Default HTG hotel image

Winchester Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

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, (77 reviews)
"Wonderful location, property was clean, very cozy"
United States
Billie P.
$129 nightly
The price is $136
Jun 29 - Jun 30
Total with taxes and fees
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, (15 reviews)
"We enjoyed our stay! This cottage is perfect for a getaway or planned layover between San Antonio and Austin. The vibe was great."
Canada
Paul
$142 nightly
The price is $149
Jul 6 - Jul 7
Total with taxes and fees
Cozy Cottage With a View in La Grange
Interior

Pinehaven Luxury Glamping

Pinehaven Luxury Glamping
La Grange
10.0 out of 10, Exceptional, (63 reviews)
"We enjoyed our stay. Very Peaceful. Everything was great. "
United States
Anonymous traveler
$202 nightly
The price is $213
Jul 12 - Jul 13
Total with taxes and fees
Pinehaven Luxury Glamping
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.
$158 nightly
The price is $166
Jun 29 - Jun 30
Total with taxes and fees
Swiss Alp Texas Cabin
Spa

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, (5 reviews)
"Loved the place perfect for its location to the bike park. Will be staying here again!!!"
United States
Law
$193 nightly
The price is $203
Jul 6 - Jul 7
Total with taxes and fees
Dodo's Place on 22 acres outside of Smithville, TX
Exterior

Round Top Refuge Guest House

Round Top Refuge Guest House
La Grange
9.8 out of 10, Exceptional, (10 reviews)
"Fabulous stay, can’t wait to come back!"
United States
Karin C.
$353 nightly
The price is $371
Jul 6 - Jul 7
Total with taxes and fees
Round Top Refuge Guest House
Living area

Cozy 1-bedroom cabin in lovely Bastrop- stay a weekend or longer

Cozy 1-bedroom cabin in lovely Bastrop- stay a weekend or longer
Bastrop
$144 nightly
The price is $151
Jul 28 - Jul 29
Total with taxes and fees
Cozy 1-bedroom cabin in lovely Bastrop- stay a weekend or longer
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
10.0 out of 10, Exceptional, (22 reviews)
"This was the perfect getaway for our family to truly disconnect and unwind. The location was ideal for visiting the Sherwood Forest Faire, making our trip even more special. We loved getting to see the sheep, lambs, and chickens, which was such a fun experience for our 2-year-old. It was peaceful, family-friendly, and exactly what we were looking for. We would absolutely stay here again!"
United States
Jordyn D.
$282 nightly
The price is $315
Jul 1 - Jul 2
Total with taxes and fees
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
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.
$202 nightly
The price is $213
Jun 29 - Jun 30
Total with taxes and fees
Elm Grove Camper- Less than 3 miles from Round Top proper
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.
$244 nightly
The price is $250
Jun 29 - Jun 30
Total with taxes and fees
Charming Cottage, 5 Minutes to Round Top!
Dining

The White Magnolia Cottage

The White Magnolia Cottage
Round Top
9.8 out of 10, Exceptional, (60 reviews)
"Beautiful cottage, it was perfect for us!"
United States
Amy
$202 nightly
The price is $213
Jun 29 - Jun 30
Total with taxes and fees
The White Magnolia Cottage
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, (38 reviews)
"Had a great stay during the Christmas holidays to visit the Observatory. Good location."
United States
Albert C.
$223 nightly
The price is $235
Jul 6 - Jul 7
Total with taxes and fees
Lost Pines Lake House near Bastrop State Park and Buescher State Park..
Spa

Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat

Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
Smithville
9.6 out of 10, Exceptional, (4 reviews)
"I was out here on a work trip - great location for a quick trip. Just the correct size for one person. And the goats are amazing!!!"
United States
Jim C.
$147 nightly
The price is $154
Jul 2 - Jul 3
Total with taxes and fees
Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
1 bedroom, desk, WiFi, bed sheets

Enchanting Casita, 5 minutes to Round Top!

Enchanting Casita, 5 minutes to Round Top!
Fayette County
9.4 out of 10, Exceptional, (76 reviews)
"Very cute! Easy access to town and an easy stay"
United States
Blah S.
$257 nightly
The price is $263
Jun 29 - Jun 30
Total with taxes and fees
Enchanting Casita, 5 minutes to Round Top!
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, (235 reviews)
"It was more Magical than described, prepare to be amazed."
United States
Renee
$210 nightly
The price is $234
Jun 30 - Jul 1
Total with taxes and fees
The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire
Interior

Riverside Romance/Luxury RV/Starry Skies & S'mores

Riverside Romance/Luxury RV/Starry Skies & S'mores
Smithville
10.0 out of 10, Exceptional, (66 reviews)
"Great riverside spot. Very clean and comfortable."
United States
Wini H.
$161 nightly
The price is $180
Jun 29 - Jun 30
Total with taxes and fees
Riverside Romance/Luxury RV/Starry Skies & S'mores
Exterior

Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting
La Grange
10.0 out of 10, Exceptional, (110 reviews)
"One of our favorite places to stay!"
United States
Glenn R.
$222 nightly
The price is $233
Jun 29 - Jun 30
Total with taxes and fees
Charming & Cozy Victorian in Quiet Residential Setting
Property grounds

Romance Glamping | Pup Paradise | Near River | ADA

Romance Glamping | Pup Paradise | Near River | ADA
Smithville
10.0 out of 10, Exceptional, (4 reviews)
"We had an amazing time! We had everything we needed and more! It was nice and peaceful. A nice getaway from the city life. Being able to watch birds come up to the window was just awesome. Would love to stay again!"
United States
Cassie R.
$181 nightly
The price is $203
Jul 19 - Jul 20
Total with taxes and fees
Romance Glamping | Pup Paradise | Near River | ADA
Outdoor dining

Premium Lakefront Cabin #1: The Armadillo (Austin)

Premium Lakefront Cabin #1: The Armadillo (Austin)
Bastrop
$386 nightly
The price is $414
Jul 16 - Jul 17
Total with taxes and fees
Premium Lakefront Cabin #1: The Armadillo (Austin)
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Best Western La Grange Inn & Suites

Best Western La Grange Inn & Suites

10/10 Excellent
"I had a different circumstance that required me to go down there a day earlier...I tried through Expedia to change my reservation but was not successful. I called the hotel directly and they were able to assist me so I ended up staying a day earlier and kept my reservation for the original night stay. Hope and the crew were amazingly understanding and helpful. I did not catch the name of the woman who made the breakfasts but when my kid came down, she checked in on her and she made sure she had what she needed and asked if we needed anything else. I mean great customer service there and we've been going and staying there for the past 12 years. It is literally right up the road from the summer camp that we've been going to, it's about 45-minute drive from brenham to go get ice cream, and roughly about 20-25 minutes to round top. So it's a good centrally located hotel."
Kristi 1-night trip
Posted 2 days ago
Best Western La Grange Inn & Suites

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $180 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Waterfront Smithville River House: You might want to consider this vacation home rental near Winchester, which is located on the waterfront and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 Boat 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.