Winchester Vacation Rentals

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In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Winchester vacation rentals

Exterior

Cabin in La Grange

Adorable Guest Cabin In The Woods
9.8 out of 10, Exceptional, (71 reviews)
"Quiet and close to nature. "
United States
Andy
$139 nightly
The price is $146
Mar 30 - Mar 31
Total with taxes and fees
Adorable Guest Cabin In The Woods
Property grounds

Cottage in La Grange

Cozy Cottage With a View in La Grange
10.0 out of 10, Exceptional, (10 reviews)
"Very nice retreat to stay in the La Grange area. The property couldn’t be more beautiful. The coffee they stock is amazing as well. "
United States
Andrew W.
$154 nightly
The price is $162
Mar 6 - Mar 7
Total with taxes and fees
Cozy Cottage With a View in La Grange
1 bedroom, WiFi, bed sheets

Cabin in Schulenburg

Swiss Alp Texas Cabin
9.8 out of 10, Exceptional, (9 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
Mar 6 - Mar 7
Total with taxes and fees
Swiss Alp Texas Cabin
Interior

Cabin in La Grange

Pinehaven Luxury Glamping
10.0 out of 10, Exceptional, (55 reviews)
"It was a very nice place to stay."
United States
Mike M.
$199 nightly
The price is $210
Apr 5 - Apr 6
Total with taxes and fees
Pinehaven Luxury Glamping
Exterior

Vacation Home in Fayette County

Lakefront Charm: Your Perfect Getaway in Round Top
8.2 out of 10, Very Good, (11 reviews)
"We had a great stay. The home was clean. The area was restful. Everything was as described. We highly recommend it!"
United States
Joshua C.
$489 nightly
The price is $507
Mar 7 - Mar 8
Total with taxes and fees
Lakefront Charm: Your Perfect Getaway in Round Top
Children's area

Cabin in Paige

Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
9.8 out of 10, Exceptional, (19 reviews)
"The property at Blessing Ranch in Paige, Tx was Very relaxing and peaceful. Not too far from dining and shopping, yet off the main road for privacy. The house is immaculate with all modern finishes and appliances. Very comfortable beds. Exceeded my expectations."
United States
Richard
$282 nightly
The price is $315
Mar 9 - Mar 10
Total with taxes and fees
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
Terrace/patio

Vacation Home in Paige

The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire
10.0 out of 10, Exceptional, (391 reviews)
"This was our third visit here and we just loved it!!! Such a relaxing getaway, we will be back for sure!"
United States
Lyn M.
$190 nightly
The price is $212
Mar 10 - Mar 11
Total with taxes and fees
The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire
Interior

Mobile Home in Round Top

Elm Grove Camper- Less than 3 miles from Round Top proper
9.6 out of 10, Exceptional, (27 reviews)
"This is our 3rd time staying with this host for the fall antique show and have had a pleasant stay each time. "
United States
Shawna M.
$205 nightly
The price is $216
Mar 6 - Mar 7
Total with taxes and fees
Elm Grove Camper- Less than 3 miles from Round Top proper
Exterior

Vacation Home in La Grange

Round Top Refuge Guest House
10.0 out of 10, Exceptional, (7 reviews)
"Wonderful light and bright place to stay near RoundTop!!"
United States
Jennifer S.
$335 nightly
The price is $352
Mar 6 - Mar 7
Total with taxes and fees
Round Top Refuge Guest House
Exterior

Vacation Home in Fayette County

Enchanting Casita, 5 minutes to Round Top!
9.8 out of 10, Exceptional, (68 reviews)
"My daughter and I loved staying at Enchanting Casita! Such a cute little cottage and great location! Perfect place to relax after a long day of shopping in Round Top."
United States
Michelle L.
$674 nightly
The price is $704
Mar 6 - Mar 7
Total with taxes and fees
Enchanting Casita, 5 minutes to Round Top!
Property grounds

Cabin in Paige

The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire
10.0 out of 10, Exceptional, (232 reviews)
"Fantastic stay! The treehouse is quite charming with thoughtful Tolkien touches. The property is secluded and makes you feel as though you have the place all to yourself. Would definitely stay again!"
United States
Allen L.
$204 nightly
The price is $228
Mar 8 - Mar 9
Total with taxes and fees
The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire
Terrace/patio

Cabin in Paige

The Elf's Aerie, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire
10.0 out of 10, Exceptional, (18 reviews)
"We had a great time in this treehouse."
United States
Tandy S.
$189 nightly
The price is $211
Mar 10 - Mar 11
Total with taxes and fees
The Elf's Aerie, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire
Property grounds

Cabin in Smithville

Dodo's Place on 22 acres outside of Smithville, TX
10.0 out of 10, Exceptional, (1 review)
"The host was great it cozy and peaceful would definitely stay here again when I am in the area"
United States
Cutter H.
$158 nightly
The price is $166
Mar 6 - Mar 7
Total with taxes and fees
Dodo's Place on 22 acres outside of Smithville, TX
Smart TV, DVD player, books, stereo

Vacation Home in Smithville

Lost Pines Lake House near Bastrop State Park and Buescher State Park..
9.0 out of 10, Wonderful, (34 reviews)
"We had very good and clean and comfortable accommodations. "
United States
Peter W.
$187 nightly
The price is $197
Mar 12 - Mar 13
Total with taxes and fees
Lost Pines Lake House near Bastrop State Park and Buescher State Park..
Terrace/patio

Apartment in Smithville

Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
9.0 out of 10, Wonderful, (2 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.
$142 nightly
The price is $149
Mar 30 - Mar 31
Total with taxes and fees
Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
Outdoor dining

Cabin in Bastrop

Premium Lakefront Cabin #1: The Armadillo (Austin)
$316 nightly
The price is $339
Mar 10 - Mar 11
Total with taxes and fees
Premium Lakefront Cabin #1: The Armadillo (Austin)
Property grounds

Vacation Home in Paige

The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire
10.0 out of 10, Exceptional, (223 reviews)
"Great stay at the Cactus House. Highly recommend if you need a little oasis in Paige Texas! "
United States
Georgia Y.
$209 nightly
The price is $233
Mar 8 - Mar 9
Total with taxes and fees
The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire
Dining

Cottage in Round Top

The White Magnolia Cottage
9.8 out of 10, Exceptional, (54 reviews)
"Great location for the Round Top Antiques Fair. Stayed only for a night but enjoyed our stay, hopefully will be back again! "
United States
Hannah M.
$221 nightly
The price is $233
Mar 30 - Mar 31
Total with taxes and fees
The White Magnolia Cottage
Exterior

Vacation Home in La Grange

Charming & Cozy Victorian in Quiet Residential Setting
10.0 out of 10, Exceptional, (107 reviews)
"Such a beauty of a house! Highly recommend staying here if you are ever in Bastrop for the night! "
United States
Jim C.
$239 nightly
The price is $252
Apr 1 - Apr 2
Total with taxes and fees
Charming & Cozy Victorian in Quiet Residential Setting
Living area

Vacation Home in La Grange

Round Top Refuge Main House
10.0 out of 10, Exceptional, (3 reviews)
"Very Clean, Amazing Host, Wonderful location! Would definitely stay again!!"
United States
Colby W.
$299 nightly
The price is $315
Mar 8 - Mar 9
Total with taxes and fees
Round Top Refuge Main 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
"Yes the room was great, the only thing I would have done different on my end was to request a room on the lower floors due to having a little trouble walking some. T he little coffee maker did not have anything to mix your coffee with, but overall a great rest and visit."
robert 1-night trip
Posted 4 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 $197 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?

Short cottage: You might want to consider this vacation rental near Winchester, which offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books 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 Tejas Lake. In the larger area, you’ll find Bluff Creek Ranch and Cotton Bowl Speedway.

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.