Best Resorts in Winchester

    price find illustration
    Change your mind
    Our total price for your stay includes taxes and fees
    deals illustration
    Treat yourself
    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Resorts in Winchester

We don't have any properties that match your exact search

Recommended hotels in Winchester

RanchHouze in Round Top
Books, music library, stereo

RanchHouze in Round Top

10.0 out of 10, Exceptional, (1)
$621 nightly
The price is $653
Jun 29 - Jun 30
Total includes taxes and fees
RanchHouze in Round Top
RanchHouze East in Round Top
Books, music library, stereo

RanchHouze East in Round Top

10.0 out of 10, Exceptional, (1)
"Property was very easy to access, close to shopping. House was very clean, plenty of towels. Missed having at least one TV during our stay, more so because of basketball playoffs in the evening. Living room furniture didn't scream "come sit on me"; but, was ok. Overall, property makes for a good stay; I'd stay again."
$872 nightly
The price is $917
Jun 29 - Jun 30
Total includes taxes and fees
RanchHouze East in Round Top
Hotel Bebe | Bungalow 3 | Pool+Fire Pit
Pool

Hotel Bebe | Bungalow 3 | Pool+Fire Pit

5.6 out of 10, (4)
"Very quaint little cabin. A good glamping location with the bonus of a pool. Restaurants and shopping close by, but be prepared if during antique market as the road is packed!"
$276 nightly
The price is $285
Jun 26 - Jun 27
Total includes taxes and fees
Hotel Bebe | Bungalow 3 | Pool+Fire Pit
Hotel Bebe | Bungalow 2 | Pool+Fire Pit
Pool

Hotel Bebe | Bungalow 2 | Pool+Fire Pit

8.4 out of 10, Very Good, (9)
"Wow, what a great stay in Round Top! Perfect location and so pretty!"
$306 nightly
The price is $316
Jun 26 - Jun 27
Total includes taxes and fees
Hotel Bebe | Bungalow 2 | Pool+Fire Pit
Hotel Bebe | Pool Bungalow | Pool+Fire Pit
Pool

Hotel Bebe | Pool Bungalow | Pool+Fire Pit

9.2 out of 10, Wonderful, (7)
"great location for round top show!! "
$320 nightly
The price is $332
Jun 26 - Jun 27
Total includes taxes and fees
Hotel Bebe | Pool Bungalow | Pool+Fire Pit
Hotel Bebe | Bungalow 1 | Pool+Fire Pit
Exterior

Hotel Bebe | Bungalow 1 | Pool+Fire Pit

7.6 out of 10, Good, (5)
"Great place"
$367 nightly
The price is $381
Jun 26 - Jun 27
Total includes taxes and fees
Hotel Bebe | Bungalow 1 | Pool+Fire Pit
A Sanctuary of Stories!
Outdoor dining

A Sanctuary of Stories!

8.6 out of 10, Excellent, (4)
"We loved the house but were surprised when other visitors drove in to stay at guest house. We didn’t see anything about the guest house on the property when we booked. Just would have liked to know that there was another party staying there. "
$538 nightly
The price is $567
Jun 26 - Jun 27
Total includes taxes and fees
A Sanctuary of Stories!
Lakefront Charm: Your Perfect Getaway in Round Top
Terrace/patio

Lakefront Charm: Your Perfect Getaway in Round Top

9.2 out of 10, Wonderful, (5)
"Beautiful place. As advertised. Would stay again. Loved it! Just remember, Round Top shops/restaurants are generally only open Thurs-Sunday. We drove to cute surrounding towns like Brenham, Fayetteville and La Grange for meals out and drinks. "
$247 nightly
The price is $253
Jun 26 - Jun 27
Total includes taxes and fees
Lakefront Charm: Your Perfect Getaway in Round Top
Round Top entertainer's oasis w/POOL, Pond & more!
Pool

Round Top entertainer's oasis w/POOL, Pond & more!

9.4 out of 10, Exceptional, (3)
"This place was amazing! The two of us needed a weekend away and happy to have found this one. I was inspired to redecorate my house when we got back :) If you’re going when it’s cold-just make sure that the heat issue in the master room is resolved or that they have a heater in there, as we had some issues with that but the rest of the house was super cozy and warm. Would definitely recommend!"
$815 nightly
The price is $840
Jun 26 - Jun 27
Total includes taxes and fees
Round Top entertainer's oasis w/POOL, Pond & more!
Enchanting Casita, 5 minutes to Round Top!
Coffee/tea maker, cookware/dishes/utensils

Enchanting Casita, 5 minutes to Round Top!

9.8 out of 10, Exceptional, (60)
"Had a great stay here! Clean space and easy communication with host. Would definitely stay here again."
$201 nightly
The price is $207
Jun 29 - Jun 30
Total includes taxes and fees
Enchanting Casita, 5 minutes to Round Top!
Charming Cottage, 5 Minutes to Round Top!
1 bedroom, free WiFi, bed sheets

Charming Cottage, 5 Minutes to Round Top!

9.0 out of 10, Wonderful, (2)
"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!"
$202 nightly
The price is $208
Jun 26 - Jun 27
Total includes taxes and fees
Charming Cottage, 5 Minutes to Round Top!
Historical country cabin in Round Top!
Outdoor dining

Historical country cabin in Round Top!

10.0 out of 10, Exceptional, (2)
"great location, would come back again!"
$194 nightly
The price is $201
Jun 29 - Jun 30
Total includes taxes and fees
Historical country cabin in Round Top!
Rustic Charm in our Quaint Round Top Farmhouse!
Interior

Rustic Charm in our Quaint Round Top Farmhouse!

10.0 out of 10, Exceptional, (2)
"We loved out stay in the cooper house!"
$326 nightly
The price is $335
Jun 26 - Jun 27
Total includes taxes and fees
Rustic Charm in our Quaint Round Top Farmhouse!
Designory Round Top home, scenic views & pond!
Fridge, microwave, oven, dishwasher

Designory Round Top home, scenic views & pond!

10.0 out of 10, Exceptional, (5)
"So charming! Beautifully appointed. Design and the feel were perfect for our weekend. The pond setting and property were quiet and peaceful. It was the icing on the cake for our first amazing RT experience."
$576 nightly
The price is $594
Jun 26 - Jun 27
Total includes taxes and fees
Designory Round Top home, scenic views & pond!
Fun, eclectic Round Top home w/POOL! 5 min to town
Pool

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

9.8 out of 10, Exceptional, (85)
"We really enjoyed having the house to ourselves! The location was perfect, the bedding was great, the inside of the house was clean, decorated with a cute Warrenton antique flair and lots of outdoor seating."
$576 nightly
The price is $594
Jun 26 - Jun 27
Total includes taxes and fees
Fun, eclectic Round Top home w/POOL! 5 min to town
Farmstead Round Top
Garden

Farmstead Round Top

3.0 star property
9.8 out of 10, Exceptional, (46)
"Love our stay in Round Top. The facilities are great, clean, modern and quiet"
$227 nightly
The price is $238
Jul 21 - Jul 22
Total includes taxes and fees
Farmstead Round Top
The Remarkable Room Six
1 bedroom

The Remarkable Room Six

10.0 out of 10, Exceptional, (1)
"We have been staying here for years and the property is constantly improving!! Definitely a must for roundtop!"
$232 nightly
The price is $244
Jul 16 - Jul 17
Total includes taxes and fees
The Remarkable Room Six
The Elegant Room Three
1 bedroom

The Elegant Room Three

$265 nightly
The price is $279
Jul 24 - Jul 25
Total includes taxes and fees
The Elegant Room Three
The Addi - Farmstead
1 bedroom, WiFi, bed sheets

The Addi - Farmstead

10.0 out of 10, Exceptional, (1)
"VRBO accidentally has this listed as a 2 bedroom rental. It is actually a 1 bedroom. The property manager was wonderful to work with and we worked out a solution. The rental was very clean and organized, modern finishes, amazing shower, towels and robes. We absolutely loved our stay here. "
$354 nightly
The price is $372
Jul 18 - Jul 19
Total includes taxes and fees
The Addi - Farmstead
The Graceful Room Five
Terrace/patio

The Graceful Room Five

$265 nightly
The price is $279
Jul 24 - Jul 25
Total includes taxes and fees
The Graceful Room Five
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

What is Winchester like for a resort vacation?
You deserve a getaway, and a resort is the perfect place to find all the services and amenities you need for a relaxing trip to Winchester. One of the comfortable resorts in the area might be just what you're searching for, whether you're hoping for a luxurious suite, shopping possibilities, or fun activities to try.
What's a top resort for my stay in Winchester?
Here's our top-rated resort near Winchester: Luxury Ranch Retreat with Pool, Hike & Bike Trails & Golf-Close to COTA & Austin - Family-friendly resort. 17.4 mi (27.9 km) from Winchester. Features a car charging station, a garden, and a hot tub.
What can I do in Winchester?
If you're interested in local sights, Bluff Creek Ranch, The Bugle Boy, and Buescher State Park are some places to visit nearby. Other attractions in the area include Lee County Courthouse and Cotton Bowl Speedway.
What's the weather like in Winchester?
The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 55°F. Average annual precipitation for Winchester is 41 inches.
What's the best way to get to and around Winchester?
Fly into Austin-Bergstrom Intl. Airport (AUS), which is located 41.3 mi (66.4 km) away from the heart of the city. If you'd like to explore around the area, you may want to rent a car for your trip.