Photo by Betsy Wood

Search Cottages in Winchester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 96 Cottages in Winchester with updated reviews, rates, and availability.

The Cottages at Golden Village Palms RV Resort
3 outdoor pools, pool umbrellas, sun loungers

The Cottages at Golden Village Palms RV Resort

3.0 star property
9.4 out of 10, Exceptional, (55)
"We come back every year and this year stayed at a cottage, great price, all ammenities included, run of the park and pools. Staff OUTSTANDING, shout out to Destiny and Joshua. Favorite place to stay to visit family in area"
The price is AED 555
AED 652 total
includes taxes & fees
14 Apr - 15 Apr
The Cottages at Golden Village Palms RV Resort
Cactus Garden Cottage…Best Location!!
Property grounds

Cactus Garden Cottage…Best Location!!

10.0 out of 10, Exceptional, (36)
"We had an excellent 2 night stay in this cute little cottage. We came up for a Friday afternoon wedding and were able to check in a little early to freshen up and change beforehand. Thank goodness, because it was pouring down rain! Margaret quickly responded to our questions and gave a great winery recommendation. The house was exactly as pictured, and the location was perfect. Would definitely stay again, especially since we joined 2 wine clubs while we were up there!"
The price is AED 459
AED 716 total
includes taxes & fees
14 Apr - 15 Apr
Cactus Garden Cottage…Best Location!!
Charming Cottage in the heart of Wine Country
Property grounds

Charming Cottage in the heart of Wine Country

10.0 out of 10, Exceptional, (51)
"The location was PRIME. It was in between all the wineries I needed to visit for a wedding weekend. Beautiful cottage with beautiful views! If I am to ever come back to the Temecula area, this would be my first choice stay!"
Charming Cottage in the heart of Wine Country
Madera Cottage
Fridge, microwave, stovetop, coffee/tea maker

Madera Cottage

10.0 out of 10, Exceptional, (118)
"I was in town by myself and stayed at this house. It was very cozy and charming. Very neat and clean, well decorated, and well stocked. I have no complaints and highly recommend this rental"
Madera Cottage
Lux Vineyard Escapes-Romantic Guest Suite
Terrace/patio

Lux Vineyard Escapes-Romantic Guest Suite

10.0 out of 10, Exceptional, (83)
"This place is beautiful and owners were very kind and helpful. I would absolutely recommend and look forward to staying again. "
Lux Vineyard Escapes-Romantic Guest Suite
Lake Elsinore Vacation Rental ~ 4 Mi to the Lake!
Interior

Lake Elsinore Vacation Rental ~ 4 Mi to the Lake!

3.0 star property
6.0 out of 10, (1)
"This home was very beautiful and met the needs of our family who flew into the area for a family memorial service, Frustrations with no remote for main tv, continual problem with lock on master bedroom, old dog poop in yard, very loud birthday party next door until 1 am Sat. night were some problems that detracted from our overall stay in this home. Host was communicative, and helpful most of the time. Overall we enjoyed our time here. It just could have been better if someone had made sure...
Lake Elsinore Vacation Rental ~ 4 Mi to the Lake!
Charming Fox Cottage w/ Wood Burning Fireplace
Fridge, microwave, oven, stovetop

Charming Fox Cottage w/ Wood Burning Fireplace

10.0 out of 10, Exceptional, (35)
"So cute and cozy- updated and andorable- easy check in - great appliances, kitchen necessities, bed, linens and bathroom. We already have recommended to friends!"
Charming Fox Cottage w/ Wood Burning Fireplace
Always Inn Idyllwild Vacation Cottages
Sleeping Beauty | Desk, iron/ironing board, free WiFi, bed sheets

Always Inn Idyllwild Vacation Cottages

3.0 star property
6.4 out of 10, (9)
"Great property, well kept, great for extended vacations"
The price is AED 1,168
AED 1,835 total
includes taxes & fees
14 Apr - 15 Apr
Always Inn Idyllwild Vacation Cottages
Charming 2-bedroom cottage in Fallbrook, CA with TV, WiFi, and AC.
Property grounds

Charming 2-bedroom cottage in Fallbrook, CA with TV, WiFi, and AC.

Charming 2-bedroom cottage in Fallbrook, CA with TV, WiFi, and AC.
Romantic, private and surrounded by best Wineries!
Fridge, microwave, oven, stovetop

Romantic, private and surrounded by best Wineries!

10.0 out of 10, Exceptional, (8)
"Quiet, close to wineries,"
The price is AED 915
AED 1,546 total
includes taxes & fees
14 Apr - 15 Apr
Romantic, private and surrounded by best Wineries!
Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3
Exterior

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

9.8 out of 10, Exceptional, (9)
"We had an amazing time! The animals were adorable and it was clean, quite and peaceful!! Will definitely be staying again"
The price is AED 918
AED 1,280 total
includes taxes & fees
14 Apr - 15 Apr
Namaste Farms; Private Working Wool Sheep Farm in Heart of Wine Country 501c3
Namaste Farms Wine Country Working Wool Sheep Farm; Main Cottage 501c3
Exterior

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

9.8 out of 10, Exceptional, (8)
"Surprised my wife with a trip to Temecula and found this lovely spot on a working farm. We both loved the atmosphere and the experience around the animals was incredible. The hosts were fantastic. Definitely recommend for an animal lover getaway or a cottage stay located close to every attraction/activity in the greater valley."
The price is AED 1,010
AED 1,425 total
includes taxes & fees
14 Apr - 15 Apr
Namaste Farms Wine Country Working Wool Sheep Farm; Main Cottage 501c3
The Cottage Haven - Nestled In The Heart Of Wine Country And Horse Country
Terrace/patio

The Cottage Haven - Nestled In The Heart Of Wine Country And Horse Country

9.8 out of 10, Exceptional, (142)
"This little cottage was very nice, clean and cozy. The decor was festive and we appreciated the beautiful Christmas tree. Four sisters were comfortable, felt safe and location was close to wine country, downtown Temecula, restaurants and stores. The backyard was very nice with plenty of places to sit or lounge. The jacuzzi was a plus! It was well stocked with everything you need. The stairs are a bit steep and I highly recommend the microwave be moved from on top of the refrigerator to the...
The Cottage Haven - Nestled In The Heart Of Wine Country And Horse Country
Idyllwild Cabin w/ Deck & Tahquitz Peak Views
Terrace/patio

Idyllwild Cabin w/ Deck & Tahquitz Peak Views

3.0 star property
Idyllwild Cabin w/ Deck & Tahquitz Peak Views
Buckley Farm Casita
Exterior

Buckley Farm Casita

10.0 out of 10, Exceptional, (8)
"This casita was just as described. It was very clean and had all the necessities. It was perfect for our needs and the location was close to our event. The host made check in easy even though we arrived later than expected. I appreciate the notes throughout the house on how to use different appliances, etc. The casita and back area was private enough to feel like we were own our own, but the host made sure we knew how to get a hold of her just in case we needed anything. She responded to...
Buckley Farm Casita
Fallbrook Airplane Home w/ Fire Pit & Mtn Views!
Interior

Fallbrook Airplane Home w/ Fire Pit & Mtn Views!

3.0 star property
Fallbrook Airplane Home w/ Fire Pit & Mtn Views!
Sleeps 4. Private casita in the country.
Fridge, microwave, oven, stovetop

Sleeps 4. Private casita in the country.

10.0 out of 10, Exceptional, (11)
"Carol & Joe, Thank you once again for providing a clean and perfect place for us and our dogs to stay while we enjoyed Thanksgiving with local family and friends. Have a Merry Christmas and a Prosperous New Year. We will see you again soon. Jon"
Sleeps 4. Private casita in the country.
SLEEP IN THE VINES! Perfect for 2 − 4 people!
Exterior

SLEEP IN THE VINES! Perfect for 2 − 4 people!

8.6 out of 10, Excellent, (13)
"Not described accurately. Needed two bedrooms since the companion accompanying me to the CE-5 conference snores loudly. Only one bedroom, only one bed. Friend slept on sofa. None of the other “rooms” qualify as a bedroom. No doors. Never got email about check in procedure. Got several indicating check in time and location. No information on unit amenities. Had to call Vrbo to find out about whether there was a coffeemaker available. The place had an odd odor upon entry."
SLEEP IN THE VINES! Perfect for 2 − 4 people!
Moonrise Cottage at Buena Terra Lavender Farm
Property grounds

Moonrise Cottage at Buena Terra Lavender Farm

10.0 out of 10, Exceptional, (5)
"Moonrise Cottage is a perfect place to escape every day stress and chaos. The remote location is very quiet and worth the effort. Cottage itself has a an eclectic decorating style. It’s got everything you need. Heidi is a wonderful host. I had lots of questions about directions etc. to get there and she was very prompt in answering and very clear on how to get there. My wife and I plan to return to this oasis."
The price is AED 826
AED 1,287 total
includes taxes & fees
14 Apr - 15 Apr
Moonrise Cottage at Buena Terra Lavender Farm
Adorable farm stay close to Temecula wine country
Fridge, microwave, oven, stovetop

Adorable farm stay close to Temecula wine country

10.0 out of 10, Exceptional, (10)
"The Casita was well acquainted, clean and beautiful. The hosts Amy and Frank were wonderful and were able to meet all of our needs. The farm had lots of room to run around with our dogs. We Are definitely going to book again with them Someday soon. ."
Adorable farm stay close to Temecula wine country
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!
Pool

5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!

10.0 out of 10, Exceptional, (19)
"Our family had an incredible stay at Daisy’s Resort & Retreat! The house was spacious enough for everyone to spread out and have their own space, which made our stay so much more enjoyable. The kitchen was well-stocked with everything we needed, making it easy to prepare meals and feel right at home.We spent time exploring Old Town Temecula, which was just a short drive away. The location is perfect – close to all the Temecula Wine Country wineries, Old Town, and Pechanga Resort Casino. Yet, the...
5 Mins to Temecula Wine Country; resort-like pool spa with amazing sunset views!
Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball
Pool

Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball

2.0 star property
9.0 out of 10, Wonderful, (4)
"Overall very clean, so much open space to do activities. Everyone was happy! They provided gifts for the guests and provided toiletries for everyone which was nice. If there were any issues, we’d call Sam and a representative would swing by the house to fix everything. So overall it was great for the entire group!"
The price is AED 3,599
AED 6,585 total
includes taxes & fees
14 Apr - 15 Apr
Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball
1/Bed Room Casita-Suite with Private Entrance
Outdoor pool

1/Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (39)
"Perfect for a quick overnight stay. "
The price is AED 213
AED 491 total
includes taxes & fees
14 Apr - 15 Apr
1/Bed Room Casita-Suite with Private Entrance
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.

Frequently asked questions

Why book your cottage in Winchester with Expedia?
We think that traveling 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 favorite 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.