Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Hunter/Fisherman/Horse Friendly, Small Family Friendly
9.8 out of 10, Exceptional, (47)
"Alice was fantastic, great stay as advertised. Wish it had a queen instead of full but still highly recommend."
United States
Agustin A.
The price is €141
includes taxes & fees
2 Nov - 3 Nov
Hunter/Fisherman/Horse Friendly, Small Family Friendly
The Western Roost | A Vensérra Retreat Near Hot Springs State Park
8.4 out of 10, Very good, (5)
"Great stay"
United States
Maria G.
The price is €187
includes taxes & fees
2 Nov - 3 Nov
The Western Roost | A Vensérra Retreat Near Hot Springs State Park
This home is a great spot to stash your belongings and go explore the historical town of Thermopolis
9.2 out of 10, Wonderful, (57)
"Came for our grandson's football game. Good location. We could hear crickets. The back yard was great for our 11 lb. Dog. Would stay again."
United States
Barbara
The price is €153
includes taxes & fees
2 Nov - 3 Nov
This home is a great spot to stash your belongings and go explore the historical town of Thermopolis
A home away from home.
9.4 out of 10, Exceptional, (117)
"The property was very nice and Jerry was very attentive and communicative throughout the process. "
United States
Tracey S.
The price is €143
includes taxes & fees
1 Dec - 2 Dec
A home away from home.
Charming 1-bedroom apartment with WiFi, AC in quaint Thermopolis
10.0 out of 10, Exceptional, (6)
"This little attic studio was a fabulous place to stay! Clean, quiet, and so comfortable. Temparpedic mattress, soft cozy couch, and a full kitchen. Shower is small, and be super careful with the curtain so you don't flood the bathroom! This is now our favorite VRBO to date! Our host was very wonderful, and had great suggestions for local attractions. Wish I could give more than 5 stars!!"
United States
Barbara
The price is €127
includes taxes & fees
8 Nov - 9 Nov
Charming 1-bedroom apartment with WiFi, AC in quaint Thermopolis
Furnished with a western decor and many antiques, yet has modern amenities.
9.6 out of 10, Exceptional, (89)
"Super clean, comfortable & thoughtful extras! Quiet neighborhood & great accomodations made for a very relaxing stay. "
United States
Dawn H.
The price is €153
includes taxes & fees
11 Nov - 12 Nov
Furnished with a western decor and many antiques, yet has modern amenities.
Copper Winds Private Cabin on 6 Acres
10.0 out of 10, Exceptional, (17)
"We had a lovely stay. Sunset shining on the cliffs was stunning. We experienced exceptional hospitality with wonderful hosts. "
United States
Janine Y.
The price is €238
includes taxes & fees
2 Nov - 3 Nov
Copper Winds Private Cabin on 6 Acres
This house is a 3 bedroom(s), 1 bathrooms, located in Thermopolis, WY.
9.0 out of 10, Wonderful, (35)
"Perfect location for the family to meet and so much to do nearby. Our grandson wants this to be our annual vacation home! Thanks so much for the care and consideration made available! "
United States
Diane
The price is €234
includes taxes & fees
11 Nov - 12 Nov
This house is a 3 bedroom(s), 1 bathrooms, located in Thermopolis, WY.
A Charming 100+ year old vintage farmhouse that has been updated with modern amenities.
10.0 out of 10, Exceptional, (2)
"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 €257
includes taxes & fees
3 Nov - 4 Nov
A Charming 100+ year old vintage farmhouse that has been updated with modern amenities.
Cozy Cabin in Thermopolis. Pet Friendly!
10.0 out of 10, Exceptional, (4)
"Beautiful little place to stay. If you're fishing the river the boat ramp is a few minutes away. "
United States
Brian B.
The price is €227
includes taxes & fees
7 Nov - 8 Nov
Cozy Cabin in Thermopolis. Pet Friendly!
❤Weekday Fishing Rates, Couples, Families Love Us. Location, Amenity-Rich, Pets
10.0 out of 10, Exceptional, (48)
"Great place. Host is second to none. Second year staying here and will be back next year! "
United States
Matt F.
The price is €430
includes taxes & fees
2 Nov - 3 Nov
❤Weekday Fishing Rates, Couples, Families Love Us. Location, Amenity-Rich, Pets
The Eagle's Nest is an oilfield building converted into a beautiful house right on the river.
9.6 out of 10, Exceptional, (34)
"Great spot to stay for a fishing trip. "
United States
Tim E.
The price is €345
includes taxes & fees
30 Nov - 1 Dec
The Eagle's Nest is an oilfield building converted into a beautiful house right on the river.
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

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, apart-hotels, 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 €127 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

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?

Just steps away from the Big Horn River: This holiday home rental outside of Winchester offers a balcony, a garden and a BBQ to help you feel perfectly comfortable 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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. Hot Springs State Park and Hot Springs State Park Bath House 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.