Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

Hunter/Fisherman/Horse Friendly, Small Family Friendly

Hunter/Fisherman/Horse Friendly, Small Family Friendly
Worland
9.8 out of 10, Exceptional, (49 reviews)
"Quiet, cozy cabin with great kitchen amenities. Comfy beds, and great hosts. Horses and cranes were a treat. Great jump off spot to explore Wyomings abundant cultural, natural & historical sites. "
United States
Jean U.
The price is AU$248
includes taxes & fees
15 Feb - 16 Feb
Hunter/Fisherman/Horse Friendly, Small Family Friendly

Dog friendly with fenced in back yard Peaceful cabin with AC in charming Worland

Dog friendly with fenced in back yard Peaceful cabin with AC in charming Worland
Worland
9.6 out of 10, Exceptional, (4 reviews)
"It was a great place to stay for me and my dog."
United States
Weston W.
The price is AU$162
includes taxes & fees
15 Feb - 16 Feb
Dog friendly with fenced in back yard Peaceful cabin with AC in charming Worland

NEW! The Anglers Nook, The Fish House

NEW! The Anglers Nook, The Fish House
Thermopolis
The price is AU$651
includes taxes & fees
15 Feb - 16 Feb
NEW! The Anglers Nook, The Fish House

We are located just south of Thermopolis on the Big Horn river

We are located just south of Thermopolis on the Big Horn river
Thermopolis
9.2 out of 10, Wonderful, (42 reviews)
"Had a nice place for our family to stay. Very friendly owner and helpful"
United States
Steve & Katie E.
The price is AU$327
includes taxes & fees
15 Feb - 16 Feb
We are located just south of Thermopolis on the Big Horn river

❤Weekday Fishing Rates, Couples, Families Love Us. Location, Amenity-Rich, Pets

❤Weekday Fishing Rates, Couples, Families Love Us. Location, Amenity-Rich, Pets
Thermopolis
10.0 out of 10, Exceptional, (49 reviews)
"Great location "
United States
Mary U.
The price is AU$602
includes taxes & fees
17 Feb - 18 Feb
❤Weekday Fishing Rates, Couples, Families Love Us. Location, Amenity-Rich, Pets

Copper Winds Private Cabin on 6 Acres

Copper Winds Private Cabin on 6 Acres
Thermopolis
9.8 out of 10, Exceptional, (23 reviews)
"VeryPeaceful and Beautiful cabin stay"
United States
MEREDEITH A.
The price is AU$380
includes taxes & fees
16 Feb - 17 Feb
Copper Winds Private Cabin on 6 Acres

Charming 1-bedroom apartment with WiFi, AC in quaint Thermopolis

Charming 1-bedroom apartment with WiFi, AC in quaint Thermopolis
Thermopolis
10.0 out of 10, Exceptional, (6 reviews)
"Very well kept..the shower was kinda small but worked out."
United States
David K.
The price is AU$203
includes taxes & fees
20 Feb - 21 Feb
Charming 1-bedroom apartment with WiFi, AC in quaint Thermopolis

Furnished with a western decor and many antiques, yet has modern amenities.

Furnished with a western decor and many antiques, yet has modern amenities.
Thermopolis
9.6 out of 10, Exceptional, (89 reviews)
"Great location, excellent communication and just perfect for a weekend of fishing!"
United States
Melissa A.
The price is AU$245
includes taxes & fees
16 Feb - 17 Feb
Furnished with a western decor and many antiques, yet has modern amenities.

This house is a 3 bedroom(s), 1 bathrooms, located in Thermopolis, WY.

This house is a 3 bedroom(s), 1 bathrooms, located in Thermopolis, WY.
Thermopolis
9.0 out of 10, Wonderful, (39 reviews)
"Great spot for a fishing weekend! "
United States
Lisa T.
The price is AU$395
includes taxes & fees
15 Feb - 16 Feb
This house is a 3 bedroom(s), 1 bathrooms, located in Thermopolis, WY.

The Western Roost | A Vensérra Retreat Near Hot Springs State Park

The Western Roost | A Vensérra Retreat Near Hot Springs State Park
Thermopolis
8.4 out of 10, Very good, (5 reviews)
"Great stay"
United States
Maria G.
The price is AU$298
includes taxes & fees
20 Feb - 21 Feb
The Western Roost | A Vensérra Retreat Near Hot Springs State Park

A newly renovated home full of fun games for the entire family to enjoy.

A newly renovated home full of fun games for the entire family to enjoy.
Thermopolis
9.8 out of 10, Exceptional, (22 reviews)
"Loved that we could bring our dog as we explored the area!"
United States
Lori W.
The price is AU$460
includes taxes & fees
16 Feb - 17 Feb
A newly renovated home full of fun games for the entire family to enjoy.

The Eagle's Nest is an oilfield building converted into a beautiful house right on the river.

The Eagle's Nest is an oilfield building converted into a beautiful house right on the river.
Thermopolis
9.6 out of 10, Exceptional, (34 reviews)
"Great spot to stay for a fishing trip. "
United States
Tim E.
The price is AU$529
includes taxes & fees
22 Feb - 23 Feb
The Eagle's Nest is an oilfield building converted into a beautiful house right on the river.

A Charming 100+ year old vintage farmhouse that has been updated with modern amenities.

A Charming 100+ year old vintage farmhouse that has been updated with modern amenities.
Thermopolis
10.0 out of 10, Exceptional, (8 reviews)
"We loved the charm of this vintage home! We had everything we needed, space, beds, bathrooms etc. Such a fun rental. We would definitely stay here again. "
United States
KELLY F.
The price is AU$403
includes taxes & fees
15 Feb - 16 Feb
A Charming 100+ year old vintage farmhouse that has been updated with modern amenities.
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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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 favourite 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 depend 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 AU$245 per night. Entering your travel dates in the search wizard might find you 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

Are there holiday rentals 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?

❤Weekday Fishing Rates, Couples, Families Love Us. Location, Amenity-Rich, Pets: This holiday home rental outside of Winchester is located on a river, and has an outdoor pool, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Winchester?

Explore the area and family-friendly sights such as Wyoming Dinosaur Center, or get out into nature at a spot like Bighorn River. Roundtop Mountain and Hot Springs State Park are a couple of places you'll find in the wider area.

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 feature amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.