Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Singing Waters at N. Umpqua

10.0 out of 10, Exceptional, (6)
"Extremely relaxing. Beautifully done house on the North Umpqua River. Just lovely. Look forward to future stays!"
Singing Waters at N. Umpqua

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

9.8 out of 10, Exceptional, (82)
"Love this little abode and recommend "
The price is €191
includes taxes & fees
31 Aug - 1 Sept
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Home Sweet Home

10.0 out of 10, Exceptional, (2)
"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."
Home Sweet Home

Tiny House nestled into the Forest on 160 acre Playground.

9.4 out of 10, Exceptional, (9)
"It was such a nice little spot to get away."
The price is €139
includes taxes & fees
14 Aug - 15 Aug
Tiny House nestled into the Forest on 160 acre Playground.

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (61)
"This place was amazing and we will be going back for sure. Peaceful and relaxing setting. Home is beautiful and has everything you will need. "
Firewater Lodge Cabin Experience

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (28)
"We have stayed at this property now multiple times and it has been clean, easy, great location, everything works and we will definitely be back"
The price is €191
includes taxes & fees
12 Aug - 13 Aug
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (40)
"We stayed here for a night since we had a nearby disc golf tournament. Leah was a great host and the house was super clean and comfy. Quiet neighborhood, cool back porch to hang out. Highly recommend! Thank you Leah!"
The price is €284
includes taxes & fees
13 Aug - 14 Aug
The Watusi Place - A Modern Umpqua Valley Getaway

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

10.0 out of 10, Exceptional, (43)
"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
21 Aug - 22 Aug
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

Charming 3-bedroom cabin on Little River near 8 picturesque water falls

2.0 star property
2.0 out of 10, (1)
"This property is atrocious, people lived in the house until the day before our stay which was booked in early March. The greeting coming in is a sign that says slow the fuck down then a pot plant and trash ,this house is not equipped with anything there was other peoples things in the house and people on the property entering the house while we weren't there, feeding cats on the back patio ,most of the time we were without water,the faucet in the tub was a i in pcv pipe with a nob to turn it off...
Charming 3-bedroom cabin on Little River near 8 picturesque water falls

River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water

9.8 out of 10, Exceptional, (54)
"House has the most amazing views. Perfect location for hiking all of the waterfalls. We would most definitely stay again!"
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water

River Vista Vacation Homes

3.0 star property
9.2 out of 10, Wonderful, (45)
"What a magical place. Just what this busy mom of 3 needed to clear my mind and relax for a couple of days. I wish I could stay longer! I will be back "
River Vista Vacation Homes

Lil Cedar Lodge

The price is €96
includes taxes & fees
13 Aug - 14 Aug
Lil Cedar Lodge

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.4 out of 10, Exceptional, (19)
"Inviting and comfortable "
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

9.8 out of 10, Exceptional, (29)
"This place is a great place to stay. Clean, property manager is great, location is a close drive to anything you need. This was our second time there. Will be back again if we are in the area. "
The price is €287
includes taxes & fees
27 Aug - 28 Aug
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

9.6 out of 10, Exceptional, (20)
"Very clean and we loved how well stocked it was! Thankful for the garage to park in! Easy to find and easy to check in!"
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (34)
"Peaceful and clean."
The price is €161
includes taxes & fees
18 Aug - 19 Aug
A Restful Studio Near a Creek and Forest - Pets

Luxury Riverfront Escape- Hot tub & Fire Pit

9.6 out of 10, Exceptional, (11)
"We fit a lot in during our 4 day stay! A trip to Bandon to enjoy the ocean, wine tasting at Cooper Ridge and Knostman Family Winery, and waterfalls. We enjoyed the fire pit and hot tub each night. The house was nicely decorated and met all of our needs! We walked the neighborhood and spent time at the river. Abby was spot on with her communication. We highly recommend booking a stay at the Monroe River House!"
Luxury Riverfront Escape- Hot tub & Fire Pit

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.4 out of 10, Exceptional, (9)
"great property"
The price is €493
includes taxes & fees
13 Aug - 14 Aug
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Family home

9.6 out of 10, Exceptional, (4)
"I would suggest to everyone to stay here!"
Family home

Bell Sister Flats

2.0 star property
The price is €490
includes taxes & fees
15 Aug - 16 Aug
Bell Sister Flats
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

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 Douglas County Museum of History and Natural History, 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.