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10 Oct - 12 Oct
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31 Oct - 2 Nov
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28 Nov - 30 Nov

Featured Cottages in Winchester and around

Tiny Home w/ RV Hookups
Exterior

Tiny Home w/ RV Hookups

8.6 out of 10, Excellent, (7)
"Very clean highly recommend if you are looking to get away and relax "
The price is €216
includes taxes & fees
19 Oct - 20 Oct
Tiny Home w/ RV Hookups
Snuggle Up in our Teddy Cottage! *New Listing*
Exterior

Snuggle Up in our Teddy Cottage! *New Listing*

10.0 out of 10, Exceptional, (6)
"Property was just as described and photographed. Sometimes that can be disappointing.Loved the attention to detail in the decor and including all essentials.It was very quiet and safe.Would recommend this property to others!"
The price is €137
includes taxes & fees
22 Oct - 23 Oct
Snuggle Up in our Teddy Cottage! *New Listing*
Catch Some ZZZ's at the Grizzly Cottage
Exterior

Catch Some ZZZ's at the Grizzly Cottage

9.6 out of 10, Exceptional, (4)
"Very comfortable and clean, close to hiking trails. We enjoyed our stay very much!"
The price is €164
includes taxes & fees
20 Oct - 21 Oct
Catch Some ZZZ's at the Grizzly Cottage
Story-time Stay at Our Rupert Cottage!
Exterior

Story-time Stay at Our Rupert Cottage!

10.0 out of 10, Exceptional, (2)
"Loved staying here. The staff, the cabin, the atmosphere were perfect for this weary traveler! It was great having the consistentcy of the cabin to stay at while seeking my forevervhome in Nashville! I am so grateful"
The price is €148
includes taxes & fees
7 Oct - 8 Oct
Story-time Stay at Our Rupert Cottage!
Swordfish Suite DOG friendly- Pup Shed Retreat
Exterior

Swordfish Suite DOG friendly- Pup Shed Retreat

10.0 out of 10, Exceptional, (11)
"Very dog and family friendly. Enjoyed our stay. Perfect location!"
The price is €293
includes taxes & fees
27 Oct - 28 Oct
Swordfish Suite DOG friendly- Pup Shed Retreat
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast
Exterior

Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast

10.0 out of 10, Exceptional, (44)
"Beautiful property and wonderful proprietors."
The price is €250
includes taxes & fees
4 Nov - 5 Nov
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast
Peaceful Mountaintop Cottage
Exterior

Peaceful Mountaintop Cottage

9.8 out of 10, Exceptional, (14)
"We had a group in town to see a show at the Caverns. The property had everything we needed and we enjoyed our stay. We will definitely look to stay here next time we are in the area."
The price is €440
includes taxes & fees
6 Oct - 7 Oct
Peaceful Mountaintop Cottage
Bluebird Rest - Lakefront Cottage
Terrace/patio

Bluebird Rest - Lakefront Cottage

10.0 out of 10, Exceptional, (52)
"This was the best hidden gem we have came across. Beautiful house in a perfect location. The host of this property was amazing and very hospitable. They get 10s all across the board. "
The price is €388
includes taxes & fees
14 Oct - 15 Oct
Bluebird Rest - Lakefront Cottage
Smarter than the Average Stay at the Yogi Cottage!
Exterior

Smarter than the Average Stay at the Yogi Cottage!

8.8 out of 10, Excellent, (6)
"We stayed the night to enjoy a concert at the Caverns. The cottage is adorable and the Caverns are amazing. "
Smarter than the Average Stay at the Yogi Cottage!
Visit 100 Aker Woods and Stay at Winnie Cottage!
Exterior

Visit 100 Aker Woods and Stay at Winnie Cottage!

10.0 out of 10, Exceptional, (11)
"Spent the night here while travelking south. The place was perfect for what we needed!"
The price is €137
includes taxes & fees
4 Nov - 5 Nov
Visit 100 Aker Woods and Stay at Winnie Cottage!
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

Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester

10/10 Excellent
"Very clean and had a nice selection of breakfast items. Easy to get to from interstate. "
Janet 1-night trip
Posted 22 hours ago
Microtel Inn & Suites by Wyndham Manchester

Find out more about Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
11,265
Accommodation
62 Cottages
Lowest Price
€55
Highest Price
€237

Frequently asked questions

Why book your cottage in Winchester with Expedia?
Expedia has some excellent cottages in Winchester, so start packing for an unforgettable stay on nature's doorstep. If you have a fixed budget, select how much you're willing to spend and the preferred star rating of your property. Or, use our filters to search for cottages with a kitchen or a pool. We'll help you find the right place whatever your bank balance or plans.
How can I find cheap cottages in Winchester?
An excellent way to find cheap cottages in Winchester is with Expedia's user-friendly filter tool. Narrow your search by budget, star rating and amenities to take advantage of unbeatable rates in just a few keystrokes.
What is there to do in Winchester near my cottage?
The most useful travel accessory is a well-planned itinerary. Tim's Ford Marina is a terrific place to start your exploration of Winchester.

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Explore a world of travel with Expedia