Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 21 - Nov 23
In two months
Jan 2 - Jan 4
In three months
Jan 30 - Feb 1
In four months
Feb 27 - Mar 1

Vacation Rentals in Winchester

Dining
The White Magnolia Cottage

The White Magnolia Cottage

Round Top
9.8 out of 10, Exceptional, (44)
"Very clean and perfect for the 4 of us for a night at round top! "
United States
Catherine C.
The price is ￥27,616
￥33,108 total
includes taxes & fees
Nov 10 - Nov 11
The White Magnolia Cottage
Exterior
Charming & Cozy Victorian in Quiet Residential Setting

Charming & Cozy Victorian in Quiet Residential Setting

La Grange
10.0 out of 10, Exceptional, (98)
"Beautiful, quiet, historic yet modern!!"
United States
Amanda K.
The price is ￥22,783
￥35,764 total
includes taxes & fees
Nov 10 - Nov 11
Charming & Cozy Victorian in Quiet Residential Setting
TV, offices
Windy Hill Retreat | Modern Farmhouse with Views, Cowboy Pool & Firepit

Windy Hill Retreat | Modern Farmhouse with Views, Cowboy Pool & Firepit

2.0 star property
La Grange
10.0 out of 10, Exceptional, (1)
"My overall impression of our recent stay at your modern farmhouse was truly a delightful experience for my family and me. From the moment we arrived, we were captivated by the beautiful views that surround the property. The modern farmhouse is situated on serene acreage, offering a peaceful and tranquil environment that was just perfect for our getaway.  The fully equipped kitchen made it a breeze to prepare our meals, and we thoroughly enjoyed spending time on the great deck, which provided a...
United States
Jocelyn W.
Windy Hill Retreat | Modern Farmhouse with Views, Cowboy Pool & Firepit
Terrace/patio
Pinehaven Luxury Glamping

Pinehaven Luxury Glamping

La Grange
10.0 out of 10, Exceptional, (48)
"The property matched the pictures. It was a unique venue and very well thought out. Plenty of nice touches. Would definitely come bask"
United States
Anthony T.
The price is ￥17,812
￥26,828 total
includes taxes & fees
Nov 10 - Nov 11
Pinehaven Luxury Glamping
Private kitchen
Adorable Guest Cabin In The Woods

Adorable Guest Cabin In The Woods

La Grange
9.8 out of 10, Exceptional, (63)
"The cozy cabin is a great spot for us to stay for our visits back to see family and the surrounding property is beautiful."
United States
Heather G.
The price is ￥12,289
￥19,348 total
includes taxes & fees
Nov 10 - Nov 11
Adorable Guest Cabin In The Woods
Living area
Round Top Refuge Main House

Round Top Refuge Main House

2.0 star property
La Grange
10.0 out of 10, Exceptional, (3)
"Charming and comfortable!"
United States
Devan M.
The price is ￥25,314
￥48,772 total
includes taxes & fees
Nov 12 - Nov 13
Round Top Refuge Main House
Property grounds
Cozy Cottage With a View in La Grange

Cozy Cottage With a View in La Grange

La Grange
10.0 out of 10, Exceptional, (8)
The price is ￥13,808
￥22,584 total
includes taxes & fees
Nov 10 - Nov 11
Cozy Cottage With a View in La Grange
Fridge, microwave, oven, stovetop
The Top @ Round Top + Escape to the country!

The Top @ Round Top + Escape to the country!

Round Top
10.0 out of 10, Exceptional, (28)
"We had a great time at this property! It is so close to town, very spacious and the check in process was so easy! We will definitely be back."
United States
Madison M.
The Top @ Round Top + Escape to the country!
Exterior
Waterfront Smithville River House

Waterfront Smithville River House

Smithville
9.8 out of 10, Exceptional, (63)
"Great little place, quiet, serene and clean."
United States
James K.
Waterfront Smithville River House
Interior
Riverside Romance/Luxury RV/Starry Skies & S'mores

Riverside Romance/Luxury RV/Starry Skies & S'mores

Smithville
10.0 out of 10, Exceptional, (63)
"Great time!"
United States
cathy v.
The price is ￥10,433
￥25,232 total
includes taxes & fees
Nov 10 - Nov 11
Riverside Romance/Luxury RV/Starry Skies & S'mores
Smart TV, fireplace, video games, DVD player
Angeltom Cabin & RV:20 Acre Woods - >16 pip + Jacuzzi + treehouse + UTV + 2ponds

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

La Grange
10.0 out of 10, Exceptional, (107)
"This place was great, plenty to do! Plenty of fun all around! No problems with ac or anything house wise. The 13 of us stayed comfortably and had lots of fun grilling and catfishing on the dock. Hope to be back!"
United States
Alyssa D.
Angeltom Cabin & RV:20 Acre Woods - >16 pip + Jacuzzi + treehouse + UTV + 2ponds
Fridge, microwave, oven, stovetop
Short cottage

Short cottage

2.0 star property
Downtown Smithville
9.4 out of 10, Exceptional, (9)
"Nice property. Close to downtown. Comfortable and clean"
United States
Kevin B.
Short cottage
Pool
Casa Tres Hermanas | Pool+Hot Tub+Fire Pit+Grill

Casa Tres Hermanas | Pool+Hot Tub+Fire Pit+Grill

Round Top
9.8 out of 10, Exceptional, (22)
"Lovely property! Easy for groups- 2 Primary suites downstairs, fun sleepover space upstairs, and a wonderful private bedroom in the garage area with accessible bathroom. Worked perfectly for our group of designers."
United States
Juliana E.
Casa Tres Hermanas | Pool+Hot Tub+Fire Pit+Grill
Property grounds
Escape to Giddings - Charming 2-Bedroom Vacation Home

Escape to Giddings - Charming 2-Bedroom Vacation Home

Giddings
10.0 out of 10, Exceptional, (140)
"Great place to get away. Close to everything and feels like you’re in the middle of nowhere. "
United States
Quincy W.
Escape to Giddings - Charming 2-Bedroom Vacation Home
Coffee/tea maker, cookware/dishes/utensils
Enchanting Casita, 5 minutes to Round Top!

Enchanting Casita, 5 minutes to Round Top!

Fayette County
9.8 out of 10, Exceptional, (64)
"Our desire was to have a quiet, comfortable little house close to Round Top and Enchanting Casita was advertised to be just what we wanted. The grounds were very pretty and the location was great. Negatives were the place was not very clean. The porch was not swept and the outdoor furniture was not really inviting. We had a lot of little black bugs in the bathroom and a few in our bed. The bed was very comfortable and the shower was nice."
United States
Mary L.
The price is ￥15,189
￥29,897 total
includes taxes & fees
Nov 10 - Nov 11
Enchanting Casita, 5 minutes to Round Top!
1 bedroom, free WiFi, bed sheets
Charming Cottage, 5 Minutes to Round Top!

Charming Cottage, 5 Minutes to Round Top!

Round Top
9.0 out of 10, Wonderful, (2)
"Great stay. Second time to stay on this property and both houses were great."
United States
Anonymous traveler
The price is ￥14,575
￥29,204 total
includes taxes & fees
Nov 10 - Nov 11
Charming Cottage, 5 Minutes to Round Top!
Pool
Fun, eclectic Round Top home w/POOL! 5 min to town

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

Fayette County
9.8 out of 10, Exceptional, (89)
"We truly enjoyed staying at this property. It was perfect for us. The house is charming and private. It was in an ideal location to do our antiquing and be able to come back to rest and then go out for dinner."
United States
Sarah M.
The price is ￥45,873
￥90,652 total
includes taxes & fees
Nov 10 - Nov 11
Fun, eclectic Round Top home w/POOL! 5 min to town
Terrace/patio
Sleep 40+ Lakeside Retreat on 53 Acre Ranch

Sleep 40+ Lakeside Retreat on 53 Acre Ranch

La Grange
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!"
United States
Cherise B.
Sleep 40+ Lakeside Retreat on 53 Acre Ranch
Fridge, microwave, oven, stovetop
Charming Victorian Bike to Shops, Mins to Antiques & Wedding Venues

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

La Grange
10.0 out of 10, Exceptional, (56)
"The attention to detail was great and the short distance to our wedding venue made everything seamless. A beautiful property, we very much enjoyed our stay."
United States
Patrick R.
Charming Victorian Bike to Shops, Mins to Antiques & Wedding Venues
Fridge, microwave, oven, dishwasher
Designory Round Top home, scenic views & pond!

Designory Round Top home, scenic views & pond!

Round Top
10.0 out of 10, Exceptional, (6)
"We came to Warrenton for a concert at the Round Top Festival Hill. This home is perfect for 2 couples, with each room allowing privacy. The home was clean and well-stocked. The decor is lovely! Would stay here again! "
United States
Stephanie A.
The price is ￥35,747
￥78,135 total
includes taxes & fees
Nov 18 - Nov 19
Designory Round Top home, scenic views & pond!
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

Studio 6 – Giddings, Tx

Studio 6 – Giddings, Tx

10/10 Excellent
"Clean, fast check in"
Nicole D Berrios 1-night trip
Posted 3 days ago
Studio 6 – Giddings, Tx

Find out more about Winchester

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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?

Charming & Cozy Victorian in Quiet Residential Setting: You might want to consider this vacation home rental near Winchester, which offers a garden, a selection of books, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.