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Vacation Homes in Winchester

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, (23)
"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.
$222 nightly
The price is $243
Nov 19 - Nov 20
Total with taxes and fees
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)
"Enjoyed the accommodations. just as advertised would stay again."
United States
Jim S.
$159 nightly
The price is $174
Nov 23 - Nov 24
Total with taxes and fees
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, (89)
"Cute decor, great location and easy to get to. It was a good fit for our weekend stay. "
United States
Sandra C.
$198 nightly
The price is $217
Nov 19 - Nov 20
Total with taxes and fees
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
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.
$337 nightly
The price is $365
Nov 19 - Nov 20
Total with taxes and fees
The Watusi Place - A Modern Umpqua Valley Getaway
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.
$183 nightly
The price is $183
Nov 25 - Nov 26
Total with taxes and fees
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, (12)
"Just as described, clean & comfortable loft bed. Owner great with communication & so nice. Would stay again "
United States
Lucinda H.
$155 nightly
The price is $158
Nov 25 - Nov 26
Total with taxes and fees
Tiny House nestled into the Forest on 160 acre Playground.
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.
$183 nightly
The price is $200
Nov 19 - Nov 20
Total with taxes and fees
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
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.
$293 nightly
The price is $321
Nov 25 - Nov 26
Total with taxes and fees
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.
$159 nightly
The price is $174
Nov 22 - Nov 23
Total with taxes and fees
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
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
$441 nightly
The price is $448
Nov 19 - Nov 20
Total with taxes and fees
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Outdoor spa tub
Private bungalow with AC in charming Roseburg

Private bungalow with AC in charming Roseburg

2.0 star property
Roseburg
$338 nightly
The price is $343
Nov 19 - Nov 20
Total with taxes and fees
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

Hampton Inn & Suites Roseburg

Hampton Inn & Suites Roseburg

10/10 Excellent
"The room was clean and the staff were friendly. Great hotel location close to the concert venue. "
Nancy 1-night trip
Posted 1 day ago
Hampton Inn & Suites Roseburg

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Winchester Vacation Homes information

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