Winchester Holiday Rentals

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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Winchester holiday rentals

Terrace/patio

Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
The price is HK$668
HK$877 total
includes taxes & fees
20 Feb - 21 Feb
Lil Cedar Lodge
Property grounds

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$1,247
HK$1,405 total
includes taxes & fees
20 Feb - 21 Feb
Charming, Private Cottage near I-5 and Golf Course.
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, (43 reviews)
"Enjoyed our stay!"
United States
Dana M.
The price is HK$742
HK$1,292 total
includes taxes & fees
24 Feb - 25 Feb
A Restful Studio Near a Creek and Forest - Pets
Exterior

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$977
HK$1,806 total
includes taxes & fees
1 Mar - 2 Mar
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
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, (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$1,516
HK$1,831 total
includes taxes & fees
20 Mar - 21 Mar
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
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
Roseburg
9.6 out of 10, Exceptional, (53 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is HK$860
HK$1,412 total
includes taxes & fees
18 Feb - 19 Feb
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Dining

The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (48 reviews)
"Home was well stocked and was very accessible to our winery we belong to. "
United States
Amy W.
The price is HK$1,161
HK$2,760 total
includes taxes & fees
22 Feb - 23 Feb
The Watusi Place - A Modern Umpqua Valley Getaway
Living area

Home Sweet Home

Home Sweet Home
Sutherlin
8.6 out of 10, Excellent, (10 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$938
HK$2,619 total
includes taxes & fees
17 Mar - 18 Mar
Home Sweet Home
Exterior detail

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$860
HK$1,540 total
includes taxes & fees
20 Mar - 21 Mar
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Exterior

<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)
"We had a great stay! The house was amazing, and peaceful. We would definitely stay again. "
United States
Ashley D.
The price is HK$938
HK$1,626 total
includes taxes & fees
20 Mar - 21 Mar
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
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, (13 reviews)
"Wonderful environment and very peaceful stay. "
United States
Sarah C.
The price is HK$900
HK$1,231 total
includes taxes & fees
28 Feb - 1 Mar
Tiny House nestled into the Forest on 160 acre Playground.
Dining

Charming cottage studio in serene environment perfect for a relaxing getaway

Charming cottage studio in serene environment perfect for a relaxing getaway
Winston
The price is HK$1,250
HK$1,428 total
includes taxes & fees
20 Mar - 21 Mar
Charming cottage studio in serene environment perfect for a relaxing getaway
Private kitchen

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is HK$2,244
HK$3,056 total
includes taxes & fees
19 Feb - 20 Feb
Bell Sister Flats
Exterior

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$668
HK$1,331 total
includes taxes & fees
18 Feb - 19 Feb
Downtown Stay at the Red Tiny Twin!
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
Glide
The price is HK$2,524
HK$4,680 total
includes taxes & fees
20 Mar - 21 Mar
Lone Rock Guest House, 20 acres minutes from the North Umpqua River
Living area

Grove Stay

Grove Stay
Sutherlin
The price is HK$1,094
HK$1,891 total
includes taxes & fees
18 Feb - 19 Feb
Grove Stay
Fridge, microwave, oven, stovetop

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)
"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$1,712
HK$2,687 total
includes taxes & fees
20 Mar - 21 Mar
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Outdoor dining

Private bungalow with AC in charming Roseburg

Private bungalow with AC in charming Roseburg
Roseburg
The price is HK$2,368
HK$2,753 total
includes taxes & fees
2 Mar - 3 Mar
Private bungalow with AC in charming Roseburg
Exterior detail

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$1,868
HK$3,013 total
includes taxes & fees
1 Mar - 2 Mar
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
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

Comfort Inn Roseburg

Comfort Inn Roseburg

10/10 Excellent
"Yes"
William 1-night trip
Posted 3 days ago
Comfort Inn Roseburg

Find out more about Winchester

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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?

Singing Waters at N. Umpqua: This highly rated holiday home rental in Winchester is located on the beach, and has a balcony, a BBQ and air conditioning 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. Melrose Vineyards and Reustle Prayer Rock 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.