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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winchester vacation rentals

A covered outdoor area with a gravel floor, surrounded by trees and a body of water.

1. 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
Sep 29 - Sep 30
Total with taxes and fees
Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse
A hot tub with a wooden deck, a metal roof, and a view of a natural landscape.

2. 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
9.0 out of 10, Wonderful, (6 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 29 - Sep 30
Total with taxes and fees
Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
A hot tub with a wooden deck, a metal roof, and a view of a natural landscape.

3. 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, (7 reviews)
"Loved the place perfect for its location to the bike park. Will be staying here again!!!"
United States
Law
$174 nightly
The price is $183
Sep 29 - Sep 30
Total with taxes and fees
Dodo's Place on 22 acres outside of Smithville, TX
A view of a lake with surrounding greenery and a clear sky.

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, (17 reviews)
"Megan is a wonderful host, we enjoyed our stay!"
United States
Leeann
$149 nightly
The price is $157
Oct 5 - Oct 6
Total with taxes and fees
Cozy Cottage With a View in La Grange
A compact RV interior with a kitchenette, a seating area, and a small dining table.

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

Riverside Romance/Luxury RV/Starry Skies & S'mores
Smithville
10.0 out of 10, Exceptional, (72 reviews)
"Very peaceful and clean"
United States
Lauren S.
$149 nightly
The price is $167
Sep 30 - Oct 1
Total with taxes and fees
Riverside Romance/Luxury RV/Starry Skies & S'mores
A historic building with a symmetrical facade, arched windows, and a central entrance with a balcony.

6. Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting
La Grange
10.0 out of 10, Exceptional, (115 reviews)
"One of our favorite places to stay!"
United States
Glenn R.
$187 nightly
The price is $196
Oct 4 - Oct 5
Total with taxes and fees
Charming & Cozy Victorian in Quiet Residential Setting
A living room with a sofa, a bed, a dining area, and a kitchen.

7. 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
$217 nightly
The price is $229
Oct 5 - Oct 6
Total with taxes and fees
Lost Pines Lake House near Bastrop State Park and Buescher State Park..
A campfire with a picnic table nearby, surrounded by trees and a body of water.

8. Romance Glamping | Pup Paradise | Near River | ADA

Romance Glamping | Pup Paradise | Near River | ADA
Smithville
10.0 out of 10, Exceptional, (4 reviews)
"The property is beautiful and the RV is very clean. There are tons of amenities. We enjoyed watching the cardinals and humming birds!"
United States
Kimberly
$169 nightly
The price is $189
Oct 6 - Oct 7
Total with taxes and fees
Romance Glamping | Pup Paradise | Near River | ADA
A living room with a sofa, a round coffee table, and a lamp.

9. The Lucy | Sweet Retreat for 2-4 Near Ice Plant

The Lucy | Sweet Retreat for 2-4 Near Ice Plant
La Grange
10.0 out of 10, Exceptional, (1 review)
"Lovely home close to round top! House was well equipped with everything we needed. Bed and sofa sleeper were very comfortable. "
United States
Erin M.
$321 nightly
The price is $351
Oct 5 - Oct 6
Total with taxes and fees
The Lucy | Sweet Retreat for 2-4 Near Ice Plant
A modern kitchen with a black sink, a coffee machine, and a dining area with wicker chairs and a round table.

10. 2nd Floor Loft Across from Ice Plant | The Otis

2nd Floor Loft Across from Ice Plant | The Otis
La Grange
10.0 out of 10, Exceptional, (6 reviews)
"stayed here with my mom, aunt and sister-in-law for a girls trip for round top! slept 4 comfortably, honestly had plenty of room. location was perfect for us, just a little over 20 min drive to the trade shows and conveniently there was a HEB practically across the street for any necessities ! would def stay here again. "
United States
Hunter L.
$321 nightly
The price is $351
Oct 5 - Oct 6
Total with taxes and fees
2nd Floor Loft Across from Ice Plant | The Otis
A bedroom with a sloped ceiling, a chandelier, a bed with a wooden headboard, a patterned rug, and a window with a view.

11. 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
Sep 29 - Sep 30
Total with taxes and fees
Swiss Alp Texas Cabin
A wooden playground with a slide, climbing area, and swings.

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.
$260 nightly
The price is $291
Sep 30 - Oct 1
Total with taxes and fees
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
A wooden cabin with a blue roof, surrounded by a wooden deck and metal railings, set in a forested area.

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

The Elf's Aerie Treehouse, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time and everything we needed was available. "
United States
Jenna H.
$178 nightly
The price is $198
Sep 29 - Sep 30
Total with taxes and fees
The Elf's Aerie Treehouse, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire
A living room with a white sofa, a grey armchair, a dining table with wicker chairs, and a small side table with a lamp.

14. Porch Swing Vibes for 4 | Francis @ Grace Inn

Porch Swing Vibes for 4 | Francis @ Grace Inn
La Grange
10.0 out of 10, Exceptional, (4 reviews)
"Awesome stay, very convenient and cute "
United States
Christie B.
$410 nightly
The price is $452
Oct 5 - Oct 6
Total with taxes and fees
Porch Swing Vibes for 4 | Francis @ Grace Inn
A wooden staircase leading to a cabin with a wooden exterior and a wooden deck.

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

The Hobbit's Nest Treehouse, A Magical Dog-friendly Treehouse in the Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (238 reviews)
"Incredibly charming one of a kind experience, kids loved the woodland details and felt like stepping on to a movie set. Excellent host communication, we felt like guests in the true sense of the word."
United States
Gavin
$178 nightly
The price is $198
Sep 29 - Sep 30
Total with taxes and fees
The Hobbit's Nest Treehouse, A Magical Dog-friendly Treehouse in the Lost Pines Shire
A dining table set with a cake, teapot, cups, and a vase of flowers.

16. The White Magnolia Cottage

The White Magnolia Cottage
Round Top
9.8 out of 10, Exceptional, (66 reviews)
"Beautiful cottage, it was perfect for us!"
United States
Amy
$200 nightly
The price is $211
Sep 29 - Sep 30
Total with taxes and fees
The White Magnolia Cottage
A reception desk with a colorful striped wall, a large number '6' sign, and a blue informational sign.

17. 2 Queen Beds|Nsmk,Kitchen

2 Queen Beds|Nsmk,Kitchen
Giddings TX
10.0 out of 10, Exceptional, (359 reviews)
"Awesome value for what we got, it was perfect for a weekend getaway!"
United States
Anonymous traveler
$141 nightly
The price is $160
Sep 29 - Sep 30
Total with taxes and fees
2 Queen Beds|Nsmk,Kitchen
A dining area with a wooden table, four wicker chairs, a chandelier, and a blue and white vase with flowers.

18. Bridal Ready + Southern Charm | The Moli

Bridal Ready + Southern Charm | The Moli
La Grange
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful place to stay. Loved the decor. Can't wait to stay again."
United States
Trisha T.
$457 nightly
The price is $504
Oct 5 - Oct 6
Total with taxes and fees
Bridal Ready + Southern Charm | The Moli
A two-story house with a covered patio area, outdoor seating, and a dog.

19. 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.
$342 nightly
The price is $361
Sep 29 - Sep 30
Total with taxes and fees
Round Top Refuge Guest House
A wooden deck with a railing, a bench, and a table with chairs.

20. The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire

The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (403 reviews)
"Amazing location and just a great cabin. "
United States
Sean H.
$187 nightly
The price is $209
Sep 29 - Sep 30
Total with taxes and fees
The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire
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

Walk to Lake + Stock Tank Pool + Fire Pit

Walk to Lake + Stock Tank Pool + Fire Pit

10/10 Excellent
"This was our second stay and it was just as good as the first. The house is tucked back in the pines and feels completely secluded. Everything was spotless and thoughtfully put together, and it's even prettier in person than in the photos. The hosts were so communicative and gracious, which made everything easy. We're planning to make this an annual trip!"
Brooke P. 2-night trip
Posted 8 hours ago
Walk to Lake + Stock Tank Pool + Fire Pit

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 $167 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 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.