Winchester Holiday Rentals

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Holiday Rentals in Winchester

Our top choices for Winchester holiday rentals

Pinehaven Luxury Glamping

10.0 out of 10, Exceptional, (45)
"My girlfriend and I really enjoyed the property and the location. Everything about the stay was phenomenal and accommodating! Highly recommend!"
The price is NZ$371
includes taxes & fees
24 Sept - 25 Sept
Pinehaven Luxury Glamping

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."
The price is NZ$1,007
includes taxes & fees
24 Sept - 25 Sept
Fun, eclectic Round Top home w/POOL! 5 min to town

Round Top Refuge Guest House

10.0 out of 10, Exceptional, (4)
"Great place to stay! "
The price is NZ$327
includes taxes & fees
24 Sept - 25 Sept
Round Top Refuge Guest House

Adorable Guest Cabin In The Woods

9.8 out of 10, Exceptional, (56)
"Great stay in a nice, relaxing cabin"
The price is NZ$231
includes taxes & fees
29 Sept - 30 Sept
Adorable Guest Cabin In The Woods

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

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

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!"
The price is NZ$329
includes taxes & fees
24 Sept - 25 Sept
Charming Cottage, 5 Minutes to Round Top!

The White Magnolia Cottage

9.8 out of 10, Exceptional, (42)
"Perfect little cottage in fanstastic location in Warrenton. Clean, comfortable beds!"
The price is NZ$359
includes taxes & fees
24 Sept - 25 Sept
The White Magnolia Cottage

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. "
The price is NZ$391
includes taxes & fees
24 Sept - 25 Sept
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

10.0 out of 10, Exceptional, (230)
"Clean, romantic, exactly what we were seeking!"
The price is NZ$389
includes taxes & fees
24 Sept - 25 Sept
The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire

Charming & Cozy Victorian in Quiet Residential Setting

10.0 out of 10, Exceptional, (94)
"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. "
The price is NZ$389
includes taxes & fees
29 Sept - 30 Sept
Charming & Cozy Victorian in Quiet Residential Setting

Rustic Charm in our Quaint Round Top Farmhouse!

10.0 out of 10, Exceptional, (2)
"We loved out stay in the cooper house!"
The price is NZ$537
includes taxes & fees
24 Sept - 25 Sept
Rustic Charm in our Quaint Round Top Farmhouse!

Cozy cabin in the pines of Bastrop with AC, WiFi

10.0 out of 10, Exceptional, (2)
"The cabin was so nice and the back deck was so calming and restful.."
Cozy cabin in the pines of Bastrop with AC, WiFi

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

10.0 out of 10, Exceptional, (104)
"Always have an awesome experience here! "
Angeltom Cabin & RV:20 Acre Woods - >16 pip + Jacuzzi + treehouse + UTV + 2ponds

Historical country cabin in Round Top!

10.0 out of 10, Exceptional, (2)
"great location, would come back again!"
The price is NZ$329
includes taxes & fees
24 Sept - 25 Sept
Historical country cabin in Round Top!

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

1.0 star property
The price is NZ$305
includes taxes & fees
23 Oct - 24 Oct
Retreat Center, sleeps 60, with 20 people minimum - 50 a day, per person

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

9.8 out of 10, Exceptional, (21)
"Very nice place that is well maintained. Will certainly stay again when visiting the area."
The price is NZ$5,130
includes taxes & fees
18 Oct - 19 Oct
Round Top Gem | Casa Tres Hermanas | Pool + Hot Tub + Fire Pit + Grill

Escape to Giddings - Charming 2-Bedroom Vacation Home

10.0 out of 10, Exceptional, (139)
"Relaxing and beautiful property "
Escape to Giddings - Charming 2-Bedroom Vacation Home

The Country Cottage w/ Beautiful Views-5 mi. from historic downtown

9.8 out of 10, Exceptional, (93)
"Adventured from Florida to check-out Round Top TX and the antique extravaganza … this quaint country cottage , was centrally located to all the surrounding cities. It was very quiet and offered what we needed for the stay. "
The Country Cottage w/ Beautiful Views-5 mi. from historic downtown

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

The price is NZ$1,388
includes taxes & fees
3 Oct - 4 Oct
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

Find out more about Winchester

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, 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 NZ$231 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?

Escape to Giddings - Charming 2-Bedroom Vacation Home: This holiday home rental outside of Winchester is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games 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 Zula B Wylie Library and Bluff Creek Ranch.

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.