Winchester Vacation Rentals

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Jul 26 - Jul 27
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Vacation Rentals in Winchester

Singing Waters at N. Umpqua
Interior

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
Interior

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

9.8 out of 10, Exceptional, (80)
"Love this little abode and recommend "
The price is ￥18,461
￥32,022 total
includes taxes & fees
Jul 31 - Aug 1
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Tiny House nestled into the Forest on 160 acre Playground.
Exterior

Tiny House nestled into the Forest on 160 acre Playground.

9.4 out of 10, Exceptional, (9)
"Stayed here for one evening while touring wineries in the region. Fantastic location, great communication from hosts, and a delightful property. Would recommend! "
The price is ￥17,014
￥23,266 total
includes taxes & fees
Jul 28 - Jul 29
Tiny House nestled into the Forest on 160 acre Playground.
A Restful Studio Near a Creek and Forest - Pets
Terrace/patio

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (33)
"Peaceful and clean."
The price is ￥16,246
￥26,928 total
includes taxes & fees
Jul 30 - Jul 31
A Restful Studio Near a Creek and Forest - Pets
Firewater Lodge Cabin Experience
Outdoor dining

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (60)
"The property is beautiful. "
Firewater Lodge Cabin Experience
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Property grounds

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (27)
"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 ￥16,984
￥32,345 total
includes taxes & fees
Aug 4 - Aug 5
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Fridge, microwave, oven, stovetop

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.8 out of 10, Exceptional, (7)
"The house was overall good nice clean area was nice. unfortunately the hot tub and the pool were not working when we got and did not work for our entire stay there. but overall nice place"
The price is ￥46,921
￥83,752 total
includes taxes & fees
Jul 30 - Jul 31
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
The Watusi Place - A Modern Umpqua Valley Getaway
Outdoor dining

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (39)
"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 ￥19,539
￥51,486 total
includes taxes & fees
Jul 30 - Jul 31
The Watusi Place - A Modern Umpqua Valley Getaway
Charming 3-bedroom cabin on Little River near 8 picturesque water falls
Property grounds

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

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 ￥21,390
￥48,813 total
includes taxes & fees
Aug 15 - Aug 16
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Lil Cedar Lodge
1 bedroom, bed sheets

Lil Cedar Lodge

The price is ￥12,627
￥16,564 total
includes taxes & fees
Jul 28 - Jul 29
Lil Cedar Lodge
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Outdoor dining

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
Bell Sister Flats
Deluxe Apartment, City View | Private kitchen

Bell Sister Flats

2.0 star property
The price is ￥49,772
￥76,159 total
includes taxes & fees
Aug 27 - Aug 28
Bell Sister Flats
Family-Friendly Winston Vacation Rental w/ Deck!
Fridge, microwave, stovetop, dishwasher

Family-Friendly Winston Vacation Rental w/ Deck!

10.0 out of 10, Exceptional, (18)
"Very nice place. They have thought of everything. Thanks "
Family-Friendly Winston Vacation Rental w/ Deck!
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Interior

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.6 out of 10, Exceptional, (17)
"Inviting and comfortable "
The price is ￥13,144
￥25,714 total
includes taxes & fees
Jul 28 - Jul 29
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Family home
Fridge, microwave, oven, stovetop

Family home

9.6 out of 10, Exceptional, (4)
"I would suggest to everyone to stay here!"
Family home
Southern Oregon Cabin: Fire Pit & Private Pond!
House (1 Bedroom) | Interior

Southern Oregon Cabin: Fire Pit & Private Pond!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Cute little place! Especially liked the patio and outside areas. Inside needs a few finishing touches like coat hooks on back of doors, but place is very new, clean and worked great for our few days there."
Southern Oregon Cabin: Fire Pit & Private Pond!
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, (7)
"Great property with great amenities! I would recommend this location to anyone."
Lost World Lodge - Your Jurassic Park Vacation Rental
River Vista Vacation Homes
Property entrance

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
Romantic Vineyard Getaway in Oakland: Mtn Views!
House (1 Bedroom) | Interior

Romantic Vineyard Getaway in Oakland: Mtn Views!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Property was well organized with all the necessities/amenities that made our stay that much more comfortable. Perhaps instructions on how to operate front door lock would be helpful. Otherwise, everything else was perfect. Thank you! "
Romantic Vineyard Getaway in Oakland: Mtn Views!
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

Motel 6 Sutherlin, OR

Motel 6 Sutherlin, OR

10/10 Excellent
"Nice for the price"
Mitch 1-night trip
Posted 1 day ago
Motel 6 Sutherlin, OR

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?


~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath: This vacation home rental near Winchester offers a selection of games, a barbecue grill, 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 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.