Lodging Image

Search Winchester Cottages

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Winchester cottages

A single-story house with a porch, a small garden, and a vehicle parked outside.

1. The Cottages at Golden Village Palms RV Resort

The Cottages at Golden Village Palms RV Resort
3.0 star property
Hemet
9.2 out of 10, Wonderful, (113 reviews)
"Staff was very friendly , very clean , beautiful place"
United States
Albert
The price is £133
includes taxes & fees
4 Nov - 5 Nov
The Cottages at Golden Village Palms RV Resort
A covered outdoor area with a wooden deck, a chair, a potted plant, and a view of a hilly landscape.

2. Rejuvenation Cottage -Wine Country Tranquility

Rejuvenation Cottage -Wine Country Tranquility
Valle De Los Caballos
10.0 out of 10, Exceptional, (3 reviews)
"The location was beautiful. It was quiet and clean. I would come back again.. it had all the amenities needed, very comfortable bed, and a great bathroom. There’s excellent communication between the hosts and the directions were easy."
United States
Christa F.
Rejuvenation Cottage -Wine Country Tranquility
A single-story house with a white exterior, a red-tiled roof, and a garage. There are hanging flower baskets above the entrance and a small garden area with a wooden planter.

3. Romantic, private and surrounded by best Wineries!

Romantic, private and surrounded by best Wineries!
GlenOak Hills
10.0 out of 10, Exceptional, (31 reviews)
"We loved our stay! Home was clean, comfortable, and the decor was amazing!"
United States
Dana O.
The price is £298
includes taxes & fees
1 Nov - 2 Nov
Romantic, private and surrounded by best Wineries!
A wooden cabin with a porch, a potted plant, and a hanging flower basket.

4. Namaste Farms Wine Country Working Wool Sheep Farm; Main Cottage 501c3

Namaste Farms Wine Country Working Wool Sheep Farm; Main Cottage 501c3
Valle De Los Caballos
10.0 out of 10, Exceptional, (11 reviews)
"This property is so cute. I wish I had more time to stay. Loved having all the farm animals."
United States
Christina D.
The price is £294
includes taxes & fees
28 Oct - 29 Oct
Namaste Farms Wine Country Working Wool Sheep Farm; Main Cottage 501c3
A rustic cabin with a porch, surrounded by trees and a gravel driveway.

5. Always Inn Idyllwild Vacation Cottages

Always Inn Idyllwild Vacation Cottages
3.0 star property
Fern Valley
7.0 out of 10, Good, (12 reviews)
"Great property, well kept, great for extended vacations"
United States
Domonick
The price is £338
includes taxes & fees
15 Nov - 16 Nov
Always Inn Idyllwild Vacation Cottages
A house with a satellite dish, a garage, and potted plants in the front yard.

6. Hike, Sip & Explore: Couples Retreat in Fallbrook

Hike, Sip & Explore: Couples Retreat in Fallbrook
3.0 star property
Fallbrook
The price is £200
includes taxes & fees
9 Nov - 10 Nov
Hike, Sip & Explore: Couples Retreat in Fallbrook
A rustic wooden cabin with a stone-paved entrance, a porch with a bench, and potted plants.

7. Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3

Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3
Valle De Los Caballos
9.8 out of 10, Exceptional, (9 reviews)
"We had an amazing time! The animals were adorable and it was clean, quite and peaceful!! Will definitely be staying again"
United States
Chloe D.
The price is £261
includes taxes & fees
2 Nov - 3 Nov
Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3
A wooden deck with outdoor furniture, including chairs and a table, surrounded by greenery and trees.

8. Moonrise Cottage at Buena Terra Lavender Farm

Moonrise Cottage at Buena Terra Lavender Farm
Valley Center
10.0 out of 10, Exceptional, (8 reviews)
"The place was awesome super beautiful place and the hosts are very kind and welcoming!"
United States
Matthew S.
The price is £251
includes taxes & fees
5 Nov - 6 Nov
Moonrise Cottage at Buena Terra Lavender Farm
A patio with Adirondack chairs and a red building in the background.

9. Farm Stay Bungalow And Hot Tub

Farm Stay Bungalow And Hot Tub
Rainbow
10.0 out of 10, Exceptional, (17 reviews)
"We only stayed one night, but this bungalow was the perfect little getaway. The animals on the farm are so cool and you really can't beat the views. It was clean and the produce they gave us was so delicious. I would definitely stay again!"
United States
Jen A.
The price is £604
includes taxes & fees
28 Oct - 29 Oct
Farm Stay Bungalow And Hot Tub
Outdoor dining

10. Pet Friendly Charming Cottage with Incredible Views and Hot-tub in Rainbow, California

Pet Friendly Charming Cottage with Incredible Views and Hot-tub in Rainbow, California
Fallbrook
The price is £375
includes taxes & fees
28 Oct - 29 Oct
Pet Friendly Charming Cottage with Incredible Views and Hot-tub in Rainbow, California
A house with a swimming pool, a patio with chairs and a table, and a covered area with a door.

11. Charming, quiet cottage in brilliant Fallbrook with AC, WiFi, private, Smart TV.

Charming, quiet cottage in brilliant Fallbrook with AC, WiFi, private, Smart TV.
Fallbrook
The price is £1,720
includes taxes & fees
29 Oct - 30 Oct
Charming, quiet cottage in brilliant Fallbrook with AC, WiFi, private, Smart TV.
A hot tub with a wooden deck, surrounded by Adirondack chairs, set against a backdrop of trees and mountains.

12. Pet Friendly Breathtaking Cottage with Hot-tub in Rainbow, California

Pet Friendly Breathtaking Cottage with Hot-tub in Rainbow, California
Fallbrook
The price is £365
includes taxes & fees
28 Oct - 29 Oct
Pet Friendly Breathtaking Cottage with Hot-tub in Rainbow, California
Property grounds

13. Pet Friendly Breathtaking Cottage with Great Views and Hot-tub in Rainbow, California

Pet Friendly Breathtaking Cottage with Great Views and Hot-tub in Rainbow, California
Fallbrook
The price is £468
includes taxes & fees
29 Oct - 30 Oct
Pet Friendly Breathtaking Cottage with Great Views and Hot-tub in Rainbow, California
Outdoor spa tub

14. Pet Friendly Fantastic Cottage with Hot-tub in Rainbow, California

Pet Friendly Fantastic Cottage with Hot-tub in Rainbow, California
Fallbrook
The price is £342
includes taxes & fees
29 Oct - 30 Oct
Pet Friendly Fantastic Cottage with Hot-tub in Rainbow, California
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

Tahquitz Pines Retreat

Tahquitz Pines Retreat

8/10 Good
"We had a great stay. Staff in the front desk was courteous and friendly. Dog friendly was definitely a plus! Thank you for the hospitality."
William 3-night trip
Posted 7 hours ago
Tahquitz Pines Retreat

Find out more about Winchester

Winchester Cottages information

Number of reviews
175
Accommodation
108 Cottages
Lowest Price
£133
Highest Price
£1,720

Frequently asked questions

Why book your cottage in Winchester with Expedia?
We think that travelling should be stress-free, so if you're in search of cottages in Winchester at a nice price, Expedia has you covered. Keep the budget in check and select an economical option far from the downtown buzz, or splurge on an upmarket cottage to spoil your favourite people.
How can I find cheap cottages in Winchester?
With Expedia's useful filter tool, scoring cheap cottages in Winchester is a cinch. To find stays that are very pocket friendly, narrow your search results by budget, amenities and star rating.