Holiday Homes in Winchester

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Featured Holiday Homes in Winchester and around

Terrace/patio
A Restful Studio Near a Creek and Forest - Pets
A Restful Studio Near a Creek and Forest - Pets
10.0 out of 10, Exceptional, (37)
"Peaceful and clean."
The price is €146
includes taxes & fees
19 Oct - 20 Oct
A Restful Studio Near a Creek and Forest - Pets
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!
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"
The price is €156
includes taxes & fees
1 Nov - 2 Nov
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
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
9.8 out of 10, Exceptional, (34)
"This place is great. We have stayed multiple times. Will continue to come back here when in the area. "
The price is €260
includes taxes & fees
19 Oct - 20 Oct
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
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 €153
includes taxes & fees
18 Oct - 19 Oct
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Exterior
Tiny House nestled into the Forest on 160 acre Playground.
Tiny House nestled into the Forest on 160 acre Playground.
9.4 out of 10, Exceptional, (10)
"Just as described, clean & comfortable loft bed. Owner great with communication & so nice. Would stay again "
The price is €139
includes taxes & fees
17 Oct - 18 Oct
Tiny House nestled into the Forest on 160 acre Playground.
Private kitchen
Home Sweet Home
Home Sweet Home
9.6 out of 10, Exceptional, (5)
"Truly enjoyed staying at "Home Sweet Home". Beds are very comfortable, home was very clean, hosts were quick to respond and give info through texts. Would definitely recommend staying here. Looking for a great place to stay while check out the wineries? You found the place."
The price is €195
includes taxes & fees
29 Oct - 30 Oct
Home Sweet Home
Exterior
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
9.6 out of 10, Exceptional, (19)
"Enjoyed the accommodations. just as advertised would stay again."
The price is €153
includes taxes & fees
17 Oct - 18 Oct
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Exterior
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
9.6 out of 10, Exceptional, (34)
"Nice place, great location."
The price is €191
includes taxes & fees
27 Oct - 28 Oct
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Interior
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
<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 €192
includes taxes & fees
19 Oct - 20 Oct
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
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
9.6 out of 10, Exceptional, (49)
"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 €205
includes taxes & fees
19 Oct - 20 Oct
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Outdoor dining
The Watusi Place - A Modern Umpqua Valley Getaway
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 €394
includes taxes & fees
11 Nov - 12 Nov
The Watusi Place - A Modern Umpqua Valley Getaway
Fridge, microwave, oven, stovetop
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
9.4 out of 10, Exceptional, (13)
"great property"
The price is €397
includes taxes & fees
17 Oct - 18 Oct
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
4 bedrooms, iron/ironing board, Internet, bed sheets
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
Lone Rock Guest House, 20 acres minutes from the North Umpqua River
Outdoor dining
Private bungalow with AC in charming Roseburg
Private bungalow with AC in charming Roseburg
2.0 star property
The price is €311
includes taxes & fees
30 Oct - 31 Oct
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 staff was incredible. They were kind to our little family, and made us feel right at home."
Andrew 1-night trip
Posted 4 days ago
Hampton Inn & Suites Roseburg

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
372
Accommodation
43 Holiday Homes
Lowest Price
€139
Highest Price
€397

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