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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Winchester vacation rentals

A cabin with a deck, outdoor seating, and a view of a forest.

1. 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 15 - Nov 16
Total with taxes and fees
Cozy Studio Cottage on 22 Acres
A covered outdoor area with a gravel floor, surrounded by trees and a body of water.

2. 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 13 - Nov 14
Total with taxes and fees
Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse
A wooden deck with a metal roof, surrounded by trees.

3. 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
$166 nightly
The price is $176
Nov 16 - Nov 17
Total with taxes and fees
Dodo's Place - Tiny Home on 22 Acres
An outdoor patio with a fire pit, picnic table, and seating area.

4. 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.
$146 nightly
The price is $164
Nov 16 - Nov 17
Total with taxes and fees
Riverside Romance/Luxury RV/Starry Skies & S'mores
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
$157 nightly
The price is $177
Dec 1 - Dec 2
Total with taxes and fees
Romance Glamping | Pup Paradise | Near River | ADA
A view of a lake with surrounding greenery and a clear sky.

6. 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
$163 nightly
The price is $172
Nov 19 - Nov 20
Total with taxes and fees
Cozy Cottage With a View in La Grange
A covered outdoor seating area with wooden furniture, string lights, and a view of the outdoors.

7. Indoor-Outdoor Escape, Screened Porch, Starlink

Indoor-Outdoor Escape, Screened Porch, Starlink
Paige
$237 nightly
The price is $237
Nov 16 - Nov 17
Total with taxes and fees
Indoor-Outdoor Escape, Screened Porch, Starlink
A wooden cabin with a porch, string lights, and a hanging chair.

8. Romantic Getaway, King Bed, Nature!

Romantic Getaway, King Bed, Nature!
Paige
$249 nightly
The price is $249
Dec 8 - Dec 9
Total with taxes and fees
Romantic Getaway, King Bed, Nature!
A backyard with a brick pathway, a swing set, and chickens.

9. 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 19 - Nov 20
Total with taxes and fees
Lost Pines Lake House near Bastrop State Park and Buescher State Park..
A historic building with a symmetrical facade, arched windows, and a central entrance with a balcony.

10. Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting
La Grange
10.0 out of 10, Exceptional, (118 reviews)
"I would definitely stay here again!"
United States
Anne Z.
$201 nightly
The price is $212
Nov 15 - Nov 16
Total with taxes and fees
Charming & Cozy Victorian in Quiet Residential Setting
A beige door with a 'Restrooms' sign, a keypad lock, and a window above it.

11. 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.
$160 nightly
The price is $169
Nov 15 - Nov 16
Total with taxes and fees
Swiss Alp Texas Cabin
A wooden treehouse with a circular window and a wooden staircase.

12. 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.
$182 nightly
The price is $204
Dec 8 - Dec 9
Total with taxes and fees
The Hobbit's Nest Treehouse, A Dog-friendly Treehouse in the Lost Pines Shire
A metal gate with the words "Blessing Ranch" engraved on it.

13. 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 15 - Nov 16
Total with taxes and fees
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
A wooden cabin with a metal roof, a porch, and a fenced yard.

14. 10m to Roadhouse Bastrop & Riverwalk w/Patio - WiFi + Outdoor furniture

10m to Roadhouse Bastrop & Riverwalk w/Patio - WiFi + Outdoor furniture
Bastrop
$137 nightly
The price is $145
Nov 15 - Nov 16
Total with taxes and fees
10m to Roadhouse Bastrop & Riverwalk w/Patio - WiFi + Outdoor furniture
A wooden cabin with a balcony, a lantern, and a view of trees and a clear sky.

15. Elf's Aerie Treehouse - Outdoor Shower + Deck

Elf's Aerie Treehouse - Outdoor Shower + Deck
Paige
10.0 out of 10, Exceptional, (14 reviews)
"This was such an amazing stay! We will be back soon!"
United States
Isabel G.
$182 nightly
The price is $204
Nov 18 - Nov 19
Total with taxes and fees
Elf's Aerie Treehouse - Outdoor Shower + Deck
A campfire surrounded by chairs in a forested area with string lights.

16. 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.
$343 nightly
The price is $361
Nov 16 - Nov 17
Total with taxes and fees
Walk to Lake + Stock Tank Pool + Fire Pit
A hotel room with two beds, a desk, a TV, and a window with curtains.

17. 2 Queen Beds|Nsmk,Kitchen

2 Queen Beds|Nsmk,Kitchen
Giddings TX
10.0 out of 10, Exceptional, (360 reviews)
"Comfy stay and parking made my trip easy!"
United States
Anonymous traveler
$111 nightly
The price is $125
Nov 22 - Nov 23
Total with taxes and fees
2 Queen Beds|Nsmk,Kitchen
A wooden deck with a railing, a bench, and a table with chairs.

18. 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.
$174 nightly
The price is $196
Nov 16 - Nov 17
Total with taxes and fees
Lost Pines Cottage - Fenced Yard + Dogs Stay Free
A wooden deck with a table and chairs, surrounded by a wooden railing, overlooking a wooded area.

19. 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.
$197 nightly
The price is $222
Nov 16 - Nov 17
Total with taxes and fees
The Cactus House - Fenced Yard + Dogs Stay Free
A two-story house with a covered patio area, outdoor seating, and a dog.

20. 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.
$369 nightly
The price is $389
Dec 8 - Dec 9
Total with taxes and fees
Round Top Refuge Guest House
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

Best Western La Grange Inn & Suites

Best Western La Grange Inn & Suites

10/10 Excellent
"Wonderful breakfast and a nice clean room."
Natalie 1-night trip
Posted 18 hours 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 $164 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.