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Check prices for these dates

Next weekend
12 Dec - 14 Dec
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19 Dec - 21 Dec
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2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Vacation Homes in Winchester

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)
"Great place! The only thing I’d change is some blackout curtains if folks wanted to sleep in! Otherwise everything was amazing, Very sweet host and not to mention the beautiful property! "
United Kingdom
Hunter S.
The price is SAR 413
SAR 680 total
includes taxes & fees
4 Dec - 5 Dec
A Restful Studio Near a Creek and Forest - Pets
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, (13)
"Just as described, clean & comfortable loft bed. Owner great with communication & so nice. Would stay again "
United States
Lucinda H.
The price is SAR 432
SAR 591 total
includes taxes & fees
3 Dec - 4 Dec
Tiny House nestled into the Forest on 160 acre Playground.
Exterior
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

Roseburg
9.6 out of 10, Exceptional, (36)
"Nice place, great location."
United States
Gordon
The price is SAR 469
SAR 859 total
includes taxes & fees
28 Dec - 29 Dec
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Terrace/patio
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Roseburg
10.0 out of 10, Exceptional, (24)
"My parents stayed here for our son's graduation. They were very impressed with the hosts and warm welcome they received"
United States
SharonLee S.
The price is SAR 728
SAR 912 total
includes taxes & fees
3 Dec - 4 Dec
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Exterior
Red Tiny Twins, Downtown Eco & Pet Friendly Stay

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

Roseburg
9.6 out of 10, Exceptional, (19)
"It was a perfect place for us to stay for a short trip to visit family with our two little dogs."
United States
Rochelle S.
The price is SAR 357
SAR 682 total
includes taxes & fees
5 Dec - 6 Dec
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
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, (90)
"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 SAR 488
SAR 834 total
includes taxes & fees
11 Dec - 12 Dec
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
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, (37)
"Just as advertised! Great house. Would definitely stay there again."
United States
Jake G.
The price is SAR 445
SAR 1,075 total
includes taxes & fees
14 Dec - 15 Dec
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
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 SAR 357
SAR 678 total
includes taxes & fees
4 Dec - 5 Dec
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
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, (47)
"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 SAR 557
SAR 1,370 total
includes taxes & fees
3 Dec - 4 Dec
The Watusi Place - A Modern Umpqua Valley Getaway
Private kitchen
Home Sweet Home

Home Sweet Home

Sutherlin
8.6 out of 10, Excellent, (10)
"We really enjoyed our stay! There are super comfortable beds, comfortable couch, fantastic washing machine, nice front porch and clean kitchen! The host was communicative and friendly ! Would for sure recommend and will stay there again on our next trip! "
United States
A T.
The price is SAR 450
SAR 575 total
includes taxes & fees
3 Dec - 4 Dec
Home Sweet Home
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 certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
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, (18)
"This property was very enjoyable for the children and I enjoyed the kitchen."
United States
Stacy B.
The price is SAR 811
SAR 1,680 total
includes taxes & fees
9 Dec - 10 Dec
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Dining
Lone Rock Guest House, 20 acres minutes from the North Umpqua River

Lone Rock Guest House, 20 acres minutes from the North Umpqua River

2.0 star property
Glide
The price is SAR 922
SAR 1,926 total
includes taxes & fees
26 Dec - 27 Dec
Lone Rock Guest House, 20 acres minutes from the North Umpqua River
Outdoor spa tub
Private bungalow with AC in charming Roseburg

Private bungalow with AC in charming Roseburg

2.0 star property
Roseburg
The price is SAR 1,137
SAR 1,288 total
includes taxes & fees
2 Jan - 3 January 2026
Private bungalow with AC in charming Roseburg
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

Riverfront Inn Roseburg

Riverfront Inn Roseburg

10/10 Excellent
"I was pleased they had left the lights on for our after dark arrival. The pet area was convenient to the room and really nice. I will stay again. "
Julie 1-night trip
Posted 2 days ago
Riverfront Inn Roseburg