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Top 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

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (44)
"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 £296
includes taxes & fees
7 Sept - 8 Sept
The Watusi Place - A Modern Umpqua Valley Getaway

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

9.8 out of 10, Exceptional, (45)
"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 £156
includes taxes & fees
1 Sept - 2 Sept
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

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 £120
includes taxes & fees
28 Aug - 29 Aug
Tiny House nestled into the Forest on 160 acre Playground.

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.4 out of 10, Exceptional, (19)
"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."
The price is £128
includes taxes & fees
14 Sept - 15 Sept
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

9.8 out of 10, Exceptional, (12)
"Enjoyed the accommodations. just as advertised would stay again."
The price is £132
includes taxes & fees
7 Sept - 8 Sept
Red Tiny Twins, Downtown Eco & Pet Friendly Stay

Lil Cedar Lodge

The price is £86
includes taxes & fees
30 Aug - 31 Aug
Lil Cedar Lodge

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

River Vista Vacation Homes

3.0 star property
9.2 out of 10, Wonderful, (45)
"The place was right on the river which was beautiful and it had everything that we would need. It was clean and pretty roomy for my family and I to spend the weekend there and we absolutely loved it! We’re already trying to make another trip out here!"
River Vista Vacation Homes

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

9.6 out of 10, Exceptional, (15)
"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 Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (30)
"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 £163
includes taxes & fees
5 Sept - 6 Sept
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

Family home

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

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

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

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (34)
"Very nice property. "
The price is £129
includes taxes & fees
4 Sept - 5 Sept
A Restful Studio Near a Creek and Forest - Pets

Just off I-5, RV available on a secluded lot. Close to town.

9.8 out of 10, Exceptional, (7)
"Great place to stay, especially if you have horses. Owner was quick to respond if I had any questions or problems. I would recommend this place for couples, friends, or small families."
Just off I-5, RV available on a secluded lot. Close to town.

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.4 out of 10, Exceptional, (9)
"great property"
The price is £406
includes taxes & fees
28 Aug - 29 Aug
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Bell Sister Flats

2.0 star property
The price is £318
includes taxes & fees
31 Aug - 1 Sept
Bell Sister Flats

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

9.6 out of 10, Exceptional, (21)
"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

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

9.8 out of 10, Exceptional, (28)
"We had a great time! The hosts were very fast in responding to any questions we had and the house was clean, comfortable and had all the amenities to make it a great family trip!"
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of 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.
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Top Winchester Hotel Reviews

Find out more about Winchester

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as £86 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 Watusi Place - A Modern Umpqua Valley Getaway: This holiday home rental outside of Winchester is located in a rural location, and has a fireplace, a patio 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.