Holiday Homes in Winchester

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Featured Holiday Homes in Winchester and around

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

9.8 out of 10, Exceptional, (82)
"April answered all my emails immediately and was very nice. Loved the location."
The price is €190
includes taxes & fees
31 Aug - 1 Sept
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

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

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (28)
"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 €191
includes taxes & fees
18 Aug - 19 Aug
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

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

10.0 out of 10, Exceptional, (43)
"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 €180
includes taxes & fees
1 Sept - 2 Sept
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (41)
"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 €342
includes taxes & fees
19 Aug - 20 Aug
The Watusi Place - A Modern Umpqua Valley Getaway

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

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

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

9.8 out of 10, Exceptional, (29)
"House worked great. Convenient location. Clean and comfortable. Will stay again next"
The price is €276
includes taxes & fees
24 Aug - 25 Aug
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

Family home

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

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 €138
includes taxes & fees
17 Aug - 18 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)
"Inviting and comfortable "
The price is €148
includes taxes & fees
14 Sept - 15 Sept
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

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

Luxury Riverfront Escape- Hot tub & Fire Pit

9.6 out of 10, Exceptional, (11)
"We fit a lot in during our 4 day stay! A trip to Bandon to enjoy the ocean, wine tasting at Cooper Ridge and Knostman Family Winery, and waterfalls. We enjoyed the fire pit and hot tub each night. The house was nicely decorated and met all of our needs! We walked the neighborhood and spent time at the river. Abby was spot on with her communication. We highly recommend booking a stay at the Monroe River House!"
Luxury Riverfront Escape- Hot tub & Fire Pit

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 €153
includes taxes & fees
18 Aug - 19 Aug
Red Tiny Twins, Downtown Eco & Pet Friendly Stay

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (34)
"Peaceful and clean."
The price is €159
includes taxes & fees
27 Aug - 28 Aug
A Restful Studio Near a Creek and Forest - Pets

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.4 out of 10, Exceptional, (9)
"great property"
The price is €469
includes taxes & fees
27 Aug - 28 Aug
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Stylish Escape - Chic & Cozy with relaxing backyard

10.0 out of 10, Exceptional, (4)
"Great place to stay. Was clean and updated older house, with a big back yard. Perfect for my wife, three kids, three granddaughters, and I."
Stylish Escape - Chic & Cozy with relaxing backyard

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

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

9.6 out of 10, Exceptional, (58)
"This was amazing stay. Great location, close to every place we wanted to go. It was very nice and clean. We will definitely be staying again. "
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Fisherman’s paradise in wine country. www.umpquariverlodge.com

Fisherman’s paradise in wine country. www.umpquariverlodge.com
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