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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winchester holiday rentals

A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

1. Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
10.0 out of 10, Exceptional, (1 review)
"Beautiful flat! We loved our time there"
United States
Daniel
The price is HK$2,227
HK$3,040 total
includes taxes & fees
13 Oct - 14 Oct
Bell Sister Flats
A modern house with a stone pathway leading to the entrance, surrounded by various plants and a large planter.

2. 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, (33 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$863
HK$1,564 total
includes taxes & fees
13 Oct - 14 Oct
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
A small, single-story house with a green door, white trim, and a small porch.

3. 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, (45 reviews)
"Nice place, great location."
United States
Gordon
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
A house with a covered porch, a seating area with a sofa and armchair, and a small table.

4. <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, (118 reviews)
"Great stay, very clean. Would stay here again."
United States
Cindan G.
The price is HK$942
HK$1,650 total
includes taxes & fees
13 Oct - 14 Oct
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
A wooden deck with a white railing, a potted plant, and a table.

5. 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, (25 reviews)
"Beautiful property and incredible stay. Not only was the room clean, private and super comfortable, the hosts were amazing. They made my comfort a priority every day! Definitely would give it a 5 star rating, I will recommend it to family and friends."
United States
Betty W.
The price is HK$1,562
HK$1,959 total
includes taxes & fees
1 Nov - 2 Nov
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

6. Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
10.0 out of 10, Exceptional, (3 reviews)
"Bell Sister Flats is amazing - so gorgeous, warm and inviting. We loved being on Main Street and walking to coffee, dinner, drinks. So much attention to detail and such comfort provided from the bed to the sheets to the towels and love seat and, oh the shower! Terry and Paul were wonderful hosts, so attentive and generous. Loved that they promoted the local community with goods and services in the flat. Loved our stay!"
United States
Tara T.
The price is HK$1,719
HK$2,844 total
includes taxes & fees
13 Oct - 14 Oct
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
A serene outdoor seating area with string lights, overlooking a body of water and a mountainous backdrop.

7. Private Umpqua River Retreat w/ 2 King Suites & Patio

Private Umpqua River Retreat w/ 2 King Suites & Patio
Roseburg
10.0 out of 10, Exceptional, (8 reviews)
Private Umpqua River Retreat w/ 2 King Suites & Patio
A small house with a porch and string lights.

8. Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (30 reviews)
"Close to downtown, well appointed, clean and comfortable. Thanks for a lovely stay!"
United States
Sue S.
The price is HK$636
HK$1,298 total
includes taxes & fees
18 Oct - 19 Oct
Downtown Stay at the Red Tiny Twin!
A wooden cabin with a deck, outdoor seating, and a pathway lit by ground lights.

9. 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, (19 reviews)
"Great location, nice and quiet easy to get to fantastic hosts."
United States
Lee and Kristy D.
The price is HK$832
HK$1,083 total
includes taxes & fees
4 Nov - 5 Nov
Tiny House nestled into the Forest on 160 acre Playground.
A wooden cabin named 'Lil Cedar Lodge' with a metal roof, two windows, and a small porch with a chair and table.

10. Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
10.0 out of 10, Exceptional, (3 reviews)
"Awesome place. Really enjoyed my stay."
United States
Zakary S.
The price is HK$746
HK$956 total
includes taxes & fees
4 Nov - 5 Nov
Lil Cedar Lodge
A living room with a sofa, a coffee table, a fireplace, a TV, and a painting on the wall.

11. Home Sweet Home

Home Sweet Home
Sutherlin
9.0 out of 10, Wonderful, (12 reviews)
"This location worked great for our visit with family in the area. The house was clean and the beds were comfortable. Host was easy to work with - thanks!"
United States
Barbara S.
The price is HK$942
HK$2,750 total
includes taxes & fees
10 Nov - 11 Nov
Home Sweet Home
A spacious living area with a wooden dining table, black chairs, a ceiling fan, and a television displaying a beach scene.

12. The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (59 reviews)
"Great place for us and the kids after a long day at the wildlife safari!"
United States
Jessica M.
The price is HK$1,271
HK$3,040 total
includes taxes & fees
13 Oct - 14 Oct
The Watusi Place - A Modern Umpqua Valley Getaway
A storefront with a black awning displaying the names 'Bell Sister Flats' and 'Paul L Bentley Architect A.I.A. P.C.' with contact numbers and a door marked '615'.

13. Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
The price is HK$1,876
HK$3,033 total
includes taxes & fees
13 Oct - 14 Oct
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
A wooden pathway leading to a covered area with a view of a mountainous landscape.

14. 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, (50 reviews)
"We only had one night to stay here but it is one we would definitely stay at again. It was clean, bright, stocked with everything needed (no oven or range top but did have a toaster oven). It was very comfortable for us and our 2 dogs and very charming. We really enjoyed our quick visit. The only thing that could be an issue was there was a lot of steps to get down to the house which could be an issue for those with any mobility problems. The steps light up as you use them at night which was...
United States
cynthia
The price is HK$1,388
HK$1,548 total
includes taxes & fees
13 Oct - 14 Oct
Charming, Private Cottage near I-5 and Golf Course.
A modern house with a gravel driveway, large windows, and a view of a forest.

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

Lone Rock Guest House, 20 acres minutes from the North Umpqua River
Glide
10.0 out of 10, Exceptional, (2 reviews)
"I have stayed at probably 100 rental houses in my life - this is hands down my favorite and was best suited for my outdoor boys. There are endless things to do on the property and you are in the center of an outdoor adventure town with lakes, rivers, hikes, waterfalls, fishing and more. It was private, clean, well stocked, comfortable and high quality - and the host was responsive, welcoming and helpful. Thank you for the memories. I hope we can come back for an even longer stay next time."
United States
Secret L.
The price is HK$2,535
HK$4,700 total
includes taxes & fees
24 Oct - 25 Oct
Lone Rock Guest House, 20 acres minutes from the North Umpqua River
A bathroom with a shower curtain, a towel rack, a water heater, and a striped towel.

16. Elk Meadow Hideaway LLC Minutes away Worlds apart

Elk Meadow Hideaway LLC Minutes away Worlds apart
Myrtle Creek
The price is HK$848
HK$1,020 total
includes taxes & fees
13 Oct - 14 Oct
Elk Meadow Hideaway LLC Minutes away Worlds apart
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

8/10 Good
"Convenient place to stop on the way to california. A little old but clean."
Daniel 1-night trip
Posted 1 hour ago
Riverfront Inn Roseburg

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:

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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?

Private Umpqua River Retreat w/ 2 King Suites & Patio: This holiday home rental outside of Winchester is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.