Search Winchester Cottage Rentals from CA $286

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Check prices for these dates

Next weekend
Apr 4 - Apr 6
In two weeks
Apr 11 - Apr 13
In one month
Apr 25 - Apr 27
In two months
May 23 - May 25

Browse Select Winchester Cottages

Cottage with pool in historic downtown
Outdoor pool

Cottage with pool in historic downtown

10.0 out of 10, Exceptional, (198)
"Enjoyed our stay, relaxing outdoor space. Cottage was clean and had plenty of household supplies. "
Cottage with pool in historic downtown
Restful cottage close to antique shopping and mountain biking
Exterior

Restful cottage close to antique shopping and mountain biking

10.0 out of 10, Exceptional, (12)
"We were looking for the perfect place to stay for a girls’ weekend in Round Top and this was it ! The cabin was clean and cozy and had everything we needed. The layout is great and we loved sitting on the porch and drinking coffee in the mornings. The hosts were super nice and very hospitable - can’t wait to stay here again ! "
Restful cottage close to antique shopping and mountain biking
The White Magnolia Cottage
Dining

The White Magnolia Cottage

9.6 out of 10, Exceptional, (33)
"Very nicely appointed home, near Round Top. "
The price is CA $286
CA $345 total
includes taxes & fees
Apr 6 - Apr 7
The White Magnolia Cottage
Pool & Hot Tub in Sunny Smithville Getaway!
Interior

Pool & Hot Tub in Sunny Smithville Getaway!

3.0 star property
Pool & Hot Tub in Sunny Smithville Getaway!
Fishing Pond: Minervas Cottage in West Point!
Interior

Fishing Pond: Minervas Cottage in West Point!

2.0 star property
10.0 out of 10, Exceptional, (2)
"I just had an amazing weekend at this adorable cottage! Super clean, peaceful and quiet, gorgeous views of the sunset overlooking the pond, and some of the best hosts I've had the pleasure of renting from. Would absolutely stay here again and WILL! "
Fishing Pond: Minervas Cottage in West Point!
05 White Wing - Carmine Cottage with a Country View
Exterior

05 White Wing - Carmine Cottage with a Country View

10.0 out of 10, Exceptional, (6)
"Perfect little cabin only 5 minutes to downtown Round Top. Super clean! Had everything we needed. Would definitely stay here again. "
05 White Wing - Carmine Cottage with a Country View
Minutes from Round Top
Fridge, microwave, oven, stovetop

Minutes from Round Top

10.0 out of 10, Exceptional, (4)
"Great location for antique shopping in Warrenton. House was very clean and had everything we needed"
Minutes from Round Top
03 Ruby Redbird - Carmine Cottage with a Country View
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

03 Ruby Redbird - Carmine Cottage with a Country View

10.0 out of 10, Exceptional, (8)
"Nice quiet location"
03 Ruby Redbird - Carmine Cottage with a Country View
04 Bluemoon - Carmine Cottage with a Country View
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

04 Bluemoon - Carmine Cottage with a Country View

10.0 out of 10, Exceptional, (9)
"Thank you so much Eva and Bryan! I loved my time in this beautiful, cozy and well kept property!!! It’s perfect for a quick overnight or longer stay like mine! Your recommendations for eating & shopping were perfect and the property is conveniently located to restaurants, shops, wineries and all that Round Top and the surrounding area have to offer! I will be back very soon! Thanks again! "
04 Bluemoon - Carmine Cottage with a Country View
01 Lonestar - Carmine Cottage with a Country View
Exterior

01 Lonestar - Carmine Cottage with a Country View

10.0 out of 10, Exceptional, (7)
"Convenient location! Easy check in and clean room. Quiet property."
01 Lonestar - Carmine Cottage with a Country View
02 Yellow Rose - Carmine Cottage with a Country View
Exterior

02 Yellow Rose - Carmine Cottage with a Country View

9.6 out of 10, Exceptional, (5)
"The beer and wine bar was not open during our stay but the cabin was clean and perfect for our needs "
02 Yellow Rose - Carmine Cottage with a Country View
A-frame Cottage w/ Deck ~ 5 Mi to Lake Bastrop!
Cottage (2 Bedrooms) | Private kitchen

A-frame Cottage w/ Deck ~ 5 Mi to Lake Bastrop!

3.0 star property
A-frame Cottage w/ Deck ~ 5 Mi to Lake Bastrop!
Dock on Lake Siesta: Spacious La Grange Retreat!
Interior

Dock on Lake Siesta: Spacious La Grange Retreat!

3.0 star property
Dock on Lake Siesta: Spacious La Grange Retreat!
Hot Tub & Fire Pit: 'evergreen Escape' in Bastrop!
Interior

Hot Tub & Fire Pit: 'evergreen Escape' in Bastrop!

3.0 star property
Hot Tub & Fire Pit: 'evergreen Escape' in Bastrop!
Large Yard + Pond: Fayetteville Rural Retreat
Interior

Large Yard + Pond: Fayetteville Rural Retreat

3.0 star property
Large Yard + Pond: Fayetteville Rural Retreat
Charming 2-bedroom cottage in the magical Lost Pines forest with AC, WiFi
Private kitchen

Charming 2-bedroom cottage in the magical Lost Pines forest with AC, WiFi

2.0 star property
Charming 2-bedroom cottage in the magical Lost Pines forest with AC, WiFi
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

Pinehaven Luxury Glamping
Terrace/patio

Pinehaven Luxury Glamping

10.0 out of 10, Exceptional, (34)
"We loved this glamping tent!! Outfitted and decorated in simple elegance. The bed was ridiculously comfortable! Location was private and quiet, just right for our short getaway. Hosts were responsive and friendly. We will definitely be back!"
The price is CA $242
CA $331 total
includes taxes & fees
Apr 7 - Apr 8
Pinehaven Luxury Glamping
Adorable Guest Cabin In The Woods
Private kitchen

Adorable Guest Cabin In The Woods

10.0 out of 10, Exceptional, (41)
"We will stay there again sometime. Great quiet place to stay. Thanks again"
The price is CA $142
CA $209 total
includes taxes & fees
Apr 7 - Apr 8
Adorable Guest Cabin In The Woods
The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire
Terrace/patio

The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire

10.0 out of 10, Exceptional, (365)
"We felt secluded from town and people, just what we wanted. The gravel road entrance added to the 'country charm.' Sweet, comfortable and clean accomodations. Loved everthing about it!"
The price is CA $172
CA $304 total
includes taxes & fees
Apr 28 - Apr 29
The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire
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.