Book Holiday Homes in Winchester

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Featured Holiday Homes in Winchester

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
The price is NZ$530 per night from 5 Jan to 6 Jan
NZ$530
includes taxes & fees
5 Jan - 6 Jan 2025
Book a stay at this family-friendly vacation home in Roseburg. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Stewart Park and Douglas ...
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
A Restful Studio Near a Creek and Forest - Pets

A Restful Studio Near a Creek and Forest - Pets

Roseburg
The price is NZ$292 per night from 5 Jan to 6 Jan
NZ$292
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this vacation home in Douglas County. Enjoy balconies, an in-room coffeemaker, and housekeeping.
A Restful Studio Near a Creek and Forest - Pets
The Bucket List Retreat

The Bucket List Retreat

Roseburg
The price is NZ$789 per night from 5 Jan to 6 Jan
NZ$789
includes taxes & fees
5 Jan - 6 Jan 2025
Book a stay at this golf vacation home in Roseburg. Enjoy free WiFi, a garden, and patios. Popular attractions Stewart Park and Douglas County Museum of History ...
The Bucket List Retreat
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Indigo Collective - Modern Home

Indigo Collective - Modern Home

Roseburg
The price is NZ$845 per night from 5 Jan to 6 Jan
NZ$845
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this vacation home in Roseburg. Enjoy air conditioning. Popular attractions Stewart Park and Douglas County Museum of History and Natural History are ...
Indigo Collective - Modern Home
<br>~Keasington House, a Mid Century Gem in Hucrest.  2bdrm, 2bath

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

Roseburg
The price is NZ$389 per night from 22 Jan to 23 Jan
NZ$389
includes taxes & fees
22 Jan - 23 Jan 2025
Book a stay at this family-friendly vacation home in Roseburg. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Stewart Park ...
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Cozy Roseburg Home w/ Fire Pit + Gas Grill!

Cozy Roseburg Home w/ Fire Pit + Gas Grill!

Roseburg
Stay at this vacation home in Roseburg. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Douglas County Museum of History and Natural ...
Cozy Roseburg Home w/ Fire Pit + Gas Grill!
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

Roseburg
The price is NZ$405 per night from 8 Jan to 9 Jan
NZ$405
includes taxes & fees
8 Jan - 9 Jan 2025
Stay at this vacation home in Roseburg. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Stewart Park and Douglas County Museum of History ...
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
The Farmhouse on the North Umpqua River

The Farmhouse on the North Umpqua River

Glide
Stay at this vacation home in Idleyld Park. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attraction Little River is located nearby.
The Farmhouse on the North Umpqua River
The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

Winston
The price is NZ$647 per night from 3 Jan to 4 Jan
NZ$647
includes taxes & fees
3 Jan - 4 Jan 2025
Stay at this vacation home in Winston. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Abacela Winery and Wildlife Safari are located ...
The Watusi Place - A Modern Umpqua Valley Getaway
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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.

Winchester Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winchester vacation homes are the perfect way for you to wing it.

Holiday houses in Winchester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winchester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winchester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winchester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winchester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winchester Holiday Homes essential information

Accommodation
39 Holiday Homes
Lowest Price
NZ$140
Highest Price
NZ$845
Popular accommodation
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun, A Restful Studio Near a Creek and Forest - Pets, The Bucket List Retreat, Indigo Collective - Modern Home,
~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath, Cozy Roseburg Home w/ Fire Pit + Gas Grill!, The Urban Boho Charmer with Private Backyard, BBQ & Hammock, The Farmhouse on the North Umpqua River, The Watusi Place - A Modern Umpqua Valley Getaway

Top trending hotels in Winchester

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Roseburg North
Stay at this vacation home in Roseburg North. Enjoy a beach locale, balconies, and an in-room coffeemaker. Popular attractions Winchester Dam and Becker Vineyard ...
Singing Waters at N. Umpqua
Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave, Roseburg, OR
Fully refundableReserve now, pay when you stay
The price is NZ$181 per night from 23 Dec to 24 Dec
NZ$181
includes taxes & fees
23 Dec - 24 Dec
Stay at this motel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Riverfront Inn Roseburg
Comfort Inn Roseburg

Comfort Inn Roseburg

2.5 out of 5
1539 NW Mullholland Drive, Roseburg, OR
Fully refundableReserve now, pay when you stay
The price is NZ$173 per night from 24 Dec to 25 Dec
NZ$173
includes taxes & fees
24 Dec - 25 Dec
Book a stay at this golf hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Comfort Inn Roseburg
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Sleep Inn & Suites Roseburg North Near Medical Center

Sleep Inn & Suites Roseburg North Near Medical Center

2.5 out of 5
2855 NW Edenbower Blvd, Roseburg, OR
Fully refundableReserve now, pay when you stay
The price is NZ$140 per night from 5 Jan to 6 Jan
NZ$140
includes taxes & fees
5 Jan - 6 Jan 2025
Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Sleep Inn & Suites Roseburg North Near Medical Center
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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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^Subject to availability and chosen travel dates.