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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Winchester vacation rentals

A compact, rustic cabin interior with a loft bedroom, a dining area with a table set for two, and a TV mounted on the wall.

1. Dodo's Place - Tiny Home on 22 Acres

Dodo's Place - Tiny Home on 22 Acres
Smithville
10.0 out of 10, Exceptional, (10 reviews)
"Loved the place perfect for its location to the bike park. Will be staying here again!!!"
United States
Law
$168 nightly
The price is $178
Nov 16 - Nov 17
Total with taxes and fees
Dodo's Place - Tiny Home on 22 Acres
A cabin with a deck, outdoor seating, and a view of a forest.

2. Cozy Studio Cottage on 22 Acres

Cozy Studio Cottage on 22 Acres
Smithville
9.2 out of 10, Wonderful, (7 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.
$139 nightly
The price is $146
Nov 11 - Nov 12
Total with taxes and fees
Cozy Studio Cottage on 22 Acres
A view of a lake with surrounding greenery and a clear sky.

3. Cozy Cottage With a View in La Grange

Cozy Cottage With a View in La Grange
La Grange
10.0 out of 10, Exceptional, (22 reviews)
"Megan is a wonderful host, we enjoyed our stay!"
United States
Leeann
$160 nightly
The price is $169
Nov 10 - Nov 11
Total with taxes and fees
Cozy Cottage With a View in La Grange
A historic building with a symmetrical facade, arched windows, and a central entrance with a balcony.

4. Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting
La Grange
10.0 out of 10, Exceptional, (118 reviews)
"One of our favorite places to stay!"
United States
Glenn R.
$201 nightly
The price is $212
Nov 15 - Nov 16
Total with taxes and fees
Charming & Cozy Victorian in Quiet Residential Setting
A campfire with a picnic table nearby, surrounded by trees and a body of water.

5. 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
$147 nightly
The price is $166
Nov 9 - Nov 10
Total with taxes and fees
Romance Glamping | Pup Paradise | Near River | ADA
A living room with a sofa, a bed, a dining area, and a kitchen.

6. 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, (41 reviews)
"Extremely clean and very nicely furnished with unique artwork."
United States
Richard
$213 nightly
The price is $225
Nov 16 - Nov 17
Total with taxes and fees
Lost Pines Lake House near Bastrop State Park and Buescher State Park..
A wooden playground with a slide, climbing area, and swings.

7. 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, (23 reviews)
"We enjoyed the quiet and no wi-fri.....the phone worked fine, don't like them either. Will stay there again if I ever get out to that area in Texas again. Thank you."
United States
James
$259 nightly
The price is $290
Nov 9 - Nov 10
Total with taxes and fees
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
A compact RV interior with a kitchenette, a seating area, and a small dining table.

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

Riverside Romance/Luxury RV/Starry Skies & S'mores
Smithville
10.0 out of 10, Exceptional, (73 reviews)
"Very cozy cute little get away place. Very much so enjoyed our stay and the host was on top of always responding to any message fast and prompt."
United States
Renee H.
$142 nightly
The price is $160
Nov 9 - Nov 10
Total with taxes and fees
Riverside Romance/Luxury RV/Starry Skies & S'mores
A wooden staircase with natural tree branches integrated into the structure, leading to a covered area.

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

The Hobbit's Nest Treehouse, A Dog-friendly Treehouse in the Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (239 reviews)
"Fun property, enjoyed our stay very much"
United States
Jessica H.
$176 nightly
The price is $198
Dec 3 - Dec 4
Total with taxes and fees
The Hobbit's Nest Treehouse, A Dog-friendly Treehouse in the Lost Pines Shire
A two-story house with a covered patio area, outdoor seating, and a dog.

10. Round Top Refuge Guest House

Round Top Refuge Guest House
La Grange
10.0 out of 10, Exceptional, (12 reviews)
"Fabulous stay, can’t wait to come back!"
United States
Karin C.
$362 nightly
The price is $382
Nov 10 - Nov 11
Total with taxes and fees
Round Top Refuge Guest House
A covered outdoor area with a gravel floor, surrounded by trees and a body of water.

11. 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
$82 nightly
The price is $86
Nov 8 - Nov 9
Total with taxes and fees
Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse
A modern kitchen with a central island, pendant lighting, and a dining area with a wooden table and chairs.

12. La Grange Modern Farmhouse, breathtaking views!

La Grange Modern Farmhouse, breathtaking views!
La Grange
10.0 out of 10, Exceptional, (11 reviews)
"Awesome house, great communication. Book here for a fun escape to the country!"
United States
Sean & Corrie R.
$635 nightly
The price is $655
Nov 8 - Nov 9
Total with taxes and fees
La Grange Modern Farmhouse, breathtaking views!
A bedroom with a sloped ceiling, a chandelier, a bed with a wooden headboard, a patterned rug, and a window with a view.

13. Swiss Alp Texas Cabin

Swiss Alp Texas Cabin
Schulenburg
10.0 out of 10, Exceptional, (12 reviews)
"The place was lovely and communication with the host was so quick and helpful! Highly recommend!"
United States
Tracey C.
$159 nightly
The price is $168
Nov 8 - Nov 9
Total with taxes and fees
Swiss Alp Texas Cabin
A wooden deck with a view of a forested area.

14. The Cactus House - Fenced Yard + Dogs Stay Free

The Cactus House - Fenced Yard + Dogs Stay Free
Paige
10.0 out of 10, Exceptional, (237 reviews)
"Fantastic little get away spot. Nice area to relax and within very close drive by range to either good BBQ or a distillery and brewery. Would definitely stay again."
United States
Josh S.
$204 nightly
The price is $229
Nov 8 - Nov 9
Total with taxes and fees
The Cactus House - Fenced Yard + Dogs Stay Free
A spacious living room with a fireplace, a kitchen in the background, and a dining area with a table and chairs.

15. Walk to Lake + Stock Tank Pool + Fire Pit

Walk to Lake + Stock Tank Pool + Fire Pit
Bastrop
10.0 out of 10, Exceptional, (129 reviews)
"Awesome place to stay! Being from south Texas it sure was a change in scenery!"
United States
John P.
$356 nightly
The price is $376
Nov 8 - Nov 9
Total with taxes and fees
Walk to Lake + Stock Tank Pool + Fire Pit
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, (70 reviews)
"Beautiful cottage, it was perfect for us!"
United States
Amy
$259 nightly
The price is $273
Nov 10 - Nov 11
Total with taxes and fees
The White Magnolia Cottage
A modern kitchen with white cabinets, a wooden countertop, and a central island. There are two pendant lights and a large window providing a view of the outdoors.

17. Modern Retreat in the Pine Forest of Bastrop, minutes from Space X

Modern Retreat in the Pine Forest of Bastrop, minutes from Space X
Bastrop
10.0 out of 10, Exceptional, (13 reviews)
"We loved our stay. The accommodations were very comfortable and clean in a quiet neighborhood setting."
United States
Diana d.
$323 nightly
The price is $341
Nov 16 - Nov 17
Total with taxes and fees
Modern Retreat in the Pine Forest of Bastrop, minutes from Space X
A covered porch with a wicker sofa, hanging plants, and a view of the yard.

18. Charming 3-bedroom house with AC in La Grange with Wrap around porches.

Charming 3-bedroom house with AC in La Grange with Wrap around porches.
La Grange
10.0 out of 10, Exceptional, (9 reviews)
"We always LOVE staying here, Mary is always so welcoming and accommodating. The home is beautiful and feels like our home away from home. The hot tub and patios wrap around are perfect throughout the day."
United States
Aundrea G.
$464 nightly
The price is $491
Nov 16 - Nov 17
Total with taxes and fees
Charming 3-bedroom house with AC in La Grange with Wrap around porches.
A wooden deck with a railing, a bench, and a table with chairs.

19. Lost Pines Cottage - Fenced Yard + Dogs Stay Free

Lost Pines Cottage - Fenced Yard + Dogs Stay Free
Paige
10.0 out of 10, Exceptional, (405 reviews)
"Amazing location and just a great cabin. "
United States
Sean H.
$176 nightly
The price is $198
Nov 15 - Nov 16
Total with taxes and fees
Lost Pines Cottage - Fenced Yard + Dogs Stay Free
A modern kitchen with a large island, stainless steel appliances, pendant lighting, and a stone fireplace.

20. Windy Hill Retreat | Modern Farmhouse with Views, Cowboy Pool & Firepit

Windy Hill Retreat | Modern Farmhouse with Views, Cowboy Pool & Firepit
La Grange
10.0 out of 10, Exceptional, (11 reviews)
"This house was perfect! We had a lovely Girl’s Stay and enjoyed the clean, comfy home and Cowboy Pool too! The coffee bar and kitchen were the best I’ve seen! I highly recommend this house!!"
United States
Traci J.
$555 nightly
The price is $570
Nov 8 - Nov 9
Total with taxes and fees
Windy Hill Retreat | Modern Farmhouse with Views, Cowboy Pool & Firepit
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
"Older hotel, room clean, commode seat was broken"
Jennifer 1-night trip
Posted 14 hours ago
Super 8 by Wyndham Giddings

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 $160 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 Tejas Lake. In the larger area, you’ll find Bluff Creek Ranch and Texas Wendish Heritage Museum.

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.