Winchester Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Winchester holiday rentals

Terrace/patio
A Restful Studio Near a Creek and Forest - Pets

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 reviews)
"Amazing!!"
United Kingdom
Maureen S.
The price is HK$740
HK$1,288 total
includes taxes & fees
12 Jan - 13 Jan
A Restful Studio Near a Creek and Forest - Pets
Terrace/patio
Lil Cedar Lodge

Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
The price is HK$666
HK$874 total
includes taxes & fees
11 Jan - 12 Jan
Lil Cedar Lodge
Exterior
Tiny House nestled into the Forest on 160 acre Playground.

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 reviews)
"Wonderful environment and very peaceful stay. "
United States
Sarah C.
The price is HK$898
HK$1,228 total
includes taxes & fees
11 Jan - 12 Jan
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

The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Roseburg
9.6 out of 10, Exceptional, (37 reviews)
"Nice place, great location."
United States
Gordon
The price is HK$974
HK$1,767 total
includes taxes & fees
11 Jan - 12 Jan
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Smart TV, fireplace, books, music library
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

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, (39 reviews)
"We had a great stay while we visited family. The house had everything we needed, and the new mattresses were very comfortable. Gary was easy to get ahold of and responded quickly. We would stay again. "
United States
Riley E.
The price is HK$926
HK$2,388 total
includes taxes & fees
11 Jan - 12 Jan
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Living area
Home Sweet Home

Home Sweet Home

Home Sweet Home
Sutherlin
8.6 out of 10, Excellent, (10 reviews)
"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 HK$935
HK$2,680 total
includes taxes & fees
12 Jan - 13 Jan
Home Sweet Home
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!

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Roseburg
10.0 out of 10, Exceptional, (24 reviews)
"Absolutely the most delightful and magical place to stay! Wonderfully gracious hosts! They made our honeymoon stay spectacular and special! James and Gail are fabulous. We had the most incredible breakfast as well. We felt like royalty! "
United States
Rachel S.
The price is HK$1,512
HK$1,843 total
includes taxes & fees
10 Feb - 11 Feb
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Dining
The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (47 reviews)
"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$1,157
HK$2,837 total
includes taxes & fees
14 Jan - 15 Jan
The Watusi Place - A Modern Umpqua Valley Getaway
TV, books
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Roseburg
9.6 out of 10, Exceptional, (29 reviews)
"Finding the entry to the property was hardest part. Parking was OK. The views and the space was great. Nice central location for many places to visit."
United States
Nicole B.
The price is HK$857
HK$1,536 total
includes taxes & fees
11 Jan - 12 Jan
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Smart TV
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

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, (52 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is HK$857
HK$1,416 total
includes taxes & fees
21 Jan - 22 Jan
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Exterior
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

<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, (91 reviews)
"Thank you so much for the comfy cozy place to stay! "
United States
Kristina C.
The price is HK$1,013
HK$1,715 total
includes taxes & fees
18 Jan - 19 Jan
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Exterior detail
Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.4 out of 10, Exceptional, (19 reviews)
"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$740
HK$1,408 total
includes taxes & fees
1 Feb - 2 Feb
Downtown Stay at the Blue Tiny Twin
Fridge, microwave, oven, stovetop
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
2.0 star property
Roseburg
10.0 out of 10, Exceptional, (3 reviews)
"Terry's place was such a treat! The apartment exceeded so many of our expectations and was perfect for our mini vacation. Wonderful features and amenities. Beautiful finishes, linens and furnishings. Super responsive host. We look forward to our next stay!"
United States
CARISSA F.
The price is HK$1,551
HK$2,578 total
includes taxes & fees
11 Jan - 12 Jan
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Outdoor dining
Cozy 1-bedroom house in adorable Roseburg with AC

Cozy 1-bedroom house in adorable Roseburg with AC

Cozy 1-bedroom house in adorable Roseburg with AC
2.0 star property
Roseburg
The price is HK$655
HK$1,451 total
includes taxes & fees
31 Jan - 1 Feb
Cozy 1-bedroom house in adorable Roseburg with AC
Property grounds
Charming, Private Cottage near I-5 and Golf Course.

Charming, Private Cottage near I-5 and Golf Course.

Charming, Private Cottage near I-5 and Golf Course.
Myrtle Creek
10.0 out of 10, Exceptional, (42 reviews)
"This is the second time I have stayed here, both times with my dog. The place is convenient, quiet, clean, comfortable, and with great touches and landscaping outside. Wonderful place."
United States
Carter L.
The price is HK$1,243
HK$1,401 total
includes taxes & fees
10 Feb - 11 Feb
Charming, Private Cottage near I-5 and Golf Course.
Exterior detail
Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (21 reviews)
"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 HK$740
HK$1,408 total
includes taxes & fees
5 Feb - 6 Feb
Downtown Stay at the Red Tiny Twin!
Private kitchen
Bell Sister Flats

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is HK$2,077
HK$2,872 total
includes taxes & fees
14 Jan - 15 Jan
Bell Sister Flats
Interior
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

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, (19 reviews)
"This property was very enjoyable for the children and I enjoyed the kitchen."
United States
Stacy B.
The price is HK$2,105
HK$3,972 total
includes taxes & fees
14 Jan - 15 Jan
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Exterior
Lone Rock Guest House, 20 acres minutes from the North Umpqua River

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
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

Private bungalow with AC in charming Roseburg
2.0 star property
Roseburg
The price is HK$2,362
HK$2,745 total
includes taxes & fees
12 Jan - 13 Jan
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

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?


~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath: This holiday home rental outside of Winchester offers a selection of games, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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. Stewart Park and Melrose 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.