Winchester Vacation Rentals

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Vacation Rentals in Winchester

Singing Waters at N. Umpqua
Stereo
Singing Waters at N. Umpqua
10.0 out of 10, Exceptional, 3 reviews
"The place is clean and neat, but the best part is the backyard with the river running through it. What a gem!"
Singing Waters at N. Umpqua
Heavenly Bungalow, Entire Home!
Exterior
Heavenly Bungalow, Entire Home!
10.0 out of 10, Exceptional, 21 reviews
"This is a great property. It's very convenient for our travels down to visit our kids. Sue pays attention to every detail to make everything very comfortable. Beds and furniture are comfortable and kitchen is very well stocked with all that is needed. It's also located a house away from a nice little park."
Heavenly Bungalow, Entire Home!
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
2 bedrooms, desk, iron/ironing board, travel crib
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
9.8 out of 10, Exceptional, 52 reviews
"We had a lovely stay in this cool, vintage decorated Roseburg house! We were in town for a livestock show for our 13 and 14 year old kiddos were showing sheep. They really loved the record player and the cool games that were provided in the living room. We loved this house because it was very much geared towards family. The decor was really cool and it was very cozy."
The price is ￥20,133
￥34,934 total
includes taxes & fees
Jun 6 - Jun 7
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
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Home Sweet Home
Fridge, microwave, oven, stovetop
Home Sweet Home
5.2 out of 10, 9 reviews
"Full kitchen. Everything was very clean. Mattresses were low quality but everything else was nice. Easy communication with Jimmy"
The price is ￥16,261
￥31,883 total
includes taxes & fees
Jun 11 - Jun 12
Home Sweet Home
Family-Friendly Winston Vacation Rental w/ Deck!
Fridge, microwave, stovetop, dishwasher
Family-Friendly Winston Vacation Rental w/ Deck!
10.0 out of 10, Exceptional, 5 reviews
"The property is very nice with a good view. Very well supplied with all necessary items for cooking and meals. Ease of working with hostess."
Family-Friendly Winston Vacation Rental w/ Deck!
A Restful Studio Near a Creek and Forest - Pets
Property grounds
A Restful Studio Near a Creek and Forest - Pets
10.0 out of 10, Exceptional, 12 reviews
"A small, all-contained unit. It is modern, clean, and quiet. Easy checkin and checkout process. Pleasant, responsive host. It's a beautiful property. A little out of the way but not too far of a drive to town. They don't mind pups and actually make the pups comfortable as well. We'll be back."
The price is ￥18,584
￥30,478 total
includes taxes & fees
Jun 24 - Jun 25
A Restful Studio Near a Creek and Forest - Pets
3 Bedroom House w/Game Room/Pets
Fridge, microwave, oven, stovetop
3 Bedroom House w/Game Room/Pets
9.4 out of 10, Exceptional, 3 reviews
"Stay was nice. House was clean. Well supplied. Neighborhood was ok. Close to where we wanted to go. I would have preferred to text rather than email to contact owner. But she answered quickly. Reasonable price. Would stay here again."
The price is ￥23,231
￥77,501 total
includes taxes & fees
Jun 11 - Jun 12
3 Bedroom House w/Game Room/Pets
The Bucket List Retreat
Property grounds
The Bucket List Retreat
9.6 out of 10, Exceptional, 24 reviews
"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 Bucket List Retreat
Charming Historical lodge across from Umpqua river
Private kitchen
Charming Historical lodge across from Umpqua river
9.4 out of 10, Exceptional, 19 reviews
"A wonderful place to stay highly recommended, and will go there again when we visit Glide."
The price is ￥23,231
￥26,881 total
includes taxes & fees
Jun 6 - Jun 7
Charming Historical lodge across from Umpqua river
The Watusi Place - A Modern Umpqua Valley Getaway
Terrace/patio
The Watusi Place - A Modern Umpqua Valley Getaway
10.0 out of 10, Exceptional, 30 reviews
"We stayed here just one night so we could go to the wildlife safari in the late afternoon. Convenient location. Beautiful well stocked house. Immaculately clean Wildlife Safari was great and very reasonably priced"
The price is ￥30,200
￥66,038 total
includes taxes & fees
Jul 2 - Jul 3
The Watusi Place - A Modern Umpqua Valley Getaway
Historic Lodge across the street from the Umpqua River
Private kitchen
Historic Lodge across the street from the Umpqua River
9.8 out of 10, Exceptional, 18 reviews
"The lodge owner JoAnne came to meet us as we pulled up in our truck. She gave a quick tour of the facility and our room. Very welcoming of our small dog, Bill. Invited us to a potluck on site that evening. There was an awesome musical trio of JoAnne’s friends. They played folk and rock tunes from the 60’s, 70’s and 80’s until about 9 pm. Very cool! Room and our restroom very clean. Bed very comfy. Best of all a fresh loaf of banana bread awaited us in our room. Very cool!"
The price is ￥19,359
￥22,794 total
includes taxes & fees
Jun 6 - Jun 7
Historic Lodge across the street from the Umpqua River
Firewater Lodge Cabin Experience
Terrace/patio
Firewater Lodge Cabin Experience
10.0 out of 10, Exceptional, 34 reviews
"When we saw the description of this magical place we had to spend some time here. We stay in several VRBO properties every year. This ranks among the best all around. Every detail was covered. The kitchen is well equipped (quality cookware) and stocked. It is secluded, but that is what we wanted. We felt safe and the house is secure. It is a huge well manicured property with great indoor and outdoor spaces. Our dog was in heaven exploring every nook including the beautiful stream babbling...
Firewater Lodge Cabin Experience
Lost World Lodge - Your Jurassic Park Vacation Rental
TV, foosball, stereo
Lost World Lodge - Your Jurassic Park Vacation Rental
9.0 out of 10, Wonderful, 2 reviews
"Loved the Lost World theme of the apartment. It was super clean, spacious, and great location. The KOA park is the cleanest park I've seen and we love the drive in movie theater."
Lost World Lodge - Your Jurassic Park Vacation Rental
Sophisticated Bungalow, Sparkling clean!
Fridge, microwave, oven, stovetop
Sophisticated Bungalow, Sparkling clean!
10.0 out of 10, Exceptional, 49 reviews
"Went to visit our daughter. House was just a few blocks from where she lives. She came for bfast each morning and I was even able to cook a nice dinner for her and her friends! Kitchen is well stocked and lots of room for hanging out and playing games! Will definitely stay again!"
Sophisticated Bungalow, Sparkling clean!
Quiet and Comfy (Zip Tye Ranch)
TV
Quiet and Comfy (Zip Tye Ranch)
9.0 out of 10, Wonderful, 23 reviews
"Nice house and very quiet area"
Quiet and Comfy (Zip Tye Ranch)
Charming Private Cottage in Southern Oregon Close to I-5 & NO surprise fees
Exterior
Charming Private Cottage in Southern Oregon Close to I-5 & NO surprise fees
10.0 out of 10, Exceptional, 27 reviews
"If you’re looking for a calm quiet stay, this is it."
The price is ￥28,186
￥32,539 total
includes taxes & fees
Jun 13 - Jun 14
Charming Private Cottage in Southern Oregon Close to I-5 & NO surprise fees
Indigo Collective - Modern Home
Private kitchen
Indigo Collective - Modern Home
10.0 out of 10, Exceptional, 2 reviews
"We loved staying here! Beautifully decorated and very comfortable! Beds were super comfortable - although 1 in the double queen room is very, very soft. Kitchen is well appointed - plenty of pans and cooking ware. Bathrooms were stocked - included shampoos, conditioner and soaps. As well as tons of towels, which was appreciated! Hot water is very hot, which was great but be warned if you have littles - could be too much for them. Will absolutely stay here again! Lovely!"
Indigo Collective - Modern Home
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Property grounds
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
9.8 out of 10, Exceptional, 16 reviews
"Nice"
The price is ￥19,359
￥35,953 total
includes taxes & fees
Jun 16 - Jun 17
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg
Fridge, microwave, oven, stovetop
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg
9.6 out of 10, Exceptional, 10 reviews
"Amazing stay. Great location. Very peaceful and a beautiful house! We enjoyed every part of it."
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg
Xenia House-Roseburg Retreat with a View!
Terrace/patio
Xenia House-Roseburg Retreat with a View!
10.0 out of 10, Exceptional, 5 reviews
"Lovely house and great host. Would happily stay again!"
Xenia House-Roseburg Retreat with a View!
Don't see what you're looking for?
See all available properties in Winchester
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.

Other types of properties in Winchester you may be interested in

Singing Waters at N. Umpqua
Stereo
Singing Waters at N. Umpqua
10.0 out of 10, Exceptional, 3 reviews
"The place is clean and neat, but the best part is the backyard with the river running through it. What a gem!"
Singing Waters at N. Umpqua
Riverfront Inn Roseburg
BBQ/picnic area
Riverfront Inn Roseburg
2.0 star property
8.6 out of 10, Excellent, 1,104 reviews
"The view from the balcony was so pretty and relaxing. "
The price is ￥18,120
￥19,842 total
includes taxes & fees
Jun 6 - Jun 7
Riverfront Inn Roseburg
Super 8 by Wyndham Roseburg
Exterior
Super 8 by Wyndham Roseburg
2.5 star property
7.8 out of 10, Good, 1,006 reviews
"Front desk was terrific "
The price is ￥12,376
￥13,553 total
includes taxes & fees
Jun 16 - Jun 17
Super 8 by Wyndham 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.

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 vacation rental in Winchester?

Yes, we offer vacation rentals near well known sights in Winchester, or you can choose a more secluded option if you want a relaxing place to stay. Winchester is known for its restaurants.

What are some of the best vacation rentals that Winchester has to offer?

Whistlers River House - Spring Special: This vacation home rental near Winchester is located on a river and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

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 larger area.

What’s a vacation rental in Winchester like?

Vacation rentals are privately owned properties you can book for several days or longer in Winchester. Vacation rentals feature extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family getaway.

Recent reviews of Winchester properties
Expedia verified reviews

Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR

5/5 Excellent
"The sheets had pilled balls all over it and a hair tangled between them. The place was immaculate but where I put my body was gross!"
A verified traveler stayed at Motel 6 Sutherlin, OR
Posted 20 hours ago
Motel 6 Sutherlin, OR