Winchester Holiday Rentals

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in Winchester

Interior
Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Roseburg North
10.0 out of 10, Exceptional, (8)
"Extremely relaxing. Beautifully done house on the North Umpqua River. Just lovely. Look forward to future stays!"
United States
Joanna D.
Singing Waters at N. Umpqua
Fridge, microwave, oven, stovetop
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Roseburg North
9.4 out of 10, Exceptional, (16)
"great property"
United States
Mai
The price is HK$1,679
HK$3,527 total
includes taxes & fees
19 Nov - 20 Nov
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Fridge, microwave, oven, stovetop
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

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

Roseburg
9.6 out of 10, Exceptional, (51)
"It was a great place, super close proximity to grocery stores and the airport which is where I needed to be each day for work. "
United States
Dana M.
The price is HK$972
HK$1,558 total
includes taxes & fees
19 Nov - 20 Nov
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Exterior
Heavenly Bungalow, immaculately clean, close to downtown!

Heavenly Bungalow, immaculately clean, close to downtown!

Roseburg
10.0 out of 10, Exceptional, (48)
"Nice place to stay. "
United States
Janine
Heavenly Bungalow, immaculately clean, close to downtown!
Exterior
Tiny House nestled into the Forest on 160 acre Playground.

Tiny House nestled into the Forest on 160 acre Playground.

Roseburg
9.6 out of 10, Exceptional, (12)
"Just as described, clean & comfortable loft bed. Owner great with communication & so nice. Would stay again "
United States
Lucinda H.
The price is HK$896
HK$1,225 total
includes taxes & fees
28 Nov - 29 Nov
Tiny House nestled into the Forest on 160 acre Playground.
Exterior detail
Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.

Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.

Roseburg
10.0 out of 10, Exceptional, (75)
"Another great stay!This is my second year staying at this property. It is located in a very quiet neighborhood. The home is kept very clean and is well stocked. We hope to be back next year!Thanks!"
United States
Susan B.
Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.
Fridge, microwave, oven, stovetop
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

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

Roseburg
9.8 out of 10, Exceptional, (36)
"This place is great. We have stayed multiple times. Will continue to come back here when in the area. "
United States
Benjamin B.
The price is HK$867
HK$2,252 total
includes taxes & fees
25 Nov - 26 Nov
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Fridge, microwave, oven, stovetop
Family home

Family home

Roseburg
9.8 out of 10, Exceptional, (8)
"I would suggest to everyone to stay here!"
United States
Kendal M.
Family home
Interior
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

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

Roseburg
9.8 out of 10, Exceptional, (89)
"Cute decor, great location and easy to get to. It was a good fit for our weekend stay. "
United States
Sandra C.
The price is HK$972
HK$1,685 total
includes taxes & fees
19 Nov - 20 Nov
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Outdoor dining
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

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

Roseburg
9.4 out of 10, Exceptional, (24)
"It was nice."
United States
Al N.
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Property entrance
River Vista Vacation Homes

River Vista Vacation Homes

3.0 star property
Idleyld Park
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!"
United States
Emily
River Vista Vacation Homes
Terrace/patio
A Restful Studio Near a Creek and Forest - Pets

A Restful Studio Near a Creek and Forest - Pets

Roseburg
10.0 out of 10, Exceptional, (40)
"Extremely comfortable! Beautiful accommodations. "
United States
Ruby G.
The price is HK$855
HK$1,425 total
includes taxes & fees
4 Dec - 5 Dec
A Restful Studio Near a Creek and Forest - Pets
Outdoor dining
The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

Winston
10.0 out of 10, Exceptional, (46)
"The house was amazing! Easy to get in, clean and well stocked. Definitely recommend to anyone looking for a nice place."
United States
Amy H.
The price is HK$1,154
HK$2,838 total
includes taxes & fees
19 Nov - 20 Nov
The Watusi Place - A Modern Umpqua Valley Getaway
Property grounds
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water

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

Idleyld Park
9.8 out of 10, Exceptional, (57)
"great nature location, the river was fun to swim at "
United States
Ami S.
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water
Interior
Southern Oregon Cabin: Fire Pit & Private Pond!

Southern Oregon Cabin: Fire Pit & Private Pond!

3.0 star property
Oakland
10.0 out of 10, Exceptional, (1)
"Cute little place! Especially liked the patio and outside areas. Inside needs a few finishing touches like coat hooks on back of doors, but place is very new, clean and worked great for our few days there."
United States
Wayne
Southern Oregon Cabin: Fire Pit & Private Pond!
1 bedroom, bed sheets
Lil Cedar Lodge

Lil Cedar Lodge

Roseburg
The price is HK$665
HK$872 total
includes taxes & fees
25 Nov - 26 Nov
Lil Cedar Lodge
Fridge, microwave, oven, stovetop
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Winston
9.6 out of 10, Exceptional, (60)
"This was amazing stay. Great location, close to every place we wanted to go. It was very nice and clean. We will definitely be staying again. "
United States
Gina C.
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Property grounds
the Bunkhouse coyote- Private Studio Retreat Room

the Bunkhouse coyote- Private Studio Retreat Room

2.0 star property
Winston
10.0 out of 10, Exceptional, (1)
"The views are out of this world! The horses on property are gorgeous! This truly felt like a vacation within a vacation (drove that way for the wildlife safari park). We plan to come back again! Property owner is a sweetheart! "
United States
Charles B.
The price is HK$595
HK$919 total
includes taxes & fees
19 Nov - 20 Nov
the Bunkhouse coyote- Private Studio Retreat Room
Interior
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Roseburg
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."
United States
John L.
The price is HK$692
HK$1,353 total
includes taxes & fees
3 Dec - 4 Dec
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Private kitchen
Bell Sister Flats

Bell Sister Flats

2.0 star property
Roseburg
The price is HK$1,945
HK$2,726 total
includes taxes & fees
19 Nov - 20 Nov
Bell Sister Flats
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

Comfort Inn Roseburg

Comfort Inn Roseburg

10/10 Excellent
"Clean nice staff "
SALLY 1-night trip
Posted 2 days ago
Comfort Inn Roseburg

Find out more about Winchester

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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 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 a coffee maker.

What’s there to see and do in Winchester?

While exploring the area, visit family-friendly sights like Wildlife Safari, or get outside and enjoy nature at North Umpqua River. Melrose Vineyards and Reustle Prayer Rock 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.