Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Singing Waters at N. Umpqua

10.0 out of 10, Exceptional, (5)
"Beautifully decorated house! Loved the view of the river in the backyard. So clean and new! No complaints!!"
Singing Waters at N. Umpqua

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

9.8 out of 10, Exceptional, (23)
"Gary was amazing, the house was super clean and well stocked. I was on a work trip so i was only there in the evenings, but it was perfect! Id love to ce back!"
The price is €294
includes taxes & fees
1 Dec - 2 Dec
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

The Bucket List Retreat

9.6 out of 10, Exceptional, (24)
"Comfy beds, great location to our activity, accommodating owner who went out of their way to send us something we left behind. Would definitely stay a this property again."
The price is €463
includes taxes & fees
25 Nov - 26 Nov
The Bucket List Retreat

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

9.6 out of 10, Exceptional, (67)
"The house is a 1950's home that has been decorated throughout in a 50's/60's style, right down to the record player and albums. We loved our stay, and would gladly go back, and the kids enjoyed groovin' to the beach boys "
The price is €221
includes taxes & fees
26 Nov - 27 Nov
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (19)
"Host is very accommodating and thoughtful. It's a beautiful property. No complaints at all. "
The price is €157
includes taxes & fees
25 Nov - 26 Nov
A Restful Studio Near a Creek and Forest - Pets

Sophisticated Bungalow, Sparkling clean!

10.0 out of 10, Exceptional, (60)
"Location is walkable to restaurants and pubs. 4 adults on a wine tasting weekend. The kitchen was well-stocked, comfortable beds, and a great space to just hang out and chat with each other. Highly recommend. "
Sophisticated Bungalow, Sparkling clean!

Heavenly Bungalow, Entire Home!

10.0 out of 10, Exceptional, (32)
"This place was perfect for our weekend stay. The place is actually a little bigger than the pictures make it look, it was cozy and fully stocked with everything we needed for the weekend. "
Heavenly Bungalow, Entire Home!

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (45)
"We loved everything about our stay here!! Wonderful communication with our host, clean, and quiet were some of our first impressions! Check-in and checkout were simple and everything I could have thought of as a question is answered for me before I think of it. Open and comfortable living area made for a great movie night. We enjoyed playing in the creek and sitting by the fire pit! The kitchen was fully stocked, so appreciated! The beds provided plenty of space for all of us and everyone...
Firewater Lodge Cabin Experience

River Vista Homes: Enjoy Swimming, Fishing, and Relaxation in Nature's Beauty

10.0 out of 10, Exceptional, (12)
"This is the second time staying at this property and it is so peaceful. It's right on the river and is close to many trails and waterfalls. I highly recommend!"
River Vista Homes: Enjoy Swimming, Fishing, and Relaxation in Nature's Beauty

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (34)
"We had a great stay and home was just what was advertised. There were so many personal touches and the owner was great to deal with. There was a problem with the A/C before we arrived which was quickly relayed to us by owner and they had it fixed just after our arrival. We will definitely be back next time we are in town. "
The price is €419
includes taxes & fees
5 Dec - 6 Dec
The Watusi Place - A Modern Umpqua Valley Getaway

Indigo Collective - Modern Home

10.0 out of 10, Exceptional, (8)
"Thx"
The price is €487
includes taxes & fees
5 Dec - 6 Dec
Indigo Collective - Modern Home

Cozy Roseburg Home w/ Fire Pit + Gas Grill!

9.6 out of 10, Exceptional, (10)
"This place was heaven. VERY clean, decorated adorably and well supplied for all my needs. It is in a quiet neighborhood and provided me a respite in the evenings after a stressful day. The patio and plants outside were beautiful. I just can’t find enough words to say how great this VRBO is. I hope to come back!"
Cozy Roseburg Home w/ Fire Pit + Gas Grill!

Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg

9.8 out of 10, Exceptional, (19)
"Convenient location, large (heavily chlorinated) spa and lots of space to spread out or hang out together. Great outdoor space for meals. "
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.6 out of 10, Exceptional, (11)
"Loved the location, easy to DoorDash food(I’m lazy, it’s vacation) Cozy space, comfy bed. Ease of use in all aspects of the house. Nice central location for our random travels to crater lake and the wildlife safari 👏"
The price is €171
includes taxes & fees
24 Nov - 25 Nov
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Charming Historic lodge #2

9.6 out of 10, Exceptional, (12)
"Great spot to stay for close access to fishing and other mountain sports. I noticed many white water rafters. The property is also close to Roseburg and the many wineries in the valley. Very clean and owner great people. Have a nice bar on property and there was small band playing Friday night."
The price is €121
includes taxes & fees
24 Nov - 25 Nov
Charming Historic lodge #2

Xenia House-Roseburg Retreat with a View!

10.0 out of 10, Exceptional, (8)
"We loved the location and layout of the lovely home. It had everything we needed and a great view. We hope the host will forgive for forgetting to start the dishwasherwith a few dishes"
Xenia House-Roseburg Retreat with a View!

Tiny House nestled into the Forest on 160 acre Playground.

8.8 out of 10, Excellent, (3)
"We had an amazing time here it was so quite and peaceful and the host were amazing we will be going back"
The price is €167
includes taxes & fees
24 Dec - 25 Dec
Tiny House nestled into the Forest on 160 acre Playground.

The Farmhouse on the North Umpqua River

9.0 out of 10, Wonderful, (6)
"Usually staying near or in the mountains nets you with a long drive to go get anything let the bar combined with the deli across the street makes it really easy to stock up on food or just get general necessities without having to hop in your car."
The Farmhouse on the North Umpqua River

Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.

10.0 out of 10, Exceptional, (6)
"The Monroe River House in Roseburg, OR was the perfect home for us. The master bedroom was spacious, and the bed was super comfortable. Having an additional BR and bathroom was a bonus, too. The house and kitchen were well-stocked and had everything we needed and more - like plastic bags to keep food in, etc. The yard was huge, and we spent a few afternoons hanging out at the little beach on the river at the bottom of the property. The area is beautiful with lots of local wineries nearby. We...
The price is €494
includes taxes & fees
4 Dec - 5 Dec
Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.

Just off I-5, RV available on secluded lot. 2 livestock stalls. Close to town.

10.0 out of 10, Exceptional, (3)
"Stayed here while figuring out my living situation during the sale of my place. Doug was so helpful and kind. I love the setting, watching cows graze while drinking coffee in the morning. Bed is comfortable. Very quiet. If you like a little solitude while RV'ing, you should enjoy it here."
Just off I-5, RV available on secluded lot. 2 livestock stalls. Close to town.
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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Other types of properties in Winchester you may be interested in

Singing Waters at N. Umpqua

10.0 out of 10, Exceptional, (5)
"Beautifully decorated house! Loved the view of the river in the backyard. So clean and new! No complaints!!"
Singing Waters at N. Umpqua

Riverfront Inn Roseburg

2.0 star property
8.6 out of 10, Excellent, (1230)
"Stayed here many times, great cozy hotel on the river. "
The price is €103
includes taxes & fees
1 Dec - 2 Dec
Riverfront Inn Roseburg

Best Western Garden Villa Inn

2.5 star property
8.0 out of 10, Very good, (1035)
"Great front desk staff on every shift. Very helpful and friendly. "
The price is €89
includes taxes & fees
1 Dec - 2 Dec
Best Western Garden Villa Inn
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.

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?

The Bucket List Retreat: 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 4 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.