hotel
8.6Fabulous
(359 Reviews)
1 Bath
247.57 ft²
- Private Pool
- Parking
- Pool
- Kitchen
US $117/Night
7 Nights - US $816
Hotel
8.6Fabulous
(141 Reviews)
6 Baths
380.33 ft²
- Private Pool
- Breakfast
- Parking
- Pool
US $232/Night
7 Nights - US $1,622
Winchester Resorts and Airbnb Homes Under $200
Over 137+ Winchester Resorts and Airbnb Homes Under $200
House
10.0Exceptional
(38 Reviews)
2 Bedrooms
1 Bath
4 Guests
850 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $181/Night
7 Nights - US $1,266
House
7.5Very Good
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1194.79 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $136/Night
7 Nights - US $950
Hotel
9.2Exceptional
(457 Reviews)
1 Bath
- Parking
- Kitchen
- Air Conditioner
- Internet
US $89/Night
7 Nights - US $626
House
10.0Exceptional
(30 Reviews)
1 Bedroom
1 Bath
2 Guests
360 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $156/Night
7 Nights - US $1,092
Apartment
- Indiana
- ·
- Hagerstown
- 0.07 mi to center
1.0Average
(1 Review)
1 Bedroom
1 Bath
4 Guests
1205.56 ft²
- Parking
- Internet
- Security/Safety
Guest Services
US $121/Night
7 Nights - US $847
Cottage
10.0Exceptional
(17 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $142/Night
7 Nights - US $992
Apartment
- Indiana
- ·
- Hagerstown
- 0.16 mi to center
10.0Exceptional
(16 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $165/Night
7 Nights - US $1,152
Cabin
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
170 ft²
- Kitchen
- Air Conditioner
- Internet
TV
US $181/Night
7 Nights - US $1,269
House
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $160/Night
7 Nights - US $1,118
Instantly Bookable Vacation Homes in Winchester
Over 101+ Instantly Bookable Vacation Homes in or Near Winchester
New
House
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $322/Night
7 Nights - US $2,255
House
4 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $357/Night
7 Nights - US $2,501
Condo
- Muncie
- ·
- New Castle
- 0.09 mi to center
10.0Exceptional
(40 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $212/Night
7 Nights - US $1,486
Condo
10.0Exceptional
(25 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $344/Night
7 Nights - US $2,409
House
- Muncie
- ·
- New Castle
- 1.71 mi to center
10.0Exceptional
(25 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $237/Night
7 Nights - US $1,661
House
- Indiana
- ·
- Delaware County
- 7.22 mi to center
10.0Exceptional
(15 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $227/Night
7 Nights - US $1,592
Apartment
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
1400 ft²
- Parking
- Ocean View
- View
- Kitchen
US $305/Night
7 Nights - US $2,132
House
- Sidney
- ·
- Greenville
- 1.61 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $343/Night
7 Nights - US $2,401
Cabin
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
1 Guest
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $328/Night
7 Nights - US $2,297
Book a Last Minute Place to Stay in Winchester
About Winchester Vacation Rentals
Explore over 271 vacation rentals in Winchester with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Winchester for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Winchester. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Winchester tailored to your preferences. On average, these rentals offer 563.77 ft² of space, and are priced at an average of US $243 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Winchester at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Winchester
| Type | Count |
|---|---|
| Vacation Homes | 128 |
| Holiday Apartments | 37 |
| Cabin Rentals | 9 |
| Cottages | 4 |
| Others | 2 |
| Villas | 2 |
| Unique Vacation Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Winchester
★ Pro Tip: Discover Your Ideal Vacation Rental in Winchester with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Winchester, IN
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, IN
Sunski 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, IN
Frequently Asked Questions About Winchester?
What are the top vacation rentals in Winchester?
When organizing your trip to Winchester, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Winchester. Peruse our collection of highly-rated properties and secure your reservation today.
- Indoor Gymnasium, Seasonal Pool, 7 Bedroom, Sleeps 28
- King Bed Non-Smoking
- 2 Queen Beds Non-Smoking
- Recently remodeled Colonial-style home with room for the whole family!
- Downtown New Castle Indiana Condo for short-and long-term stays. Very popular.
- Top-Rated Home Near Ball State & IU Hospital- Top Guest Pick!
- Settle in at the Petite Retreat.
- 'Downtown Delight' w/Patio! 1 Mi to Ball State
- Entire Home with Modern Conveniences - New Castle
- Heated Seasonal Pool, Hot Tub & Theater Rustic Cabin by Bike Path
How many vacation rentals have private pools in Winchester?
Uncover 15 vacation rentals boasting private pools near Winchester. Explore top-rated RBO homes offering access to a swimming pool:
- Cozy Cabin with fireplace, hot tub & hiking trails
- Home2 Suites By Hilton Richmond
- Side B Private Entry Sleeps 6 Kayaks Firepit River Access
- Harmony Hideaway Over 4000 sqft, 5 mins to BSU & IU, Games Rooms and Summer Pool
Which vacation homes or resorts in Winchester are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Winchester. Enjoy great views, locations and save money with SunSki Resorts.™
- Newly Renovated, Quiet Home
- New Castle Getaway with Fireplace Garage & Near Attractions-Family Friendly
- 'downtown Delight' w/Patio! 1 Mi to Ball State
How many SunSkiResorts vacation rentals or resorts are available in Winchester?
Discover the ideal vacation rental in Winchester with SunSki Resorts™. We provide an extensive selection of over 271 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Winchester.
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