Search Winchester Cottage Rentals from CA $286

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Check prices for these dates

Next weekend
Jan 31 - Feb 2
In two weeks
Feb 7 - Feb 9
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Feb 21 - Feb 23
In two months
Mar 21 - Mar 23

Browse Select Winchester Cottages

Cottage with pool in historic downtown
Outdoor pool

Cottage with pool in historic downtown

10.0 out of 10, Exceptional, (196)
"Excellent cottage in a quiet secluded neighborhood."
Cottage with pool in historic downtown
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 $340 total
includes taxes & fees
Jan 26 - Jan 27
The White Magnolia Cottage
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, (11)
"This place was so adorable!! They truly thought of everything when putting this place together. Coffee, makeup towels, a vanity for the girls, etc. we loved it and will likely stay again in the future. The hosts were quick to respond and kind. :)"
Restful cottage close to antique shopping and mountain biking
01 Lonestar - Carmine Cottage with a Country View
Exterior

01 Lonestar - Carmine Cottage with a Country View

10.0 out of 10, Exceptional, (5)
"Only 3.7 miles to center of Round Top! Very clean! Enjoyed our stay!"
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
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
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
A-Frame Cottage w/ Deck ~ 5 Mi to Lake Bastrop!
Microwave, stovetop, dishwasher, coffee/tea maker

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

10.0 out of 10, Exceptional, (1)
"I was blown away by the attention to details provided for our comfort and enjoyment. I’m an aficionado of vacation rentals, and I know what appeals to guests. This property is well stocked, has creature comforts and pluses like snacks, water, condiments, and spices for your kitchen needs, and it has a lovely deck for outdoor sunset relaxation or dining European style. The laundry room is chic, as are the sitting nooks and office space in the A Frame loft. This property is definitely my new...
A-Frame Cottage w/ Deck ~ 5 Mi to Lake Bastrop!
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
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!
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, (8)
"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
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!
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!
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

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, (362)
"Absolutely loved our stay! One of our favorites so far! Very dog friendly. Our girls loved walking the trails and playing back at the cabin in the fenced in area. Felt completely safe letting them off leash to play. The Cabin is super cute and well stocked with some basics for humans and fur babies! Thank you so much for your hospitality! "
The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire
Pinehaven Luxury Glamping
Terrace/patio

Pinehaven Luxury Glamping

10.0 out of 10, Exceptional, (31)
"Great rental, well-appointed safari tent"
The price is CA $242
CA $333 total
includes taxes & fees
Jan 26 - Jan 27
Pinehaven Luxury Glamping
Cottage with pool in historic downtown
Outdoor pool

Cottage with pool in historic downtown

10.0 out of 10, Exceptional, (196)
"Excellent cottage in a quiet secluded neighborhood."
Cottage with pool in historic downtown
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.