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Find Cabins in Winchester for Rent

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Check prices for these dates

Next weekend
Mar 21 - Mar 23
In two weeks
Mar 28 - Mar 30
In one month
Apr 11 - Apr 13
In two months
May 9 - May 11

Browse Select Winchester Cabin Rentals

Retro Ranch Cottage 800sf Pool HotTub Pickleball
Pool

Retro Ranch Cottage 800sf Pool HotTub Pickleball

9.0 out of 10, Wonderful, (2)
"This cottage was amazing! Not only was it super clean but the decor was great and host was awesome! Very attentive and accommodating with any requests. The pool and outdoor area beautiful and everyone enjoyed there stay. We would definitely book another stay!"
Retro Ranch Cottage 800sf Pool HotTub Pickleball
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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Other property types in Winchester

Chateau Vino - French Style Chalet
Exterior

Chateau Vino - French Style Chalet

10.0 out of 10, Exceptional, (36)
"Very friendly host. Very spacious, quiet place. Perfect for our family for my son's wedding in Fallbrook. "
Chateau Vino - French Style Chalet
1/Bed Room Casita-Suite with Private Entrance
Outdoor pool

1/Bed Room Casita-Suite with Private Entrance

9.8 out of 10, Exceptional, (38)
"This casita was the most perfect place for me to stay. The host, Elizabeth, sure packs a punch in the casita with everything you could possibly need. Relaxing, beautiful, quiet and safe. Elizabeth was very communicative before my arrival and during my stay. Very responsive. I would definitely stay here again, over and over. Thank you Elizabeth and VRBO for offering this casita. "
The price is CA $84
CA $193 total
includes taxes & fees
Mar 17 - Mar 18
1/Bed Room Casita-Suite with Private Entrance
Wine Country Resort - Close to Wineries
Outdoor pool

Wine Country Resort - Close to Wineries

Wine Country Resort - Close to Wineries
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?
Ranging from quaint and compact to large and luxurious, you have 3,826 cabins to pick from in and around Winchester. Top options include Cozy Oaks Cabin” Peaceful Mountain Getaway and Cabin - Across From Lake 200 Five Star Reviews Jacuzzi.
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 to 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?
Splurge a little and enjoy a stay that’ll be hard to forget at one of our Winchester luxury cabins. Family Cabin: Hot Tub, Firepit is one option where you can spend your break appreciating the finer things. It comes with a spa tub and a firepit. Or, use Whiskey Mountain Lodge- Relaxing Chalet- Hot Tub as a base to discover the beautiful natural areas around you. Quality amenities here include a deck and a king-sized bed.
What are the best river cabins near Winchester?
If you’re in search of a comfortable getaway moments from the water, a Winchester river cabin will be just the thing. Recharge your batteries at Moon Escape Family Retreat~ Castle Rock Trail Cabin~ and let any stresses float away downstream. Useful amenities here include snowsport activities and a nearby marina. Another top riverside property is Cabin - Romantic Chic Dutch Décor, Fenced Yard. Guests have use of a wood stove, snowsport activities and more.
What are the best cabins with pools near Winchester?
Staying in a cabin rental with a pool adds even more fun to your vacation. If you’re seeking one near Winchester, Lakeside Family Cabin At Shore Acres Lodge Big Bear offers conveniences like a swimming pool and a patio to make your poolside getaway even more memorable. Little Pines Cabin At Shore Acres is another top choice and features a swimming pool and a patio.
Can I find beach cabins near Winchester?
Wake up and be within easy reach of the sparkling sea when you lock in a stay at a Winchester beach cabin rental. Sunshine and fun should be your major priorities at Lake Arrowhead Lakefront Cabin With Beach And Oktoberfest. It comes with beach sun loungers and clothes washing facilities. Or, throw your bag down and kick your feet up at Breezy One Lakeside Family Cabin At Big Bear. Handy amenities here include parking facilities and clothes washing facilities.
What are the best weekend cabin rentals in Winchester?
Whether you’re organizing a whirlwind trip with your sweetheart or the whole crew, we’ll help you find the best weekend cabin getaway. One superb example? 1 Acre Franksfort Mountain Retreat By Destination Big Bear : 1. 25 Acre Resort With Spa. Featuring on-site watersports and a patio, you’ll adore the natural surroundings here. Cabin - Windsong Retreat By Destination Big Bear : Luxurious Panoramic Views Central A is another fantastic place where you can hit pause. Enjoy a few nights at this retreat which offers on-site watersports and a patio.
What are the best cabin prices in Winchester?
Whether you’re pinching your pennies or want to splash out on your next trip, you’ll find what you’re looking for with Expedia. At the moment, you can score a Winchester cabin from only a night.This price was 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.
Can I find log cabins in Winchester?
For lots of nature lovers, the perfect outdoor vacation isn’t complete without bunking down in a log cabin full of charm and character. Go adventuring or simply relax and unwind at Beautiful Log Cabin With Views. Recreational activities such as cycling and mountain climbing are among the exciting things to do here. Another log cabin getaway is Freedom Village Lodge by Destination Big Bear : Log Cabin Near Ski Slopes, Village & Lake! Game Room! Spa! Foosball! Privacy!. Snowboarding and sunbathing will keep you occupied when you’re not kicking back in your rustic digs.
What are the highest-rated cabins in Winchester?
There are some cabin rentals that are hard to fault. Mountain View: Gorgeous Views, AC, Jacuzzi bathtub! is a good example. With such an impressive rating, it comes with useful amenities like a patio, a fireplace and much more. Another excellent option is Everett Retreat Cabin: Spacious Kitchen, Indoor Outdoor Living. A patio and a fireplace are a few of the conveniences waiting for you 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?
The outdoors won’t be the only thing you’ll be surrounded by when you choose a nature cabin in Winchester. Adventure is everywhere you look too. Take off to Moon Escape Family Retreat~ Castle Rock Trail Cabin~ and find time for hiking and nearby mountain biking. Another option to consider is Cabin - Romantic Chic Dutch Décor, Fenced Yard. It’s known for its creature comforts along with its nearby sledding and jet skiing opportunities nearby.