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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Winchester vacation rentals

Exterior

1. Adorable Guest Cabin In The Woods

Adorable Guest Cabin In The Woods
La Grange
9.8 out of 10, Exceptional, (81 reviews)
"Wonderful location, property was clean, very cozy"
United States
Billie P.
$129 nightly
The price is $136
Aug 19 - Aug 20
Total with taxes and fees
Adorable Guest Cabin In The Woods
Interior

2. Pinehaven Luxury Glamping

Pinehaven Luxury Glamping
La Grange
10.0 out of 10, Exceptional, (65 reviews)
"Beautiful property and the host was fast to respond to a minor A/C issue that came up."
United States
Micah P.
$205 nightly
The price is $216
Aug 23 - Aug 24
Total with taxes and fees
Pinehaven Luxury Glamping
Property grounds

3. Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse

Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse
Smithville
$67 nightly
The price is $70
Aug 16 - Aug 17
Total with taxes and fees
Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse
Property grounds

4. 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
$140 nightly
The price is $147
Aug 16 - Aug 17
Total with taxes and fees
Cozy Cottage With a View in La Grange
Spa

5. 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
8.8 out of 10, Excellent, (5 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
Sep 5 - Sep 6
Total with taxes and fees
Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
Spa

6. 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, (6 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
Sep 1 - Sep 2
Total with taxes and fees
Dodo's Place on 22 acres outside of Smithville, TX
Interior

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

Riverside Romance/Luxury RV/Starry Skies & S'mores
Smithville
10.0 out of 10, Exceptional, (69 reviews)
"Great riverside spot. Very clean and comfortable."
United States
Wini H.
$153 nightly
The price is $171
Aug 17 - Aug 18
Total with taxes and fees
Riverside Romance/Luxury RV/Starry Skies & S'mores
Exterior

8. Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting
La Grange
10.0 out of 10, Exceptional, (113 reviews)
"One of our favorite places to stay!"
United States
Glenn R.
$190 nightly
The price is $199
Aug 20 - Aug 21
Total with taxes and fees
Charming & Cozy Victorian in Quiet Residential Setting
Property grounds

9. 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.
$146 nightly
The price is $163
Aug 16 - Aug 17
Total with taxes and fees
Romance Glamping | Pup Paradise | Near River | ADA
1 bedroom, WiFi, bed sheets

10. Swiss Alp Texas Cabin

Swiss Alp Texas Cabin
Schulenburg
9.8 out of 10, Exceptional, (10 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
Aug 16 - Aug 17
Total with taxes and fees
Swiss Alp Texas Cabin
Smart TV, DVD player, books, stereo

11. 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, (40 reviews)
"It was quiet and secluded. We were able to sit back and relax after hiking all day. I would rent this house again."
United States
Theresa
$225 nightly
The price is $237
Aug 20 - Aug 21
Total with taxes and fees
Lost Pines Lake House near Bastrop State Park and Buescher State Park..
Children's area

12. 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)
"A wonderful place to stay while we attended the AKC hunt trials. Dry clean & had everything we needed. We also spent a relaxing, rainy evening watching a movie."
United States
Jacque H.
$286 nightly
The price is $319
Aug 16 - Aug 17
Total with taxes and fees
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
Exterior

13. 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.
$343 nightly
The price is $361
Aug 14 - Aug 15
Total with taxes and fees
Round Top Refuge Guest House
Terrace/patio

14. Steps away from the sweet LaGrange downtown square

Steps away from the sweet LaGrange downtown square
La Grange
9.4 out of 10, Exceptional, (11 reviews)
"A great place to stay. Very hospitable and enjoyed our stay!"
United States
William A.
$633 nightly
The price is $658
Aug 14 - Aug 15
Total with taxes and fees
Steps away from the sweet LaGrange downtown square
Lobby

15. 2 Queen Beds|Nsmk,Kitchen

2 Queen Beds|Nsmk,Kitchen
Giddings TX
10.0 out of 10, Exceptional, (51 reviews)
$143 nightly
The price is $162
Aug 14 - Aug 15
Total with taxes and fees
2 Queen Beds|Nsmk,Kitchen
1 bedroom, desk, WiFi, bed sheets

16. Enchanting Casita, 5 minutes to Round Top!

Enchanting Casita, 5 minutes to Round Top!
Fayette County
9.4 out of 10, Exceptional, (76 reviews)
"location is great and clean"
United States
Jeff H.
$220 nightly
The price is $225
Aug 20 - Aug 21
Total with taxes and fees
Enchanting Casita, 5 minutes to Round Top!
Property grounds

17. 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, (237 reviews)
"Beautiful and peaceful little treehouse with all of the LOTR decor you would want. The owners thought of everything you could need and it was very comfortable."
United States
Amy P.
$199 nightly
The price is $222
Aug 19 - Aug 20
Total with taxes and fees
The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire
Living area

18. 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
10.0 out of 10, Exceptional, (2 reviews)
"really liked the area. the space was nice and cozy, very clean."
United States
sara
$144 nightly
The price is $152
Sep 1 - Sep 2
Total with taxes and fees
Cozy 1-bedroom cabin in lovely Bastrop- stay a weekend or longer
Terrace/patio

19. 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
9.8 out of 10, Exceptional, (10 reviews)
"We had a great time and everything we needed was available. "
United States
Jenna H.
$181 nightly
The price is $201
Aug 16 - Aug 17
Total with taxes and fees
The Elf's Aerie, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire
Dining

20. Charming Cottage, 5 Minutes to Round Top!

Charming Cottage, 5 Minutes to Round Top!
Round Top
8.4 out of 10, Very Good, (6 reviews)
"Amenities were plentiful."
United States
Karen G.
$236 nightly
The price is $242
Aug 14 - Aug 15
Total with taxes and fees
Charming Cottage, 5 Minutes to Round Top!
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

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

10/10 Excellent
"I love hobbit holes and this place hit the spot! We had been staying in SPI and were heading back early to split the drive home into 2 days. The tree house was available for the one night we needed! Check in was easy, the space was clean, bed was comfortable, and we enjoyed the night playing cards. Lately when we've been trying to find places that are unique - very happy we found this place!"
Valerie Sean S. 1-night trip
Posted 2 days ago
The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire

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 $136 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?

Walk to Lake + Stock Tank Pool + Fire Pit: Visitors like this Winchester vacation home rental. It is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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 Mid Town Lee Smith Park. In the larger area, you’ll find Bluff Creek Ranch and The Old Fayette County Jail.

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.