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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
The price is CA $52
CA $99 total
includes taxes & fees
Sep 29 - Sep 30
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.
The price is CA $108
CA $218 total
includes taxes & fees
Sep 29 - Sep 30
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
The price is CA $146
CA $258 total
includes taxes & fees
Sep 29 - Sep 30
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
The price is CA $140
CA $222 total
includes taxes & fees
Oct 5 - Oct 6
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.
The price is CA $99
CA $236 total
includes taxes & fees
Sep 30 - Oct 1
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.
The price is CA $172
CA $281 total
includes taxes & fees
Oct 4 - Oct 5
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
The price is CA $151
CA $331 total
includes taxes & fees
Oct 5 - Oct 6
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
The price is CA $137
CA $279 total
includes taxes & fees
Oct 5 - Oct 6
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.
The price is CA $209
CA $518 total
includes taxes & fees
Oct 5 - Oct 6
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.
The price is CA $209
CA $515 total
includes taxes & fees
Oct 5 - Oct 6
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.
The price is CA $159
CA $234 total
includes taxes & fees
Sep 29 - Sep 30
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.
The price is CA $198
CA $433 total
includes taxes & fees
Sep 30 - Oct 1
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.
The price is CA $223
CA $283 total
includes taxes & fees
Sep 29 - Sep 30
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.
The price is CA $263
CA $663 total
includes taxes & fees
Oct 5 - Oct 6
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
The price is CA $223
CA $283 total
includes taxes & fees
Sep 29 - Sep 30
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
The price is CA $255
CA $302 total
includes taxes & fees
Sep 29 - Sep 30
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 traveller
The price is CA $200
CA $226 total
includes taxes & fees
Sep 29 - Sep 30
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.
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.
The price is CA $314
CA $546 total
includes taxes & fees
Sep 30 - Oct 1
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.
The price is CA $236
CA $299 total
includes taxes & fees
Sep 29 - Sep 30
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 7 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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester vacation rentals we have selected for you start as low as CA $236 per night. Entering your travel dates in the search wizard 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.