Winchester Holiday Rentals

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Holiday Rentals in Winchester

Pool & Hot Tub in Sunny Smithville Getaway!

10.0 out of 10, Exceptional, (15)
"House was perfect pool was great Great communication with host We will be back"
Pool & Hot Tub in Sunny Smithville Getaway!

Pinehaven Luxury Glamping

10.0 out of 10, Exceptional, (41)
"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$356
includes taxes & fees
8 July - 9 July
Pinehaven Luxury Glamping

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

10.0 out of 10, Exceptional, (378)
"Very close to activities we had planned. "
The price is NZ$354
includes taxes & fees
22 July - 23 July
The Cottage, A Tranquil Pet-Friendly Retreat on 42 Acres at Lost Pines Shire

Waterfront Smithville River House

9.8 out of 10, Exceptional, (60)
"Cabin was very cute and cozy. Nice and quiet. The hot water wasn’t working for us. Other than that it was lovely. "
Waterfront Smithville River House

Adorable Guest Cabin In The Woods

9.8 out of 10, Exceptional, (51)
"Great stay in a nice, relaxing cabin"
The price is NZ$224
includes taxes & fees
8 July - 9 July
Adorable Guest Cabin In The Woods

Charming & Cozy Victorian in Quiet Residential Setting

10.0 out of 10, Exceptional, (91)
"Good location. Quiet neighborhood."
The price is NZ$378
includes taxes & fees
14 July - 15 July
Charming & Cozy Victorian in Quiet Residential Setting

Charming Victorian Bike to Shops, Mins to Antiques & Wedding Venues

10.0 out of 10, Exceptional, (50)
"Beautiful historic property in a quint little town… and close to Round Top and antiquing! Our host was great to work with and very accommodating. We’ll stay again for sure. "
Charming Victorian Bike to Shops, Mins to Antiques & Wedding Venues

Sleep 40+ Lakeside Retreat on 53 Acre Ranch

Sleep 40+ Lakeside Retreat on 53 Acre Ranch

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

10.0 out of 10, Exceptional, (226)
"So cute definitely coming back "
The price is NZ$403
includes taxes & fees
4 Aug - 5 Aug
The Hobbit's Nest, A Magical Dog-friendly Treehouse in the Lost Pines Shire

Lost Pine Retreat: Charming 4-bedroom House

10.0 out of 10, Exceptional, (1)
"Great place. Spacious and comfortable."
Lost Pine Retreat: Charming 4-bedroom House

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!"
The price is NZ$1,375
includes taxes & fees
8 July - 9 July
Round Top entertainer's oasis w/POOL, Pond & more!

Cottage with pool in historic downtown

10.0 out of 10, Exceptional, (205)
"Cute cottage. Great location, quiet neighborhood, clean, and historic downtown. "
Cottage with pool in historic downtown

Beautiful, Modern Apartment in La Grange- Great Location!

9.6 out of 10, Exceptional, (9)
"Great communication with owner."
The price is NZ$375
includes taxes & fees
17 July - 18 July
Beautiful, Modern Apartment in La Grange- Great Location!

The White Magnolia Cottage

9.8 out of 10, Exceptional, (38)
"A wonderful place to stay with a perfect location"
The price is NZ$353
includes taxes & fees
8 July - 9 July
The White Magnolia Cottage

Round Top charm w/POOL and outdoor dining

9.8 out of 10, Exceptional, (78)
"The location is great. Super cute house with everything you need"
Round Top charm w/POOL and outdoor dining

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

10.0 out of 10, Exceptional, (210)
"Tucked away is this little gem of a house. Amazing stay. Spacious and well maintained. "
The price is NZ$387
includes taxes & fees
5 Aug - 6 Aug
The Cactus House, A Serene Pet-Friendly Home in the 42 Acre Lost Pines Shire

Whispering Winds~ Kayaking, Tubing, Fishing and Fun!

9.8 out of 10, Exceptional, (78)
"We so enjoyed a relaxing weekends at WW. Great location, awesome amenities. Lots of room! "
The price is NZ$1,043
includes taxes & fees
10 July - 11 July
Whispering Winds~ Kayaking, Tubing, Fishing and Fun!

Relaxing 2-bedroom cabin on Lake Jean

9.6 out of 10, Exceptional, (5)
"Great stay at the cabin! Owners were super communicative and thought of everything! Great location and wonderful beds. We used the boat, the paddle boat, the grill for burgers and the fire pit. It was a wonderful trip! Would love to go again. "
Relaxing 2-bedroom cabin on Lake Jean

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

10.0 out of 10, Exceptional, (103)
"Always have an awesome experience here! "
Angeltom Cabin & RV:20 Acre Woods - >16 pip + Jacuzzi + treehouse + UTV + 2ponds

Gaviota Home in The Lost Pines

8.6 out of 10, Excellent, (11)
"Place is great to get out of the city and soak up some pine trees air 🌲"
Gaviota Home in The Lost Pines
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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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?

Waterfront Smithville River House: This holiday home rental outside of Winchester is located on the waterfront, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.