Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Winchester vacation rentals

Exterior

Adorable Guest Cabin In The Woods

Adorable Guest Cabin In The Woods
La Grange
9.8 out of 10, Exceptional, (71 reviews)
"Quiet and close to nature. "
United States
Andy
The price is ￥14,202
￥21,622 total
includes taxes & fees
Mar 30 - Mar 31
Adorable Guest Cabin In The Woods
Property grounds

Cozy Cottage With a View in La Grange

Cozy Cottage With a View in La Grange
La Grange
10.0 out of 10, Exceptional, (11 reviews)
"The Garden Cottage was a great little getaway spot!Very clean and had all the essentials!"
United States
Kyle J.
The price is ￥14,345
￥23,462 total
includes taxes & fees
Apr 1 - Apr 2
Cozy Cottage With a View in La Grange
1 bedroom, WiFi, bed sheets

Swiss Alp Texas Cabin

Swiss Alp Texas Cabin
Schulenburg
9.8 out of 10, Exceptional, (9 reviews)
"The place was lovely and communication with the host was so quick and helpful! Highly recommend!"
United States
Tracey C.
The price is ￥17,931
￥26,419 total
includes taxes & fees
Mar 31 - Apr 1
Swiss Alp Texas Cabin
Interior

Pinehaven Luxury Glamping

Pinehaven Luxury Glamping
La Grange
10.0 out of 10, Exceptional, (55 reviews)
"It was a very nice place to stay."
United States
Mike M.
The price is ￥23,749
￥33,430 total
includes taxes & fees
Apr 7 - Apr 8
Pinehaven Luxury Glamping
Children's area

Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await

Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
Paige
9.8 out of 10, Exceptional, (20 reviews)
"The property at Blessing Ranch in Paige, Tx was Very relaxing and peaceful. Not too far from dining and shopping, yet off the main road for privacy. The house is immaculate with all modern finishes and appliances. Very comfortable beds. Exceeded my expectations."
United States
Richard
The price is ￥23,909
￥49,650 total
includes taxes & fees
Apr 13 - Apr 14
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
Property grounds

The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire

The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (232 reviews)
"Fantastic stay! The treehouse is quite charming with thoughtful Tolkien touches. The property is secluded and makes you feel as though you have the place all to yourself. Would definitely stay again!"
United States
Allen L.
The price is ￥21,677
￥37,326 total
includes taxes & fees
Mar 29 - Mar 30
The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire
Interior

Elm Grove Camper- Less than 3 miles from Round Top proper

Elm Grove Camper- Less than 3 miles from Round Top proper
Round Top
9.6 out of 10, Exceptional, (27 reviews)
"This is our 3rd time staying with this host for the fall antique show and have had a pleasant stay each time. "
United States
Shawna M.
The price is ￥21,518
￥33,759 total
includes taxes & fees
Mar 31 - Apr 1
Elm Grove Camper- Less than 3 miles from Round Top proper
Dining

The White Magnolia Cottage

The White Magnolia Cottage
Round Top
9.8 out of 10, Exceptional, (59 reviews)
"Great location for the Round Top Antiques Fair. Stayed only for a night but enjoyed our stay, hopefully will be back again! "
United States
Hannah M.
The price is ￥28,690
￥33,918 total
includes taxes & fees
Mar 30 - Mar 31
The White Magnolia Cottage
Terrace/patio

The Elf's Aerie, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire

The Elf's Aerie, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (19 reviews)
"We had a great time in this treehouse."
United States
Tandy S.
The price is ￥18,967
￥33,945 total
includes taxes & fees
Mar 29 - Mar 30
The Elf's Aerie, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire
Dining

Charming Cottage, 5 Minutes to Round Top!

Charming Cottage, 5 Minutes to Round Top!
Round Top
8.4 out of 10, Very Good, (5 reviews)
"Amenities were plentiful."
United States
Karen G.
The price is ￥15,939
￥30,762 total
includes taxes & fees
Apr 6 - Apr 7
Charming Cottage, 5 Minutes to Round Top!
Terrace/patio

Enchanting Casita, 5 minutes to Round Top!

Enchanting Casita, 5 minutes to Round Top!
Fayette County
9.8 out of 10, Exceptional, (69 reviews)
"My daughter and I loved staying at Enchanting Casita! Such a cute little cottage and great location! Perfect place to relax after a long day of shopping in Round Top."
United States
Michelle L.
The price is ￥17,533
￥32,563 total
includes taxes & fees
Apr 9 - Apr 10
Enchanting Casita, 5 minutes to Round Top!
Exterior

Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting
La Grange
10.0 out of 10, Exceptional, (108 reviews)
"Clean, spacious, perfect for our needs. Always enjoy staying here. "
United States
Belinda A.
The price is ￥23,669
￥37,155 total
includes taxes & fees
Apr 1 - Apr 2
Charming & Cozy Victorian in Quiet Residential Setting
Exterior

Lakefront Charm: Your Perfect Getaway in Round Top

Lakefront Charm: Your Perfect Getaway in Round Top
Fayette County
8.2 out of 10, Very Good, (11 reviews)
"Great property, will stay again. "
United States
Jerry A.
The price is ￥15,939
￥39,369 total
includes taxes & fees
Apr 9 - Apr 10
Lakefront Charm: Your Perfect Getaway in Round Top
Outdoor dining

Premium Lakefront Cabin #1: The Armadillo (Austin)

Premium Lakefront Cabin #1: The Armadillo (Austin)
Bastrop
The price is ￥28,228
￥55,165 total
includes taxes & fees
Apr 8 - Apr 9
Premium Lakefront Cabin #1: The Armadillo (Austin)
Exterior

Round Top Refuge Guest House

Round Top Refuge Guest House
La Grange
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful light and bright place to stay near RoundTop!!"
United States
Jennifer S.
The price is ￥27,256
￥51,365 total
includes taxes & fees
Apr 2 - Apr 3
Round Top Refuge Guest House
Smart TV, books

Spacious MCM home 2 minutes from downtown, Pet-Friendly!

Spacious MCM home 2 minutes from downtown, Pet-Friendly!
Smithville
9.6 out of 10, Exceptional, (15 reviews)
"We will absolutely stay here every time we're in the Austin area."
United States
Catherine K.
The price is ￥22,713
￥53,761 total
includes taxes & fees
Mar 30 - Mar 31
Spacious MCM home 2 minutes from downtown, Pet-Friendly!
Property grounds

Dodo's Place on 22 acres outside of Smithville, TX

Dodo's Place on 22 acres outside of Smithville, TX
Smithville
10.0 out of 10, Exceptional, (2 reviews)
"The host was great it cozy and peaceful would definitely stay here again when I am in the area"
United States
Cutter H.
The price is ￥15,811
￥28,395 total
includes taxes & fees
Mar 31 - Apr 1
Dodo's Place on 22 acres outside of Smithville, TX
Property grounds

The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire

The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (225 reviews)
"Well equipped, supplied and tastefully decorated. "
Singapore
William H.
The price is ￥21,836
￥37,506 total
includes taxes & fees
Apr 1 - Apr 2
The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire
Smart TV, DVD player, books, stereo

Lost Pines Lake House near Bastrop State Park and Buescher State Park..

Lost Pines Lake House near Bastrop State Park and Buescher State Park..
Smithville
9.2 out of 10, Wonderful, (35 reviews)
"We had very good and clean and comfortable accommodations. "
United States
Peter W.
The price is ￥17,071
￥31,411 total
includes taxes & fees
Apr 2 - Apr 3
Lost Pines Lake House near Bastrop State Park and Buescher State Park..
Living area

Round Top Refuge Main House

Round Top Refuge Main House
La Grange
10.0 out of 10, Exceptional, (3 reviews)
"Very Clean, Amazing Host, Wonderful location! Would definitely stay again!!"
United States
Colby W.
The price is ￥25,502
￥48,072 total
includes taxes & fees
Apr 20 - Apr 21
Round Top Refuge Main House
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

Super 8 by Wyndham Giddings

Super 8 by Wyndham Giddings

8/10 Good
"This property needs attention to cleanliness. There was fecal matter on the outside of the toilet bowl and toilet paper roll. There was broken amenities and hardware in the bathroom. Having to physically keep the toilet seat up while in use. We purchased room spray and Lysol to cover up the bathroom smells. The Front Desk was willing to adjust the rate, however we booked through this app so he couldn’t help with that. We made them aware of all of our concerns. "
Gaynell Piper 1-night trip
Posted 2 hours ago
Super 8 by Wyndham Giddings

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we give you a choice of vacation rentals near popular sights in Winchester, or you can select a more remote option if you want a relaxing place to stay.

What's the top vacation rental in Winchester?

Escape to Giddings - Charming 2-Bedroom Vacation Home: You might want to consider this vacation rental near Winchester, which is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Winchester?

Explore the area and family-friendly sights such as Jersey Barnyard, or get out into nature at a spot like Tejas Lake. In the larger area, you’ll find Bluff Creek Ranch and Buescher State Park.

What’s a vacation rental in Winchester like?

Vacation rentals are private properties where you can stay for several days or longer in Winchester. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for families.