Winchester Vacation Rentals

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Dec 7 - Dec 8
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Dec 8 - Dec 9
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Vacation Rentals in Winchester

Exterior
Swiss Alp Texas Cabin

Swiss Alp Texas Cabin

Schulenburg
9.8 out of 10, Exceptional, (8)
"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
Dec 9 - Dec 10
Total with taxes and fees
Swiss Alp Texas Cabin
Property grounds
Cozy Cottage With a View in La Grange

Cozy Cottage With a View in La Grange

La Grange
10.0 out of 10, Exceptional, (9)
$140 nightly
The price is $147
Dec 9 - Dec 10
Total with taxes and fees
Cozy Cottage With a View in La Grange
Private kitchen
Adorable Guest Cabin In The Woods

Adorable Guest Cabin In The Woods

La Grange
9.8 out of 10, Exceptional, (65)
"This was a great experience. The cabin was charming, clean, and easy to find. I really enjoyed staying in a quite, clean environment, watching the deer in the morning was a welcomed surprise, and it was easy to get to Round Top which was my weekend adventure. Thank you."
United States
Sherry
$129 nightly
The price is $136
Dec 9 - Dec 10
Total with taxes and fees
Adorable Guest Cabin In The Woods
Outdoor dining
Round Top Refuge Guest House

Round Top Refuge Guest House

La Grange
10.0 out of 10, Exceptional, (5)
"Great place to stay! "
United States
Natalie S.
$286 nightly
The price is $301
Dec 9 - Dec 10
Total with taxes and fees
Round Top Refuge Guest House
Exterior detail
8 Minutes from Round Top! Your Silo-Bration Destination StoneHENge Silo #2

8 Minutes from Round Top! Your Silo-Bration Destination StoneHENge Silo #2

La Grange
9.8 out of 10, Exceptional, (42)
"Absolutely amazing!!! BEYOND our expectations with the adorable atmosphere, incredibly comfortable bed & amazing outdoor space! Highly recommend!!"
United States
Kevan
$339 nightly
The price is $357
Dec 9 - Dec 10
Total with taxes and fees
8 Minutes from Round Top! Your Silo-Bration Destination StoneHENge Silo #2
Interior
Elm Grove Camper- Less than 3 miles from Round Top proper

Elm Grove Camper- Less than 3 miles from Round Top proper

Round Top
9.6 out of 10, Exceptional, (27)
"The camper fit our needs perfectly! Quiet beautiful surroundings and close to all the activities that Round Top has to offer. We will definitely be back. Ashley the host was awesome!"
United States
Karen H.
$201 nightly
The price is $212
Dec 9 - Dec 10
Total with taxes and fees
Elm Grove Camper- Less than 3 miles from Round Top proper
Terrace/patio
Pinehaven Luxury Glamping

Pinehaven Luxury Glamping

La Grange
10.0 out of 10, Exceptional, (49)
"Great location, quiet stay. "
United States
Brandon R.
$189 nightly
The price is $199
Dec 9 - Dec 10
Total with taxes and fees
Pinehaven Luxury Glamping
Fridge, microwave, oven, stovetop
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
9.8 out of 10, Exceptional, (19)
"The cabin was beautiful and very clean. The owner even left some muffins. The property is nicely maintained for a hike. Check in is easy and the owner is available if needed. I will stay there again next year. Highly recommend."
United States
Pam M.
$282 nightly
The price is $315
Dec 10 - Dec 11
Total with taxes and fees
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
Dining
The White Magnolia Cottage

The White Magnolia Cottage

Round Top
9.8 out of 10, Exceptional, (48)
"It was beautiful! And so clean! Perfect for a girl’s weekend!!"
United States
Tisha K.
$201 nightly
The price is $212
Dec 9 - Dec 10
Total with taxes and fees
The White Magnolia Cottage
Exterior detail
2/2 Secluded Home In Bastrop! 2mins from downtown 2mins From Bastrop Lake

2/2 Secluded Home In Bastrop! 2mins from downtown 2mins From Bastrop Lake

2.0 star property
Bastrop
10.0 out of 10, Exceptional, (2)
"Amazing host ! Did a great job making the stay feel like home . Beautiful place and very clean ! Host was outstanding great communication awesome amenities. 10/10 recommend will definitely continue booking here for future stays ! "
United States
Alex
$162 nightly
The price is $170
Dec 9 - Dec 10
Total with taxes and fees
2/2 Secluded Home In Bastrop! 2mins from downtown 2mins From Bastrop Lake
Private kitchen
Modern Retreat in the Pine Forest of Bastrop

Modern Retreat in the Pine Forest of Bastrop

2.0 star property
Bastrop
10.0 out of 10, Exceptional, (4)
"We had a great stay, house was immaculate, quiet neighborhood, loved it"
United States
Faye B.
$153 nightly
The price is $161
Dec 14 - Dec 15
Total with taxes and fees
Modern Retreat in the Pine Forest of Bastrop
Living area
Round Top Refuge Main House

Round Top Refuge Main House

2.0 star property
La Grange
10.0 out of 10, Exceptional, (3)
"Very Clean, Amazing Host, Wonderful location! Would definitely stay again!!"
United States
Colby W.
Round Top Refuge Main House
Exterior
Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting

La Grange
10.0 out of 10, Exceptional, (101)
"Such a beauty of a house! Highly recommend staying here if you are ever in Bastrop for the night! "
United States
Jim C.
$219 nightly
The price is $230
Dec 9 - Dec 10
Total with taxes and fees
Charming & Cozy Victorian in Quiet Residential Setting
Property grounds
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
10.0 out of 10, Exceptional, (17)
"We had a great time in this treehouse."
United States
Tandy S.
$190 nightly
The price is $212
Dec 9 - Dec 10
Total with taxes and fees
The Elf's Aerie, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire
Property grounds
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, (232)
"Great place, We had a good time"
United States
Corbet S.
$208 nightly
The price is $232
Dec 9 - Dec 10
Total with taxes and fees
The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire
Interior
Romance Glamping | Pup Paradise | Near River | ADA

Romance Glamping | Pup Paradise | Near River | ADA

Smithville
10.0 out of 10, Exceptional, (4)
"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.
$135 nightly
The price is $151
Dec 9 - Dec 10
Total with taxes and fees
Romance Glamping | Pup Paradise | Near River | ADA
Terrace/patio
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, (387)
"We enjoyed our stay."
Germany
Eva C.
$181 nightly
The price is $202
Dec 11 - Dec 12
Total with taxes and fees
The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire
1 bedroom, free WiFi, bed sheets
Charming Cottage, 5 Minutes to Round Top!

Charming Cottage, 5 Minutes to Round Top!

Round Top
9.0 out of 10, Wonderful, (2)
"Great stay. Second time to stay on this property and both houses were great."
United States
Anonymous traveler
Charming Cottage, 5 Minutes to Round Top!
Terrace/patio
The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire

The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire

Paige
10.0 out of 10, Exceptional, (215)
"Great stay at the Cactus House. Highly recommend if you need a little oasis in Paige Texas! "
United States
Georgia Y.
$206 nightly
The price is $230
Dec 9 - Dec 10
Total with taxes and fees
The Cactus House, A Serene Pet-Friendly Home in the 42 Acre 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

Best Western La Grange Inn & Suites

Best Western La Grange Inn & Suites

10/10 Excellent
"Friendly staff and great service "
daitwan 2-night trip
Posted 7 days 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 $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.

Explore a world of travel with Expedia

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?

Escape to Giddings - Charming 2-Bedroom Vacation Home: You might want to consider this vacation home rental near Winchester, which is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

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 Boat Lake. 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.