Winchester Vacation Rentals

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Jan 10 - Jan 11
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Jan 11 - Jan 12
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Jan 16 - Jan 18
In two weeks
Jan 23 - Jan 25

Our top choices for Winchester vacation rentals

Property grounds
Cozy Cottage With a View in La Grange

Cozy Cottage With a View in La Grange

Cozy Cottage With a View in La Grange
La Grange
10.0 out of 10, Exceptional, (10 reviews)
"Lovely cottage on beautiful, peaceful property. It’s a very short drive to historic downtown La Grange. Be back in time for the fabulous sunset view from the porch!"
United States
Evelyn C.
$140 nightly
The price is $147
Jan 11 - Jan 12
Total with taxes and fees
Cozy Cottage With a View in La Grange
Exterior
Adorable Guest Cabin In The Woods

Adorable Guest Cabin In The Woods

Adorable Guest Cabin In The Woods
La Grange
9.8 out of 10, Exceptional, (66 reviews)
"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
Jan 11 - Jan 12
Total with taxes and fees
Adorable Guest Cabin In The Woods
1 bedroom, free WiFi
Terrys Water Front Bungalow on The RiversEdge AC Heat in a private campground!

Terrys Water Front Bungalow on The RiversEdge AC Heat in a private campground!

Terrys Water Front Bungalow on The RiversEdge AC Heat in a private campground!
2.0 star property
Smithville
10.0 out of 10, Exceptional, (1 review)
"The location right on the river was great!"
United States
Rachael H.
$120 nightly
The price is $126
Jan 11 - Jan 12
Total with taxes and fees
Terrys Water Front Bungalow on The RiversEdge AC Heat in a private campground!
1 bedroom, WiFi, bed sheets
Swiss Alp Texas Cabin

Swiss Alp Texas Cabin

Swiss Alp Texas Cabin
Schulenburg
9.8 out of 10, Exceptional, (8 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
Jan 11 - Jan 12
Total with taxes and fees
Swiss Alp Texas Cabin
Property grounds
Romance Glamping | Pup Paradise | Near River | ADA

Romance Glamping | Pup Paradise | Near River | ADA

Romance Glamping | Pup Paradise | Near River | ADA
Smithville
10.0 out of 10, Exceptional, (4 reviews)
"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.
$154 nightly
The price is $172
Jan 13 - Jan 14
Total with taxes and fees
Romance Glamping | Pup Paradise | Near River | ADA
Interior
Pinehaven Luxury Glamping

Pinehaven Luxury Glamping

Pinehaven Luxury Glamping
La Grange
10.0 out of 10, Exceptional, (51 reviews)
"It was a very nice place to stay."
United States
Mike M.
$166 nightly
The price is $175
Jan 11 - Jan 12
Total with taxes and fees
Pinehaven Luxury Glamping
Dining
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

2/2 Secluded Home In Bastrop! 2mins from downtown 2mins From Bastrop Lake
2.0 star property
Bastrop
10.0 out of 10, Exceptional, (3 reviews)
"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
$219 nightly
The price is $231
Jan 11 - Jan 12
Total with taxes and fees
2/2 Secluded Home In Bastrop! 2mins from downtown 2mins From Bastrop Lake
Interior
Elm Grove Camper- Less than 3 miles from Round Top proper

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 reviews)
"Great location so close to Round Top .The camper was perfect for two even three. Very clean and cozy . It was great to watch the cows chickens Roosters Goose while the sun was setting between the trees ."
United States
Mary Pat K.
$202 nightly
The price is $213
Jan 11 - Jan 12
Total with taxes and fees
Elm Grove Camper- Less than 3 miles from Round Top proper
Dining
The White Magnolia Cottage

The White Magnolia Cottage

The White Magnolia Cottage
Round Top
9.8 out of 10, Exceptional, (50 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.
$202 nightly
The price is $213
Jan 11 - Jan 12
Total with taxes and fees
The White Magnolia Cottage
Smart TV
Spacious 1-bedroom tinyhouse in the Bastrop pines near Bastrop’s SouthShore Lake

Spacious 1-bedroom tinyhouse in the Bastrop pines near Bastrop’s SouthShore Lake

Spacious 1-bedroom tinyhouse in the Bastrop pines near Bastrop’s SouthShore Lake
2.0 star property
Bastrop
10.0 out of 10, Exceptional, (1 review)
"This was amazing. Great stay. I love the Tiny Home. "
United States
Miguel Z.
$170 nightly
The price is $179
Jan 11 - Jan 12
Total with taxes and fees
Spacious 1-bedroom tinyhouse in the Bastrop pines near Bastrop’s SouthShore Lake
Dining
Charming Cottage, 5 Minutes to Round Top!

Charming Cottage, 5 Minutes to Round Top!

Charming Cottage, 5 Minutes to Round Top!
Round Top
9.0 out of 10, Wonderful, (4 reviews)
"Amenities were plentiful."
United States
Karen G.
$188 nightly
The price is $194
Jan 11 - Jan 12
Total with taxes and fees
Charming Cottage, 5 Minutes to Round Top!
Children's area
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await

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 reviews)
"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
Jan 13 - Jan 14
Total with taxes and fees
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await
1 bedroom, desk, WiFi, bed sheets
Enchanting Casita, 5 minutes to Round Top!

Enchanting Casita, 5 minutes to Round Top!

Enchanting Casita, 5 minutes to Round Top!
Fayette County
9.8 out of 10, Exceptional, (67 reviews)
"Awesome every-rime we stay. "
United States
Anonymous traveler
$200 nightly
The price is $206
Jan 11 - Jan 12
Total with taxes and fees
Enchanting Casita, 5 minutes to Round Top!
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

8 Minutes from Round Top! Your Silo-Bration Destination StoneHENge Silo #2
La Grange
9.8 out of 10, Exceptional, (42 reviews)
"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
Jan 11 - Jan 12
Total with taxes and fees
8 Minutes from Round Top! Your Silo-Bration Destination StoneHENge Silo #2
Exterior
Lakefront Charm: Your Perfect Getaway in Round Top

Lakefront Charm: Your Perfect Getaway in Round Top

Lakefront Charm: Your Perfect Getaway in Round Top
Fayette County
8.8 out of 10, Excellent, (10 reviews)
"Great property, will stay again. "
United States
Jerry A.
$245 nightly
The price is $251
Jan 11 - Jan 12
Total with taxes and fees
Lakefront Charm: Your Perfect Getaway in Round Top
Property grounds
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

Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse
1.0 star property
Smithville
$74 nightly
The price is $77
Jan 11 - Jan 12
Total with taxes and fees
Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse
Terrace/patio
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

Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
Smithville
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.
$147 nightly
The price is $154
Jan 11 - Jan 12
Total with taxes and fees
Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
Interior
Riverside Romance/Luxury RV/Starry Skies & S'mores

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

Riverside Romance/Luxury RV/Starry Skies & S'mores
Smithville
10.0 out of 10, Exceptional, (65 reviews)
"The area was near the river and i could see the stars at night. The sky both morning and night was beautiful. "
United States
veronica
$148 nightly
The price is $166
Jan 12 - Jan 13
Total with taxes and fees
Riverside Romance/Luxury RV/Starry Skies & S'mores
Property grounds
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

The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire
Paige
10.0 out of 10, Exceptional, (219 reviews)
"Only stayed one night as a stop over for a road trip to Port Aransas. Clean, quiet and secluded....just how I like it. Would stay again for longer."
United States
Kevin M.
$209 nightly
The price is $233
Jan 11 - Jan 12
Total with taxes and fees
The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire
Terrace/patio
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

The Elf's Aerie, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire
Paige
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
Jan 11 - Jan 12
Total with taxes and fees
The Elf's Aerie, An Enchanting Dog-Friendly Treehouse in the 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
"Second time staying here. Very friendly and helpful staff. Room was clean, bed was comfy."
Pamela 1-night trip
Posted 6 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?

Modern Retreat in the Pine Forest of Bastrop: You might want to consider this vacation home rental near Winchester, which has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 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.