Winchester Holiday Rentals from €113: Search Short-Term Rentals

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

Round Top Refuge Guest House : This holiday home rental outside of Winchester offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Make the most of garden in this rental home to help you unwind.

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Holiday Rentals in Winchester

"Property was amazing. Private and quiet but within a few mins drive to Round Top. Wonderful experience. Will definitely book again. "

includes taxes & fees

19 Oct - 20 Oct

"Great stay in a nice, relaxing cabin"

includes taxes & fees

19 Oct - 20 Oct

"We had a wonderful stay at this charming, rustic antique home! The location was perfect—just minutes from town but tucked away in a peaceful country setting. The pool was absolutely lovely and made for relaxing afternoons. The whole place was quiet, cozy, and felt like a true home away from home. The beds were super comfortable too! Highly recommend for anyone looking for a restful and scenic getaway."

includes taxes & fees

27 Oct - 28 Oct

"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!"

includes taxes & fees

12 Oct - 13 Oct

"Great place to stay! "

includes taxes & fees

3 Nov - 4 Nov

"Enjoyed our stay!!! Just being away from the city and enjoying the quiet countryside was great! The property was excellent for our family of six! Host was available to reach and answered all our questions."

"The Cactus House was comfortable! Sitting on the swing on the back porch was relaxing! We had a very nice stay!"

includes taxes & fees

22 Oct - 23 Oct

"Excellent place to relax and have a good time."

includes taxes & fees

28 Oct - 29 Oct

Coffee/tea maker, cookware/dishes/utensils

"Amazing property. Very comfortable. Quiet and relaxing."

includes taxes & fees

2 Nov - 3 Nov

"great location, would come back again!"

includes taxes & fees

2 Nov - 3 Nov

"Very nice place that is well maintained. Will certainly stay again when visiting the area."

"Beautifully anointed silo! Wonderful accommodations for a country excursion!"

includes taxes & fees

20 Oct - 21 Oct

"My daughter and I had a great time in Round Top . We did lots of shopping and eating in fine restaurants. The charming cottage we stayed at was clean and cozy. It was small , but efficient for our needs. Location was perfect. Cant wsit to come back in October when its cooler!"

"This is an amazing place to stay if you are a small church like us and want a great place to have a retreat. I highly recommend this place if you want to get out of the city and connect with Jesus!"

"This was a great place and perfect for seeing Smithville and all of it's wonderful places and people."

Smart TV, fireplace, video games, DVD player

"1st time renting this place. But it certainly won't be the last. Had a little family vacation for the 4th of July and this place was so nice, clean and it literally has EVERYTHING! The kids had so much fun exploring, fishing and just spending time outside. The owners are so nice and sweet. They answered quickly to any questions i had. For sure a place to stay at for families. "

"We enjoyed our stay."

includes taxes & fees

13 Oct - 14 Oct

"Had the best time deer are.present and the cabin is gorgeous! Host was amazing"

includes taxes & fees

22 Oct - 23 Oct

includes taxes & fees

12 Oct - 13 Oct

"Beautiful, quiet, historic yet modern!!"

includes taxes & fees

19 Oct - 20 Oct

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Top Winchester Hotel Reviews

Adorable Guest Cabin In The Woods

10/10 Excellent

"Great location! The hosts are very helpful and easy to be in contact with. Check in was extremely easy and their directions are accurate and easy to follow to find their property and where to park, etc. on property.Beds are comfortable, WiFi is available and fast, quiet and safe location, property is beautiful, loved having the deer feeder in view of the cabin- got to see some deer eating in the morning and at night. It was 7 minutes from the wedding we attended and tucked far enough back from 153 there was not road noise for us- despite it being not very far down 153.We would come back and stay again if it’s available when we come and see family again.Thank you for the great stay!"

Cozy Cottage With a View in La Grange

10/10 Excellent

"The entire experience was seamless from start to finish. Communication from the owners was prompt and clear throughout our stay. The cottage was exceptionally clean, tastefully updated, and very comfortable. The AC and fans kept the cottage very cool and comfortable the entire time in this Texas heat. The shower was also a particularly enjoyable feature. The view of the lake was serene, quiet and peaceful. Ive stayed at many cottage rentals and this one was absolutely top notch and we would certainly stay again. "

Giddings Executive Inn

10/10 Excellent

"The Giddings Executive Inn is an old Inn but owners have clean room, but no amenities such as paper tissues; no breakfast served; no white fluffy towels. Outside is very dated and not the best condition. Jay, the owner, is very friendly, helpful and cordial. The Inn was very busy with out-of-town workers but they were exceptionally quiet. "

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 €113 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?

Round Top Refuge Guest House: This holiday home rental outside of Winchester offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Make the most of garden 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 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.

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Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Pinehaven Luxury Glamping

Adorable Guest Cabin In The Woods

Fun, eclectic Round Top home w/POOL! 5 min to town

Cozy Cottage With a View in La Grange

Round Top Refuge Guest House

Waterfront Smithville River House

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

The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire

Enchanting Casita, 5 minutes to Round Top!

Historical country cabin in Round Top!

Round Top Gem | Casa Tres Hermanas | Pool + Hot Tub + Fire Pit + Grill

8 Minutes from Round Top! Your Silo-Bration Destination COOP-A-Cabana Silo #3

Charming Cottage, 5 Minutes to Round Top!

Sleep 40+ Lakeside Retreat on 53 Acre Ranch

Short cottage

Angeltom Cabin & RV:20 Acre Woods - >16 pip + Jacuzzi + treehouse + UTV + 2ponds

The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire

PineyWoods House Forest Retreat

Retreat Center, sleeps 60, with 20 people minimum - 50 a day, per person

Charming & Cozy Victorian in Quiet Residential Setting

Top Winchester Hotel Reviews

Adorable Guest Cabin In The Woods

Cozy Cottage With a View in La Grange

Studio 6 – Giddings, Tx

Pinehaven Luxury Glamping

The Oak Motel

Giddings Executive Inn

Budget Inn Giddings by Mukhi Hotels

Hampton Inn La Grange

Country Inn-Giddings

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Frequently asked questions

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