Photo by Betsy Wood

Search Winchester Cabins

  • 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
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Cabin Rentals in Winchester

Cozy Cottage, on the creek w/ hot tub!

8.8 out of 10, Excellent, (26)
"Very convenient location and a really beautiful property."
Cozy Cottage, on the creek w/ hot tub!

Pet friendly cabin-Fully fenced yard! Pets stay free!

10.0 out of 10, Exceptional, (174)
"House is the perfect size for a couple getaway, and for us our 1 dog. Located just outside the village, in a super quiet neighborhood. The main living area is spacious, and has the bed, sofa, and small dining table. Out back is the kitchen and bathroom. Decent size yard that is truly fully fenced in that you can safely leave your dog. Plenty of squirrel watching! This place is great value and well recommended. We'll be back!"
Pet friendly cabin-Fully fenced yard! Pets stay free!

5 STAR **STRAWBERRY CORNER** CLASSIC CABIN ON CREEK, 1 MINUTE WALK TO VILLAGE!

9.8 out of 10, Exceptional, (297)
"Beautiful, cozy property. Great location, pet friendly yard and had everything we needed. We look forward to staying again. "
5 STAR **STRAWBERRY CORNER** CLASSIC CABIN ON CREEK, 1 MINUTE WALK TO VILLAGE!

Fully fenced backyard for pets. Pets stay free!

10.0 out of 10, Exceptional, (71)
"The space is pretty big if it's just you and your partner. Layla and Suki loved the yard and the fire pit being in the center of it was legit. The place is super close to town and all of the bigger trails. Jay and Darlene were such great communicators and their recommendations are absolutely solid. 10/10 will be staying here again to check out more of the area."
Fully fenced backyard for pets. Pets stay free!

ROMANTIC LOG CABIN ~ Quiet, Clean, Cozy ~Walk to Trails, 3 Min to Town!

10.0 out of 10, Exceptional, (227)
"This property is a great location. Wonderful place to relax and apend time with nature. Property owner is super helpful and the property itself was stocked with everything that we needed and the owner was super helpful even giving us a warning of potential surprise snow the day we left."
ROMANTIC LOG CABIN ~ Quiet, Clean, Cozy ~Walk to Trails, 3 Min to Town!

Coral Tree House

3.0 star property
10.0 out of 10, Exceptional, (19)
"It was peaceful and beautiful! It’s a great place to just escape for a little while "
Coral Tree House

Dog-friendly cabin in the woods with WiFi, wood stove, and private washer/dryer

9.6 out of 10, Exceptional, (76)
"Property was better than advertised! The upstairs loft has a queen bed plus 4 twins. My kids loved this space. Our only snafu was the pilot light going out on the water heater, but the management company had someone out to fix it within 30 minutes. Less than 5 minutes to town but you feel a world away. We'd definitely be interested in coming back."
Dog-friendly cabin in the woods with WiFi, wood stove, and private washer/dryer

Knotting Hill Amazing View and Spa

8.8 out of 10, Excellent, (65)
"Was a little rocky checking in but they made sure we were happy and were more than accommodating and kind. I would definitely stay here again and work with them again. "
Knotting Hill Amazing View and Spa

Hikers Hideaway Lodge

8.8 out of 10, Excellent, (3)
"Overall great stay. Fenced in property. Property manager was easily reached when needed and was very helpful. Very clean property. Would 100% stay here again. "
The price is NZ$789
includes taxes & fees
15 Apr - 16 Apr
Hikers Hideaway Lodge

Charming 1937 Vintage Cottage 2 bedrooms/ baths,(Sleeps 4) walk to town/creek

9.2 out of 10, Wonderful, (33)
"Charming vintage cabin with an over abundance of cabin decor- we counted 55 word/phrase signs /sayings on the walls, 28 bears, 16 squirrels, 8 moose/deer, 10 owls and 28 birds. There is a lot of personal stuff and not many places or surface area for their guests to use. BIG downside- only the primary bathroom shower works- the 2nd bathroom only has a tub with no shower. This was a big deal for us as the 2 full bathrooms was the main reason we rented this place. Communication was not great due to...
Charming 1937 Vintage Cottage 2 bedrooms/ baths,(Sleeps 4) walk to town/creek

A beautifully wild, pet friendly, fully fenced cabin with a hot tub

9.2 out of 10, Wonderful, (24)
"Our family stayed for three nights for my husband's birthday. Our host was excellent with communication and very helpful. The place was a little smaller than we expected but we didn't mind it. This is a pet friendly house so every now and then you get a faint smell of that. We arrived while it was snowing and even though our host had already plowed the driveway it was full of snow again and we had a hard time getting up the steep driveway, even with chains (something to be aware of if you're...
A beautifully wild, pet friendly, fully fenced cabin with a hot tub

Idyllic Mountain Cabin

9.8 out of 10, Exceptional, (22)
"Such a nice beautiful little cabin for two. Great location, well stocked kitchen, clean and comfortable!"
Idyllic Mountain Cabin

Almost Heaven! A charming cabin on the creek walk to town with spa

9.4 out of 10, Exceptional, (59)
"This is a great house centrally located to town with plenty of space and privacy for a big group. The exterior deck is massive and such a great place to take in nature of idyllwild but in comfort. When/if traveling with a group for 6 or more people, I would definitely book this house again. The kitchen was well stocked with necessary dish and cookware. The heater worked great. And the house had plenty of games, puzzles, and a TV for entertainment. Wifi also worked great. The only downside is...
Almost Heaven! A charming cabin on the creek walk to town with spa

Stunning Idyllwild Home w/ Private Hot Tub & Decks

9.8 out of 10, Exceptional, (51)
"We had an amazing stay at the cabin from March 26 to April 1, 2025. Our family of six thoroughly enjoyed the beautiful, clean, and well-stocked accommodations. The kids had a blast playing games, while we took advantage of the hot tub, deck, and the stunning views surrounding us. It's a perfect spot for relaxation and family fun. I would highly recommend this cabin to anyone looking to explore and enjoy the area."
Stunning Idyllwild Home w/ Private Hot Tub & Decks

Secluded Dog-Friendly Cabin w/Wood Fireplace, Deck, Private W/D, Mtn Views

9.6 out of 10, Exceptional, (59)
"This cabin feels like home. All the necessities have been provided. The only plus would be a dishwasher. Otherwise, it’s close to perfect. "
Secluded Dog-Friendly Cabin w/Wood Fireplace, Deck, Private W/D, Mtn Views

Dawson Haven w/spa, game room on .34 acres

8.8 out of 10, Excellent, (5)
"Great location for a girls trip. Close to town, yet secluded enough for privacy. "
Dawson Haven w/spa, game room on .34 acres

The Little Cabin 🌲The coziest cabin on the Mountain.

10.0 out of 10, Exceptional, (81)
"Hosts were fantastic and very proactive. The cabin was just as advertised. Really nice property in the trees. Had a very relaxing time and the town and locals in idyllwild are great. Very friendly licsls and good restaurants. "
The Little Cabin 🌲The coziest cabin on the Mountain.

"Cozy Oaks Cabin" Peaceful Mountain Getaway, Charming & Romantic! Trail Pass...

10.0 out of 10, Exceptional, (225)
"Honestly, one of the best rental houses we've ever stayed in. These people are HOSTS! They had everything so dialed in in this cabin. Felt like a real home. So many amenities, detailed instructions for anything you could need. Dining, activities, hikes, history, anything you could think of they've gotchu covered. Mike and Sue are the best. WE WILL BE BACK!"
"Cozy Oaks Cabin" Peaceful Mountain Getaway, Charming & Romantic! Trail Pass...

Adorable cabin in the trees near hiking & town w/ deck & high-speed WiFi

9.6 out of 10, Exceptional, (59)
"A delightful house, well stocked with all we needed. The mini-splits were a nice touch to have heat where we needed and the main part of the house stayed warm with just the log stove going. The bedroom heaters were a bit noisy but overall a great stay!"
Adorable cabin in the trees near hiking & town w/ deck & high-speed WiFi

Spacious Private 2 Bedrooms 2 bathrooms Cabin with Hot Tub

9.0 out of 10, Wonderful, (25)
"start with the positives. cabin had good amenities, was clean. Even though we brought some stuff, it had plenty of towels, kitchen appliances, extra blankets, coffee etc. The hot tub was clean worked well, and was the perfect way to end a day of hikes and shopping. Cabin was also in a good quiet neighborhood just far enough from the main center of town for some peace and quiet but super close.As for the negatives, I wish i could get at least a refund on my first night. We got to the area early...
Spacious Private 2 Bedrooms 2 bathrooms Cabin with Hot Tub
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

Other property types in Winchester

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

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 NZ$3,078
includes taxes & fees
14 Apr - 15 Apr
Retro Ranch-10bd-Pool-Hot Tub-Games-Pickleball

1/Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (39)
"Perfect for a quick overnight stay. "
The price is NZ$230
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

What are the best cabins near Winchester?
Spend time in the great outdoors without surrendering home comforts at one of our 3 997 cabins in and around Winchester. Whether you have relaxation or adventure on your mind, Cosy Oaks Cabin” Peaceful Mountain Getaway offers both. Alternatively, stay at Cabin - 210 Five Star Reviews Directly Across From Lake and kick back among picturesque surroundings.
Are there cheap cabins in Winchester?
Whether you’d love to stay steps from the water or up a mountain, we have an awesome selection of cheap cabins in Winchester to suit. Priced from NZ$789 to NZ$789 a night, your ideal cabin is waiting right here.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best luxury cabins near Winchester?
Splash out and enjoy a stay that’s hard to forget at one of our Winchester luxury cabins. Family Cabin: Hot Tub, Firepit is one option where you can spend a couple of days or so indulging your fondness for the finer things in life. It features a spa tub and a firepit. Alternatively, use Whisky Mountain Lodge At Big Bear W as a base to explore the beautiful natural areas around you. Amenities here include a deck and a king-sized bed.
What are the best river cabins near Winchester?
If you’re looking for a comfortable getaway moments from the water, a Winchester river cabin is an excellent choice. Kick back at Moon Escape Family Retreat~ Castle Rock Trail Cabin and let any worries on your mind take a hike downstream. Useful amenities here include snowsport activities and a nearby marina. Another popular riverside rental is Cabin - Romantic Chic Dutch Décor, Fenced Yard. Its conveniences include a wood stove, snowsport activities and more.
What are the best cabins with pools near Winchester?
If you like the thought of every day being a pool day, make your way to Lakeside Family Cabin At Shore Acres Lodge Big Bear. It’s one of our leading cabin rentals with a pool near Winchester and comes with useful amenities like a swimming pool and a patio. Little Pines Couples Lakeside Cottage At Big Bear Lake is another popular place to spend leisurely days poolside. A swimming pool, a patio and fun times are what you can expect here.
Can I find beach cabins near Winchester?
Enjoy your fix of salt air and sunshine at Lake Arrowhead Lakefront Cabin Winter Wonderland. One of our popular Winchester beach cabins, it offers beach sun loungers and clothes washing facilities. You can also spend laid-back days along the shore at Cabin - Breezy One Lakeside Retreat At Big Bear Lake. Parking facilities and clothes washing facilities will make your visit extra comfortable.
What are the best weekend cabin rentals in Winchester?
Whether you’re planning a quick trip with that special someone or the whole crew, we’ll help you find the perfect weekend cabin getaway. One top example? Beautiful Log Cabin With Views. Featuring a patio and a fireplace, you’ll appreciate the natural setting here. Cabin - Children And Dogs Heavenly Retreat is another fantastic place where you can slow things down. Spend a couple of nights at this retreat which offers a patio and a fireplace.
What are the best cabin prices in Winchester?
If you’d rather save on your stay, Expedia has some incredible deals on Winchester cabins that won’t break the bank. Like the sound of NZ$789 a night?
Can I find log cabins in Winchester?
For some adventurers, the ideal outdoor holiday just isn’t complete without bunking down in a log cabin full of charm and character. Go adventuring or just slow down and relax at Beautiful Log Cabin With Views. Recreational activities such as sailing and sky diving are on your doorstep here. Another log cabin getaway is Freedom Village Lodge By Destination Big Bear : Log Cabin Near Ski Slopes. Surfing and kite surfing will keep you occupied when you’re not resting up in your rustic digs.
What are the highest-rated cabins in Winchester?
There are some holiday rentals that tick just about every box. Cabin - Mountain View: Gorgeous Views, Ac is a superb example. With an impressive rating, it comes with useful amenities like a patio and a fireplace. Another top option is Everett Retreat Cabin: Spacious Kitchen. A patio and a fireplace are just some of the conveniences to look forward to here.
Why should I book a cabin in Winchester?
For a retreat that’s big on character, home comforts and affordability, a cabin is the best choice. Leave your city blues behind and roam through the greenery of the great outdoors. From days spent rambling to peaceful nights curled up by the fireplace, cabins promise both excitement and relaxation. Check out the wonderful Winchester options here on Expedia.
What are the top nature cabins in Winchester?
Featuring plenty of charm and creature comforts, Moon Escape Family Retreat~ Castle Rock Trail Cabin is among our top nature cabins in Winchester. But with a whole bunch of things to see and do nearby, make sure you don’t spend all your time relaxing indoors. Activities including paddle boating and nearby sailing await. Cabin - Romantic Chic Dutch Décor, Fenced Yard is another rental where you can hang out in nature. Skiing and nearby hiking and biking trails are a couple of fun ways to do it.