Winchester Vacation Rentals from ￥27,906: Search Short-Term Rentals

Q: What's the top vacation rental in Winchester?

Walk to Lake + Stock Tank Pool + Fire Pit : Visitors like this Winchester vacation home rental. It is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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Our top choices for Winchester vacation rentals

A compact, rustic cabin interior with a loft bedroom, a dining area with a table set for two, and a TV mounted on the wall.

1. Dodo's Place - Tiny Home on 22 Acres

Smithville

Law

￥30,297 total

includes taxes & fees

Oct 21 - Oct 22

A cabin with a deck, outdoor seating, and a view of a forest.

2. Cozy Studio Cottage on 22 Acres

Smithville

Jim C.

￥24,399 total

includes taxes & fees

Oct 15 - Oct 16

A living room with a blue sofa, wooden coffee table, and a television on a wooden cabinet.

3. Spacious MCM home 2 minutes from downtown, Pet-Friendly!

Smithville

Catherine K.

￥55,547 total

includes taxes & fees

Nov 1 - Nov 2

A view of a lake with surrounding greenery and a clear sky.

4. Cozy Cottage With a View in La Grange

La Grange

Leeann

￥25,016 total

includes taxes & fees

Oct 20 - Oct 21

A modern two-story house with a stone facade, a large garage, and a well-maintained lawn.

5. The best stay in Bastrop Texas

Bastrop

A single-story house with a front porch, a red door, and a small staircase leading to the entrance.

6. Boutique Retreat Minutes From Round Top!

Fayetteville

￥107,537 total

includes taxes & fees

Oct 20 - Oct 21

A living room with a sofa, a bed, a dining area, and a kitchen.

7. Lost Pines Lake House near Bastrop State Park and Buescher State Park..

Smithville

Aleksandra L.

￥37,357 total

includes taxes & fees

Oct 26 - Oct 27

A covered porch with a wicker sofa, hanging plants, and a view of the yard.

8. Charming 3-bedroom house with AC in La Grange with Wrap around porches.

La Grange

Aundrea G.

￥90,663 total

includes taxes & fees

Oct 20 - Oct 21

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Top Winchester Hotel Reviews

Walk to Lake + Stock Tank Pool + Fire Pit

10/10 Excellent

"We had a wonderful stay at this property. The property was very clean and the beds were comfortable. Everyone enjoyed the hammocks and looking up at the tall pines. There were deer that came by in the morning. It was a very convenient walk or short drive to nearby Bastrop Lake where there are trails and fun activities. It was also close to downtown Bastrop. Sara was a responsive and helpful host. Highly recommend!"

Best Western Giddings Inn & Suites

8/10 Good

"The staff was friendly and helpful. The room was clean but there was a blinking bulb, I called the front desk and it was fixed within 20 minutes. The breakfast was adequate but I missed it on my first morning because it was only served 6-8 am and I had no reason to get dressed and moving until 8:30 am. The hours were much shorter than any other hotel I have stayed in."

The Elf's Aerie Treehouse, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire

10/10 Excellent

"Absolutely beautiful space. The design, the atmosphere, and the amenities were all amazing. Couldn't have asked for better communication with the host throughout the entire process of booking and the stay. 10/10 recommend for a time to when you need to just get away for a bit."

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

10/10 Excellent

"Secluded family vacation for those who enjoy their privacy. Rental was too big to explore in such a short time. Hosts were friendly and eager to make stay as pleasant as possible."

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?

Walk to Lake + Stock Tank Pool + Fire Pit: Visitors like this Winchester vacation home rental. It is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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 Tejas Lake. In the larger area, you’ll find Bluff Creek Ranch and Texas Wendish Heritage Museum.

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.

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Check prices for these dates

Our top choices for Winchester vacation rentals

1. Dodo's Place - Tiny Home on 22 Acres

2. Cozy Studio Cottage on 22 Acres

3. Spacious MCM home 2 minutes from downtown, Pet-Friendly!

4. Cozy Cottage With a View in La Grange

5. The best stay in Bastrop Texas

6. Boutique Retreat Minutes From Round Top!

7. Lost Pines Lake House near Bastrop State Park and Buescher State Park..

8. Charming 3-bedroom house with AC in La Grange with Wrap around porches.

9. Bridal Ready + Southern Charm | The Moli

10. Charming & Cozy Victorian in Quiet Residential Setting

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

12. Modern Retreat in the Pine Forest of Bastrop, minutes from Space X

13. Relax & Recharge in Paige, Tx - 15 Acres, Fishing, and Farm Animals Await

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

15. Site 3 Private camp power @ site w Hot Showers & Potty At The CommunityBathhouse

16. Romance Glamping | Pup Paradise | Near River | ADA

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

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

19. Swiss Alp Texas Cabin

20. TuscanyNTexas

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

Walk to Lake + Stock Tank Pool + Fire Pit

The Oak Motel

Executive inn & Suites

Country feel in this open plan 3 bed/2 bath home.

River Valley Motor Inn

Best Western La Grange Inn & Suites

Best Western Giddings Inn & Suites

The Elf's Aerie Treehouse, An Enchanting Dog-Friendly Treehouse in the Lost Pines Shire

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

Find out more about Winchester

Frequently asked questions

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