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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 49 Vacation Homes in Winchester with updated reviews, rates, and availability.

The Watusi Place - A Modern Umpqua Valley Getaway
Outdoor dining

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (36)
"Everything was great‼️"
The price is AED 386
AED 1,140 total
includes taxes & fees
8 May - 9 May
The Watusi Place - A Modern Umpqua Valley Getaway
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Interior

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.0 out of 10, Wonderful, (2)
"The house was clean, and nicely furnished. The property was easy to find and the check instructions were accurate and easy. The host communication was extremely prompt. We would stay again."
The price is AED 1,194
AED 2,103 total
includes taxes & fees
8 May - 9 May
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
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, (31)
"Great place, comfortable and clean. The host was very polite."
The price is AED 349
AED 607 total
includes taxes & fees
8 May - 9 May
A Restful Studio Near a Creek and Forest - Pets
<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, (73)
"Love this little abode and recommend "
The price is AED 459
AED 788 total
includes taxes & fees
12 May - 13 May
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Luxury Riverfront Escape- Hot tub & Fire Pit
Fridge, microwave, oven, stovetop

Luxury Riverfront Escape- Hot tub & Fire Pit

9.4 out of 10, Exceptional, (9)
"We stayed for a family wedding and it was a great house. Comfortable, clean and the patio and river access were great! I would recommend and stay again!"
Luxury Riverfront Escape- Hot tub & Fire Pit
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
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, (56)
"Our stay was wonderful. The house was clean and had everything we needed for our stay. Great spot for a large group!!"
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
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, (16)
"Lovely house and great host. Would happily stay again!"
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Indigo Collective - Modern Comfort & Bold Design
Private kitchen

Indigo Collective - Modern Comfort & Bold Design

10.0 out of 10, Exceptional, (17)
"We were only at this house for one quick night stay, but found it very comfortable. "
The price is AED 880
AED 1,869 total
includes taxes & fees
4 Jun - 5 Jun
Indigo Collective - Modern Comfort & Bold Design
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
Stylish Escape - Chic & Cozy with relaxing backyard
Property grounds

Stylish Escape - Chic & Cozy with relaxing backyard

10.0 out of 10, Exceptional, (1)
"A great place to stay in a developed neighborhood. Home had good decor with a layout for cost effectiveness."
The price is AED 865
AED 1,888 total
includes taxes & fees
14 May - 15 May
Stylish Escape - Chic & Cozy with relaxing backyard
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Interior

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.6 out of 10, Exceptional, (12)
"Inviting and comfortable "
The price is AED 327
AED 640 total
includes taxes & fees
9 May - 10 May
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Cozy Roseburg Home w/ Fire Pit + Gas Grill!
Hair dryer, towels

Cozy Roseburg Home w/ Fire Pit + Gas Grill!

9.6 out of 10, Exceptional, (10)
"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.

8.8 out of 10, Excellent, (5)
"We had an amazing time here it was so quite and peaceful and the host were amazing we will be going back"
The price is AED 470
AED 630 total
includes taxes & fees
9 May - 10 May
Tiny House nestled into the Forest on 160 acre Playground.
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, (24)
"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 389
AED 1,017 total
includes taxes & fees
13 May - 14 May
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, (13)
"The house was immaculate. Communication with the property manager was terrific. We had an excellent time for the two nights we stayed. "
Family-Friendly Winston Vacation Rental w/ Deck!
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 909
AED 1,116 total
includes taxes & fees
8 May - 9 May
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)
"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
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
Exterior

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 AED 327
AED 640 total
includes taxes & fees
8 May - 9 May
Red Tiny Twins, Downtown Eco & Pet Friendly Stay
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)
"Extremely relaxing. Beautifully done house on the North Umpqua River. Just lovely. Look forward to future stays!"
Singing Waters at N. Umpqua
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Interior

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.6 out of 10, Exceptional, (12)
"Inviting and comfortable "
The price is AED 327
AED 640 total
includes taxes & fees
9 May - 10 May
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
Firewater Lodge Cabin Experience
Outdoor dining

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (55)
"We are repeat renters and thoroughly enjoy our home away from home every year. Thank you!"
Firewater Lodge Cabin Experience
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.