Winchester Vacation Rentals

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Oct 3 - Oct 4
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Oct 4 - Oct 5
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Oct 3 - Oct 5
Next weekend
Oct 10 - Oct 12

Vacation Rentals in Winchester

Pinehaven Luxury Glamping
Terrace/patio

Pinehaven Luxury Glamping

10.0 out of 10, Exceptional, (47)
"Property was amazing. Private and quiet but within a few mins drive to Round Top. Wonderful experience. Will definitely book again. "
$184 nightly
The price is $194
Oct 5 - Oct 6
Total with taxes and fees
Pinehaven Luxury Glamping
Adorable Guest Cabin In The Woods
Private kitchen

Adorable Guest Cabin In The Woods

9.8 out of 10, Exceptional, (56)
"Great stay in a nice, relaxing cabin"
$129 nightly
The price is $136
Oct 5 - Oct 6
Total with taxes and fees
Adorable Guest Cabin In The Woods
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, (87)
"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."
$573 nightly
The price is $591
Oct 27 - Oct 28
Total with taxes and fees
Fun, eclectic Round Top home w/POOL! 5 min to town
Round Top Refuge Guest House
Outdoor dining

Round Top Refuge Guest House

10.0 out of 10, Exceptional, (4)
"Great place to stay! "
$205 nightly
The price is $216
Nov 3 - Nov 4
Total with taxes and fees
Round Top Refuge Guest House
The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire
Terrace/patio

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

10.0 out of 10, Exceptional, (213)
"Great place. Very comfortable. Only 10min to the lake. House had everything we needed. "
$210 nightly
The price is $235
Oct 6 - Oct 7
Total with taxes and fees
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
Property grounds

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

10.0 out of 10, Exceptional, (230)
"Clean, romantic, exactly what we were seeking!"
$211 nightly
The price is $235
Oct 5 - Oct 6
Total with taxes and fees
The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire
Waterfront Smithville River House
Exterior

Waterfront Smithville River House

9.8 out of 10, Exceptional, (60)
"We had a great time staying here as we explored the area. Property was as advertised, well kept, and very clean"
Waterfront Smithville River House
The White Magnolia Cottage
Dining

The White Magnolia Cottage

9.8 out of 10, Exceptional, (42)
"Perfect little cottage in fanstastic location in Warrenton. Clean, comfortable beds!"
$223 nightly
The price is $235
Oct 27 - Oct 28
Total with taxes and fees
The White Magnolia Cottage
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, (61)
"Amazing property. Very comfortable. Quiet and relaxing."
$203 nightly
The price is $209
Nov 2 - Nov 3
Total with taxes and fees
Enchanting Casita, 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!"
$190 nightly
The price is $196
Nov 2 - Nov 3
Total with taxes and fees
Historical country cabin in Round Top!
8 Minutes from Round Top! Your Silo-Bration Destination COOP-A-Cabana Silo #3
1 bedroom, free WiFi, bed sheets

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

9.8 out of 10, Exceptional, (59)
"Beautifully anointed silo! Wonderful accommodations for a country excursion!"
$339 nightly
The price is $357
Oct 20 - Oct 21
Total with taxes and fees
8 Minutes from Round Top! Your Silo-Bration Destination COOP-A-Cabana Silo #3
Charming Cottage, 5 Minutes to Round Top!
Interior

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!"
$190 nightly
The price is $196
Nov 2 - Nov 3
Total with taxes and fees
Charming Cottage, 5 Minutes to Round Top!
Sleep 40+ Lakeside Retreat on 53 Acre Ranch
Terrace/patio

Sleep 40+ Lakeside Retreat on 53 Acre Ranch

10.0 out of 10, Exceptional, (1)
"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!"
Sleep 40+ Lakeside Retreat on 53 Acre Ranch
The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire
Terrace/patio

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

10.0 out of 10, Exceptional, (385)
"As always, peaceful, clean and cute. Feels like home away from home! "
$190 nightly
The price is $212
Oct 6 - Oct 7
Total with taxes and fees
The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire
8 Minutes from Round Top! Your Silo-Bration Destination StoneHENge Silo #2
Exterior detail

8 Minutes from Round Top! Your Silo-Bration Destination StoneHENge Silo #2

9.8 out of 10, Exceptional, (39)
"Very easy check in and check out process."
$339 nightly
The price is $357
Oct 20 - Oct 21
Total with taxes and fees
8 Minutes from Round Top! Your Silo-Bration Destination StoneHENge Silo #2
Angeltom Cabin & RV:20 Acre Woods - >16 pip + Jacuzzi + treehouse + UTV + 2ponds
Smart TV, fireplace, video games, DVD player

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

10.0 out of 10, Exceptional, (105)
"Always have an awesome experience here! "
Angeltom Cabin & RV:20 Acre Woods - >16 pip + Jacuzzi + treehouse + UTV + 2ponds
Charming & Cozy Victorian in Quiet Residential Setting
Exterior

Charming & Cozy Victorian in Quiet Residential Setting

10.0 out of 10, Exceptional, (95)
"My mom and I enjoyed our stay; the house was clean, well stocked and in a good neighborhood. The owner was quick to respond to messages and had an easy check in and out process. "
$236 nightly
The price is $249
Oct 26 - Oct 27
Total with taxes and fees
Charming & Cozy Victorian in Quiet Residential Setting
TuscanyNTexas
Outdoor pool, a heated pool

TuscanyNTexas

10.0 out of 10, Exceptional, (24)
"Beautiful accommodations!"
$1,028 nightly
The price is $1,082
Oct 7 - Oct 8
Total with taxes and fees
TuscanyNTexas
Retreat Center, sleeps 60, with 20 people minimum - 50 a day, per person
Property grounds

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

1.0 star property
$170 nightly
The price is $179
Oct 5 - Oct 6
Total with taxes and fees
Retreat Center, sleeps 60, with 20 people minimum - 50 a day, per person
Walkable Cottage w/Fire Pit | 15 min from Round Top | Francis @ Grace Inn
Smart TV

Walkable Cottage w/Fire Pit | 15 min from Round Top | Francis @ Grace Inn

$635 nightly
The price is $692
Oct 6 - Oct 7
Total with taxes and fees
Walkable Cottage w/Fire Pit | 15 min from Round Top | Francis @ Grace Inn
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

Giddings Executive Inn

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. "
Patricia 2-night trip
Posted 4 days ago
Giddings Executive Inn

Find out more about Winchester

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

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?

Fun, eclectic Round Top home w/POOL! 5 min to town: Visitors like this Winchester vacation home rental. It is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, an oven, and a microwave, so you can cook with friends or family.

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 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.