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Browse Select Winchester Cottages

Our top choices for Winchester cottages

The White Magnolia Cottage
Dining

The White Magnolia Cottage

9.8 out of 10, Exceptional, (41)
"A wonderful place to stay with a perfect location"
The price is CA $247
CA $290 total
includes taxes & fees
Sep 2 - Sep 3
The White Magnolia Cottage
Cottage with pool in historic downtown
Outdoor pool

Cottage with pool in historic downtown

10.0 out of 10, Exceptional, (205)
"I love this little cottage. Smithville is such a beautiful place to visit. Cottage with pool makes you seem that you are at your own private resort.i always feel that i have had a relaxing vacation. "
Cottage with pool in historic downtown
8 Minutes from Round Top! Your Silo-Bration Destination StoneHENge Silo #2
Exterior detail

8 Minutes from Round Top! Your Silo-Bration Destination StoneHENge Silo #2

9.8 out of 10, Exceptional, (39)
"We had fun again and we hope yo be back next year for the MS 150 ride"
The price is CA $309
CA $449 total
includes taxes & fees
Sep 2 - Sep 3
8 Minutes from Round Top! Your Silo-Bration Destination StoneHENge Silo #2
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, (18)
"WONDERFUL STAY!!! "
Restful cottage close to antique shopping and mountain biking
04 Bluemoon - Carmine Cottage with a Country View
Bar (on property)

04 Bluemoon - Carmine Cottage with a Country View

10.0 out of 10, Exceptional, (9)
"Property and stay was excellent, will definitely be back! Everything was clean and had everything we needed. Owners left great instructions and made the stay easy! "
04 Bluemoon - Carmine Cottage with a Country View
05 White Wing - Carmine Cottage with a Country View
Bar (on property)

05 White Wing - Carmine Cottage with a Country View

10.0 out of 10, Exceptional, (6)
"Great place! Cute and clean and well located"
05 White Wing - Carmine Cottage with a Country View
Fishing Pond: Minervas Cottage in West Point!
House (1 Bedroom) | 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!
03 Ruby Redbird - Carmine Cottage with a Country View
Bar (on property)

03 Ruby Redbird - Carmine Cottage with a Country View

10.0 out of 10, Exceptional, (9)
"This cabin was in a great location, easy to access where we wanted to go. It was clean and had all the items that we would need for our stay."
03 Ruby Redbird - Carmine Cottage with a Country View
02 Yellow Rose - Carmine Cottage with a Country View
Bar (on property)

02 Yellow Rose - Carmine Cottage with a Country View

9.6 out of 10, Exceptional, (5)
"Sweet spot to visit the tiny Texas town of Round Top."
02 Yellow Rose - Carmine Cottage with a Country View
Pool & Hot Tub in Sunny Smithville Getaway!
House (2 Bedrooms) | Interior

Pool & Hot Tub in Sunny Smithville Getaway!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Really nice place!! Close to several small towns for day trips…sat on deck for morning coffee! Host was very responsive!!"
Pool & Hot Tub in Sunny Smithville Getaway!
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
01 Lonestar - Carmine Cottage with a Country View
Bar (on property)

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
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!
8 Minutes from Round Top! Your Silo-Bration Destination COOP-A-Cabana Silo #3
1 bedroom, free WiFi, bed sheets

8 Minutes from Round Top! Your Silo-Bration Destination COOP-A-Cabana Silo #3

9.8 out of 10, Exceptional, (59)
"Beautifully anointed silo! Wonderful accommodations for a country excursion!"
The price is CA $309
CA $449 total
includes taxes & fees
Sep 2 - Sep 3
8 Minutes from Round Top! Your Silo-Bration Destination COOP-A-Cabana Silo #3
Charming 1-bedroom cottage 8 minutes from Round Top-WiFi, AC -zHEN House Silo #1
1 bedroom, free WiFi, bed sheets

Charming 1-bedroom cottage 8 minutes from Round Top-WiFi, AC -zHEN House Silo #1

9.8 out of 10, Exceptional, (26)
"Perfect little cottage style lodging in a beautiful area."
The price is CA $309
CA $449 total
includes taxes & fees
Sep 2 - Sep 3
Charming 1-bedroom cottage 8 minutes from Round Top-WiFi, AC -zHEN House Silo #1
Dock on Lake Siesta: Spacious La Grange Retreat!
House (4 Bedrooms) | 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!
House (3 Bedrooms) | 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
House (1 Bedroom) | Interior

Large Yard + Pond: Fayetteville Rural Retreat

3.0 star property
Large Yard + Pond: Fayetteville Rural Retreat
The Sloan - Farmstead
1 bedroom, WiFi, bed sheets

The Sloan - Farmstead

The price is CA $353
CA $512 total
includes taxes & fees
Sep 2 - Sep 3
The Sloan - Farmstead
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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Top Winchester Hotel Reviews

Find out more about Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
Accommodation
27 Cottages
Lowest Price
CA $247
Highest Price
CA $353

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