Holiday Rentals in Winchester

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Our top choices for Winchester holiday rentals

10.0 out of 10, Exceptional, (10 reviews)
"The little cabin was wonderful!! I loved sitting outside on the porch in the evening. It was very relaxing. "
United States
Lisa A.
The price is €130
includes taxes & fees
12 Jan - 13 Jan
Cozy Cottage With a View in 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
The price is €121
includes taxes & fees
12 Jan - 13 Jan
Adorable Guest Cabin In The Woods
10.0 out of 10, Exceptional, (1 review)
"The location right on the river was great!"
United States
Rachael H.
The price is €117
includes taxes & fees
14 Jan - 15 Jan
Terrys Water Front Bungalow on The RiversEdge AC Heat in a private campground!

Cabin in Schulenburg

Swiss Alp Texas Cabin
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.
The price is €146
includes taxes & fees
12 Jan - 13 Jan
Swiss Alp Texas Cabin
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.
The price is €152
includes taxes & fees
13 Jan - 14 Jan
Romance Glamping | Pup Paradise | Near River | ADA

Cabin in La Grange

Pinehaven Luxury Glamping
10.0 out of 10, Exceptional, (51 reviews)
"It was a very nice place to stay."
United States
Mike M.
The price is €154
includes taxes & fees
12 Jan - 13 Jan
Pinehaven Luxury Glamping
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
The price is €199
includes taxes & fees
17 Jan - 18 Jan
2/2 Secluded Home In Bastrop! 2mins from downtown 2mins From Bastrop Lake
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.
The price is €190
includes taxes & fees
12 Jan - 13 Jan
Elm Grove Camper- Less than 3 miles from Round Top proper

Cottage in Round Top

The White Magnolia Cottage
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.
The price is €190
includes taxes & fees
12 Jan - 13 Jan
The White Magnolia Cottage
10.0 out of 10, Exceptional, (1 review)
"This was amazing. Great stay. I love the Tiny Home. "
United States
Miguel Z.
The price is €158
includes taxes & fees
12 Jan - 13 Jan
Spacious 1-bedroom tinyhouse in the Bastrop pines near Bastrop’s SouthShore Lake
9.0 out of 10, Wonderful, (4 reviews)
"Amenities were plentiful."
United States
Karen G.
The price is €170
includes taxes & fees
9 Feb - 10 Feb
Charming Cottage, 5 Minutes to Round Top!
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.
The price is €277
includes taxes & fees
14 Jan - 15 Jan
Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await

Holiday Home in Fayette County

Enchanting Casita, 5 minutes to Round Top!
9.8 out of 10, Exceptional, (67 reviews)
"Awesome every-rime we stay. "
United States
Anonymous traveller
The price is €180
includes taxes & fees
9 Feb - 10 Feb
Enchanting Casita, 5 minutes to Round Top!
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
The price is €317
includes taxes & fees
12 Jan - 13 Jan
8 Minutes from Round Top! Your Silo-Bration Destination StoneHENge Silo #2
8.8 out of 10, Excellent, (10 reviews)
"Great property, will stay again. "
United States
Jerry A.
The price is €223
includes taxes & fees
12 Jan - 13 Jan
Lakefront Charm: Your Perfect Getaway in Round Top
The price is €70
includes taxes & fees
12 Jan - 13 Jan
Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse
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.
The price is €136
includes taxes & fees
12 Jan - 13 Jan
Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat
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
The price is €146
includes taxes & fees
12 Jan - 13 Jan
Riverside Romance/Luxury RV/Starry Skies & S'mores
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.
The price is €203
includes taxes & fees
12 Jan - 13 Jan
The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire
10.0 out of 10, Exceptional, (18 reviews)
"We had a great time in this treehouse."
United States
Tandy S.
The price is €184
includes taxes & fees
12 Jan - 13 Jan
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

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as €121 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday 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 holiday.

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 holiday rental in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winchester has to offer?

Modern Retreat in the Pine Forest of Bastrop: This holiday home rental outside of Winchester 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 wider area, you’ll find Bluff Creek Ranch and Buescher State Park.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.