Winchester Holiday Rentals

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Holiday Rentals in Winchester

Singing Waters at N. Umpqua
Interior

Singing Waters at N. Umpqua

10.0 out of 10, Exceptional, (8)
"Extremely relaxing. Beautifully done house on the North Umpqua River. Just lovely. Look forward to future stays!"
Singing Waters at N. Umpqua
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Fridge, microwave, oven, stovetop

Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

9.8 out of 10, Exceptional, (33)
"Extremely clean home in a safe neighborhood! We had everything we needed! Host was very kind and communicative! Would love to stay there again! "
The price is HK$931
HK$2,280 total
includes taxes & fees
6 Oct - 7 Oct
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Firewater Lodge Cabin Experience
Outdoor dining

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (62)
"Wonderful property,had everything we needed,Thankyou again"
Firewater Lodge Cabin Experience
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Fridge, microwave, oven, stovetop

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

9.8 out of 10, Exceptional, (48)
"Bill's house was comfortable, and the house and property were consistent with the listing. The house and furnishings worked well for my family for our one-night stay."
The price is HK$1,167
HK$1,807 total
includes taxes & fees
15 Oct - 16 Oct
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Exterior

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (33)
"Nice place, great location."
The price is HK$895
HK$1,687 total
includes taxes & fees
3 Oct - 4 Oct
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
The Watusi Place - A Modern Umpqua Valley Getaway
Outdoor dining

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (46)
"This house is great for a family trip to the Wildlife Safari! The location is perfect and the property is suited to accommodate all ages with plenty of room to spread out. Family games, a place to grill, large kitchen and attention to detail from the cleaning team. "
The price is HK$1,296
HK$3,036 total
includes taxes & fees
7 Oct - 8 Oct
The Watusi Place - A Modern Umpqua Valley Getaway
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Interior

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.4 out of 10, Exceptional, (19)
"Just the right size and location for a wine country getaway weekend. Had everything we needed, and more. Will not hesitate to book again next trip, if it's available."
The price is HK$693
HK$1,355 total
includes taxes & fees
15 Oct - 16 Oct
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Interior

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

9.8 out of 10, Exceptional, (88)
"It was wonderful to go back in time, furniture, turn table all brought back delightful memories of my childhood. Thanks for sharing your place with us. "
The price is HK$973
HK$1,687 total
includes taxes & fees
19 Oct - 20 Oct
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Lil Cedar Lodge
1 bedroom, bed sheets

Lil Cedar Lodge

The price is HK$635
HK$842 total
includes taxes & fees
4 Oct - 5 Oct
Lil Cedar Lodge
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Outdoor dining

Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

9.4 out of 10, Exceptional, (23)
"Very clean and we loved how well stocked it was! Thankful for the garage to park in! Easy to find and easy to check in!"
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water
Property grounds

River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water

9.8 out of 10, Exceptional, (57)
"Amazing!"
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water
A Restful Studio Near a Creek and Forest - Pets
Terrace/patio

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (37)
"Peaceful and clean."
The price is HK$739
HK$1,286 total
includes taxes & fees
4 Oct - 5 Oct
A Restful Studio Near a Creek and Forest - Pets
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Fridge, microwave, oven, stovetop

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.4 out of 10, Exceptional, (12)
"great property"
The price is HK$1,681
HK$3,484 total
includes taxes & fees
2 Oct - 3 Oct
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Tiny House nestled into the Forest on 160 acre Playground.
Exterior

Tiny House nestled into the Forest on 160 acre Playground.

9.4 out of 10, Exceptional, (9)
"The property was as described. Quiet and beautiful location. My partner and I had a magical time on our mini vacation!"
The price is HK$897
HK$1,226 total
includes taxes & fees
4 Oct - 5 Oct
Tiny House nestled into the Forest on 160 acre Playground.
Indigo Collective - Modern Comfort & Bold Design
Microwave, oven, stovetop, dishwasher

Indigo Collective - Modern Comfort & Bold Design

10.0 out of 10, Exceptional, (22)
"We had a lovely 3 generation family visit. "
Indigo Collective - Modern Comfort & Bold Design
Family home
Fridge, microwave, oven, stovetop

Family home

9.6 out of 10, Exceptional, (4)
"I would suggest to everyone to stay here!"
Family home
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Exterior

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

9.8 out of 10, Exceptional, (17)
"Enjoyed the accommodations. just as advertised would stay again."
The price is HK$693
HK$1,355 total
includes taxes & fees
8 Oct - 9 Oct
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Bell Sister Flats
Private kitchen

Bell Sister Flats

2.0 star property
The price is HK$2,593
HK$3,436 total
includes taxes & fees
31 Oct - 1 Nov
Bell Sister Flats
River Vista Vacation Homes
Property entrance

River Vista Vacation Homes

3.0 star property
9.2 out of 10, Wonderful, (45)
"The place was right on the river which was beautiful and it had everything that we would need. It was clean and pretty roomy for my family and I to spend the weekend there and we absolutely loved it! We’re already trying to make another trip out here!"
River Vista Vacation Homes
Home Sweet Home
Private kitchen

Home Sweet Home

9.6 out of 10, Exceptional, (5)
Home Sweet Home
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

Quality Inn Central Roseburg

Quality Inn Central Roseburg

10/10 Excellent
"Front desk very welcoming. Clean, perfect size property. Great breakfast. Loved the pool."
Andrea 1-night trip
Posted 3 days ago
Quality Inn Central Roseburg

Find out more about Winchester

Find out more about Winchester

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

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

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

Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its restaurants.

What are some of the best holiday rentals that Winchester has to offer?

River Vista Vacation Homes: This holiday home rental outside of Winchester is located on a river, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like Douglas County Museum of History and Natural History, or get outside and enjoy nature at North Umpqua River. Stewart Park and Melrose Vineyards are a couple of places you'll find in the wider area.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip.