House
10.0(89 Reviews)
2 Bedrooms
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
AU $244/Night
7 Nights - AU $1,705
Winchester Villa Rentals
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Compare Villas, Resorts, & Rentals in Winchester
10.0
House
10.0(2 Reviews)
1 Bedroom
4 Guests
Hot Tub- Parking
Internet
Wellness Facilities
AU $318/Night
7 Nights - AU $2,227
Bed & Breakfast
10.0(53 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $278/Night
7 Nights - AU $1,946
House
10.0(61 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $244/Night
7 Nights - AU $1,710
Bed & Breakfast
9.9(61 Reviews)
1 Bedroom
2 Guests
Breakfast- Parking
Skiing- Balcony/Terrace
AU $425/Night
7 Nights - AU $2,973
House
10.0(25 Reviews)
1 Bedroom
2 Guests
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
AU $314/Night
7 Nights - AU $2,196
Cottage
10.0(8 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
AU $350/Night
7 Nights - AU $2,450
Apartment
10.0(3 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
Laundry
AU $492/Night
7 Nights - AU $3,444
Cottage
10.0(1 Review)
1 Bedroom
2 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
Bedding/Linens
AU $297/Night
7 Nights - AU $2,076
Luxury Places to Stay in Winchester
Over 84+ Luxury Places to Stay in or Near Winchester
House
10.0(9 Reviews)
3 Bedrooms
6 Guests
- Parking
Ocean View- Balcony/Terrace
View
AU $836/Night
7 Nights - AU $5,848
Cabin
10.0(32 Reviews)
5 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $755/Night
7 Nights - AU $5,285
AU $663/Night
7 Nights - AU $4,639
House
9.8(23 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $619/Night
7 Nights - AU $4,332
House
9.6(27 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
Pool- Ocean View
AU $597/Night
7 Nights - AU $4,178
House
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $595/Night
7 Nights - AU $4,165
Apartment
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
AU $556/Night
7 Nights - AU $3,896
House
9.0(9 Reviews)
3 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $534/Night
7 Nights - AU $3,739
House
9.8(26 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $510/Night
7 Nights - AU $3,569
Top-Rated Villas with a Pool in Winchester
Over 19+ Top-Rated Private Villas with a Pool in or Near Winchester
Other
10.0(25 Reviews)
4 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
AU $453/Night
7 Nights - AU $3,170
AU $259/Night
7 Nights - AU $1,810
Hotel
9.6(98 Reviews)
- Breakfast
- Parking
- Pool
- Internet
AU $238/Night
7 Nights - AU $1,666
AU $244/Night
7 Nights - AU $1,706
Hotel
9.0(27 Reviews)
Private Pool- Parking
- Pool
- Internet
AU $237/Night
7 Nights - AU $1,656
AU $240/Night
7 Nights - AU $1,679
AU $150/Night
7 Nights - AU $1,051
AU $175/Night
7 Nights - AU $1,227
AU $154/Night
7 Nights - AU $1,078
Pet-Friendly Villas in Winchester
Over 23+ Pet-Friendly Private Villas in or Near Winchester
House
9.8(27 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $252/Night
7 Nights - AU $1,765
AU $198/Night
7 Nights - AU $1,382
House
10.0(42 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $334/Night
7 Nights - AU $2,339
House
9.6(22 Reviews)
1 Bedroom
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $252/Night
7 Nights - AU $1,765
AU $258/Night
7 Nights - AU $1,805
House
9.6(53 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $260/Night
7 Nights - AU $1,821
Apartment
1 Bedroom
4 Guests
- Internet
Pet Friendly- Laundry
- Bedding/Linens
AU $174/Night
7 Nights - AU $1,219
Apartment
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
AU $94/Night
7 Nights - AU $655
House
10.0(1 Review)
3 Bedrooms
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $973/Night
7 Nights - AU $6,813
Large Private Villas in Winchester
Over 5+ Large Villas in or Near Winchester for Groups and Families
Bed & Breakfast
10.0(22 Reviews)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
AU $421/Night
7 Nights - AU $2,948
House
9.5(93 Reviews)
6 Bedrooms
11 Guests
- Breakfast
- Parking
- Balcony/Terrace
- View
AU $184/Night
7 Nights - AU $1,289
Villa
9.8(7 Reviews)
4 Bedrooms
8 Guests
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
AU $1,288/Night
7 Nights - AU $9,017
House
2.0(1 Review)
4 Bedrooms
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
AU $288/Night
7 Nights - AU $2,018
House
4 Bedrooms
10 Guests
- Air Conditioner
- Internet
- Laundry
- Bedding/Linens
AU $468/Night
7 Nights - AU $3,274
Wheelchair Accessible Holiday Homes in Winchester
Over 11+ Wheelchair Accessible Villas and Holiday Homes in or Near Winchester
AU $135/Night
7 Nights - AU $946
AU $154/Night
7 Nights - AU $1,077
Hotel
7.3(686 Reviews)
- Private Pool
Oceanfront- Hot Tub
EV Charge Station
AU $117/Night
7 Nights - AU $822
AU $123/Night
7 Nights - AU $862
AU $154/Night
7 Nights - AU $1,081
AU $122/Night
7 Nights - AU $852
AU $146/Night
7 Nights - AU $1,022
AU $80/Night
7 Nights - AU $557
AU $101/Night
7 Nights - AU $705
Winchester Villas, Airbnb and Holiday Homes Under $200
Over 27+ Winchester Private Villas, Airbnb and Holiday Homes Under $200
House
9.8(21 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $275/Night
7 Nights - AU $1,923
House
9.5(11 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Internet
Child Friendly
AU $160/Night
7 Nights - AU $1,119
AU $131/Night
7 Nights - AU $920
House
9.6(32 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $287/Night
7 Nights - AU $2,008
House
8.9(21 Reviews)
2 Bedrooms
5 Guests
- Breakfast
- EV Charge Station
- Parking
Spa
AU $215/Night
7 Nights - AU $1,502
House
9.6(10 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $184/Night
7 Nights - AU $1,286
Apartment
1 Bedroom
2 Guests
- Internet
- Child Friendly
- Laundry
- Bedding/Linens
AU $180/Night
7 Nights - AU $1,258
AU $103/Night
7 Nights - AU $721
House
4 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $208/Night
7 Nights - AU $1,456
Instantly Bookable Villa Rentals in Winchester
Over 19+ Instantly Bookable Private Villas in or Near Winchester
House
9.8(109 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $306/Night
7 Nights - AU $2,141
House
9.8(71 Reviews)
1 Bedroom
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $314/Night
7 Nights - AU $2,196
House
9.6(43 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $333/Night
7 Nights - AU $2,328
Apartment
9.4(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $429/Night
7 Nights - AU $3,000
House
10.0(30 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $369/Night
7 Nights - AU $2,583
House
9.8(46 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $321/Night
7 Nights - AU $2,246
House
9.8(42 Reviews)
4 Bedrooms
9 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
AU $447/Night
7 Nights - AU $3,130
House
10.0(24 Reviews)
3 Bedrooms
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $513/Night
7 Nights - AU $3,588
House
10.0(6 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
AU $1,014/Night
7 Nights - AU $7,099
Book a Last Minute Place to Stay in Winchester
About Winchester Vacation Rentals
There are more than 93 incredible getaway rentals that are available in Winchester. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Winchester.
BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Winchester, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Winchester. Places to stay near Winchester are 552.04 ft² on average, with prices averaging AU $320 a night.
BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Winchester. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.
There are 28 hotels in Winchester and 58 rentals
- Prices for a holiday home in Winchester start at AU $80
- Top rated vacation home in Winchester is Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.
- Most popular short term in Winchester is Riverfront Inn Roseburg
- Cheapest place to stay in Winchester is Motel 6-Roseburg, OR
- Most expensive holiday rental in Winchester is Singing Waters at N. Umpqua
Recently Booked Hotels, Resorts, or Rentals in Winchester
Frequently Asked Questions About Winchester?
What are the top hotels or resorts in Winchester?
We provide an array of great vacation destinations in Winchester. If you are looking to stay in or around the Winchester area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Winchester:
- Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.
- Heavenly Bungalow, immaculately clean, close to downtown!
- Historical John Rast House
- Riverfront Log Cabin in Roseburg’s Wine Country
- 4 BEDROOM House across from River in Best Roseburg area!
- Charming 4-bedroom Pearce Historic Farmhouse in Roseburg with AC and WIFI
- Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
- Amazing Mid-Century Modern Home-Incredible Views!
- Singing Waters at N. Umpqua
- Dreamy Hilltop View: Roseburg Retreat w/Hot Tub!
How many vacation rentals have private pools in Winchester?
We have 1 luxury villas and vacation rentals featuriung a private pool in and near Winchester. Some of the best destinations to stay that feature or have access to a swimming pool are:
Which hotel or resort in Winchester is best for families?
Searching for a family-friendly getaway in Winchester? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
How many hotels, resorts, or rentals are available in Winchester?
BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 93 in the Winchester area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Winchester.
