Search Cottages in Winchester

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Cottages in Winchester

The Blue Heron - Lake Side Chalet
Property grounds

The Blue Heron - Lake Side Chalet

10.0 out of 10, Exceptional, (96)
"This place was amazing.If you enjoy just relaxing and watching the world go by this is the place to do it."
The Blue Heron - Lake Side Chalet
Holiday Cottage at Tim's Ford Lake next to Marina and Restaurant
Outdoor dining

Holiday Cottage at Tim's Ford Lake next to Marina and Restaurant

10.0 out of 10, Exceptional, (35)
"We absolutely enjoyed our stay. We loved being able to ride the golf cart and fish. We were close to several areas and great restaurants! We would definitely stay here again. "
Holiday Cottage at Tim's Ford Lake next to Marina and Restaurant
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 AED 236
AED 573 total
includes taxes & fees
20 Oct - 21 Oct
Snuggle Up in our Teddy Cottage! *New Listing*
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 AED 826
AED 1,637 total
includes taxes & fees
30 Sep - 1 Oct
Bluebird Rest - Lakefront 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 AED 236
AED 622 total
includes taxes & fees
1 Oct - 2 Oct
Story-time Stay at Our Rupert Cottage!
“License To Chill”. Lake Cottage at Tims Ford Lake Golf cart/Fire pit/Marina
Property grounds

“License To Chill”. Lake Cottage at Tims Ford Lake Golf cart/Fire pit/Marina

10.0 out of 10, Exceptional, (15)
"Great view, quiet and secluded deck, great floor plan."
“License To Chill”. Lake Cottage at Tims Ford Lake Golf cart/Fire pit/Marina
Lake it Oar Leave it- Lake front Tim's Ford Lake with DOCK
Property grounds

Lake it Oar Leave it- Lake front Tim's Ford Lake with DOCK

9.8 out of 10, Exceptional, (28)
"Clean, and accurate listing. "
Lake it Oar Leave it- Lake front Tim's Ford Lake with DOCK
Historic 1940's Cottage Near Tim's Ford Lake & Town Square Fully Remodeled
Exterior

Historic 1940's Cottage Near Tim's Ford Lake & Town Square Fully Remodeled

2.0 star property
10.0 out of 10, Exceptional, (5)
"Used for work housing "
Historic 1940's Cottage Near Tim's Ford Lake & Town Square Fully Remodeled
Tiny Home w/ RV Hookups
Exterior

Tiny Home w/ RV Hookups

8.6 out of 10, Excellent, (7)
"Perfect little spot, nice tiny home. Would stay again."
The price is AED 493
AED 902 total
includes taxes & fees
2 Oct - 3 Oct
Tiny Home w/ RV Hookups
Cozy family friendly 2 bedroom lakefront cottage in charming Tracy City TN
Outdoor dining

Cozy family friendly 2 bedroom lakefront cottage in charming Tracy City TN

Cozy family friendly 2 bedroom lakefront cottage in charming Tracy City TN
The Livery at Rainbows End
Outdoor dining

The Livery at Rainbows End

10.0 out of 10, Exceptional, (4)
"This was a great little bungalow. "
The Livery at Rainbows End
Charming cottage in wooded location
Terrace/patio

Charming cottage in wooded location

10.0 out of 10, Exceptional, (31)
"We've stayed in this adorable cottage several times and it is always a pleasure. Close to Sewanee campus, while also being cozily secluded. "
Charming cottage in wooded location
Hollerback Hunt & Yacht Club, peaceful lakefront with private dock on 6 Acres
Exterior

Hollerback Hunt & Yacht Club, peaceful lakefront with private dock on 6 Acres

9.6 out of 10, Exceptional, (130)
"Everything was great! The house, the swimming, the bonfires, the view . . . We couldn't have asked for a nicer long weekend. "
Hollerback Hunt & Yacht Club, peaceful lakefront with private dock on 6 Acres
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 AED 236
AED 692 total
includes taxes & fees
1 Oct - 2 Oct
Catch Some ZZZ's at the Grizzly 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 AED 236
AED 573 total
includes taxes & fees
1 Oct - 2 Oct
Visit 100 Aker Woods and Stay at Winnie Cottage!
Lakeside Cottage Retreat at Tim's Ford Lake
Property grounds

Lakeside Cottage Retreat at Tim's Ford Lake

10.0 out of 10, Exceptional, (35)
"We came in for the weekend. The location was walking distance from a restaurant in the lake. It was great! "
Lakeside Cottage Retreat at Tim's Ford Lake
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. "
The price is AED 236
AED 573 total
includes taxes & fees
1 Oct - 2 Oct
Smarter than the Average Stay at the Yogi 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 AED 400
AED 1,256 total
includes taxes & fees
30 Sep - 1 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 AED 643
AED 1,053 total
includes taxes & fees
1 Oct - 2 Oct
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast
On-site Trails + Furnished Deck: Monteagle Escape!
House (1 Bedroom) | Interior

On-site Trails + Furnished Deck: Monteagle Escape!

3.0 star property
On-site Trails + Furnished Deck: Monteagle Escape!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

10/10 Excellent
"N/A"
Angela Marie 1-night trip
Posted 4 days ago
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

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.