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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 47 Vacation Homes in Winchester with updated reviews, rates, and availability.

River Vista Vacation Homes
Property grounds

River Vista Vacation Homes

3.0 star property
9.0 out of 10, Wonderful, (44)
"I loved the wild river right out the door"
River Vista Vacation Homes
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, (26)
"Search a beautiful, quiet and serene place to stay. We were so mesmerized by the view that we didn't even turn on the TV Such a sweet escape, even just for the weekend. We will definitely be back!"
The price is AED 349
AED 607 total
includes taxes & fees
25 Mar - 26 Mar
A Restful Studio Near a Creek and Forest - Pets
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
Fridge, microwave, oven, stovetop

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

9.6 out of 10, Exceptional, (55)
"We had a wonderful stay. With the number of bedrooms and bathrooms, it was perfect for our group size. The host was great and very responsive when needed. The game room provided a fun time for every one of all ages. With the folding tables and chairs located on site, it provided the perfect amount of seating for our group for our Thanksgiving meal. Would definitely recommend this place and hope to rent it again in the future."
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
The Watusi Place - A Modern Umpqua Valley Getaway
Outdoor dining

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 AED 474
AED 1,247 total
includes taxes & fees
23 Mar - 24 Mar
The Watusi Place - A Modern Umpqua Valley Getaway
Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (7)
"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...
Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Outdoor dining

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

10.0 out of 10, Exceptional, (10)
"We have stayed at this house on previous trips to the Roseburg area. It is always a relaxing stay at this house. The rooms are clean and the house is located near our daughter and her family."
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
River Vista Homes: Enjoy Swimming, Fishing, and Relaxation in Nature's Beauty
Miscellaneous

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 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, (24)
"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 Urban Boho Charmer with Private Backyard, BBQ & Hammock
Cozy Roseburg Home w/ Fire Pit + Gas Grill!
Hair dryer, towels

Cozy Roseburg Home w/ Fire Pit + Gas Grill!

9.8 out of 10, Exceptional, (11)
"12 day stay small would be good for couple gŕeat appliances ken who lives next door was easy to get along with had things all ready to go when i arrived "
Cozy Roseburg Home w/ Fire Pit + Gas Grill!
The Farmhouse on the North Umpqua River
Bar (on property)

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
Tiny House nestled into the Forest on 160 acre Playground.
Property grounds

Tiny House nestled into the Forest on 160 acre Playground.

8.6 out of 10, Excellent, (4)
"Cute tiny house on an absolutely lovely, serene forested hillside. Really close to town, all things considered - about 20 minutes from the hospital where I was working for the month! The one downside that is only an issue with more extended stays like mine - the compost toilet did get a tad smelly as the weeks went by. Not to an unbearable degree but just a small caveat to the five stars! "
The price is AED 470
AED 626 total
includes taxes & fees
23 Mar - 24 Mar
Tiny House nestled into the Forest on 160 acre Playground.
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
2 bedrooms, desk, iron/ironing board, free WiFi

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

9.8 out of 10, Exceptional, (71)
"Love this little abode and recommend "
The price is AED 459
AED 784 total
includes taxes & fees
7 Apr - 8 Apr
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Indigo Collective - Modern Home
Private kitchen

Indigo Collective - Modern Home

10.0 out of 10, Exceptional, (15)
"The home was clean, comfortable, and everything worked well!A perfect place to stay for your visit to Roseburg, OR!"
The price is AED 912
AED 1,927 total
includes taxes & fees
22 Apr - 23 Apr
Indigo Collective - Modern Home
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, (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 AED 397
AED 1,014 total
includes taxes & fees
30 Mar - 31 Mar
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Family-Friendly Winston Vacation Rental w/ Deck!
Fridge, microwave, stovetop, dishwasher

Family-Friendly Winston Vacation Rental w/ Deck!

10.0 out of 10, Exceptional, (11)
"We found out that my Father was dying. We booked this Abnb close to my dad's house. "
Family-Friendly Winston Vacation Rental w/ Deck!
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Exterior

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

10.0 out of 10, Exceptional, (10)
"Very comfortable "
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Property grounds

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

9.6 out of 10, Exceptional, (29)
"This place is worth your money! The beds and bedding are very comfortable. The shower pressure is great. The amenities excel. Very quiet neighborhood. Communication with host is excellent. I will recommend this place to my friends and family. Would stay here again for sure."
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Terrace/patio

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

10.0 out of 10, Exceptional, (21)
"Excellent experience! We were passing through and wanted a cozy experience from multiple hotel stays. Our hosts were outstanding and so friendly, attentive to every little detail to make us feel welcomed and comfortable. An outstanding bed and breakfast experience!"
The price is AED 661
AED 812 total
includes taxes & fees
24 Mar - 25 Mar
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water
Miscellaneous

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

9.8 out of 10, Exceptional, (52)
"*"
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water
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

9.8 out of 10, Exceptional, (23)
"Perfect "
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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Other property types in Winchester

Singing Waters at N. Umpqua
Interior

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
Firewater Lodge Cabin Experience
Outdoor dining

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (53)
"Had a wonderful time and wished we could stay longer."
Firewater Lodge Cabin Experience
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, (26)
"Search a beautiful, quiet and serene place to stay. We were so mesmerized by the view that we didn't even turn on the TV Such a sweet escape, even just for the weekend. We will definitely be back!"
The price is AED 349
AED 607 total
includes taxes & fees
25 Mar - 26 Mar
A Restful Studio Near a Creek and Forest - Pets
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.