Holiday Rentals in Hillsdale

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Our top choices for Hillsdale holiday rentals

Ayu Ranch | Panoramic views | Hot tub

Ayu Ranch | Panoramic views | Hot tub
Cheyenne
9.6 out of 10, Exceptional, (4)
"great"
United States
Curt N.
The price is €486
includes taxes & fees
5 Jan - 6 Jan 2026
Ayu Ranch | Panoramic views | Hot tub

2 BDRM - Sleeps up to 6

2 BDRM - Sleeps up to 6
Cheyenne
9.0 out of 10, Wonderful, (54)
"Nice litttle place"
United States
Nancy R.
The price is €139
includes taxes & fees
10 Jan - 11 Jan 2026
2 BDRM - Sleeps up to 6

Private apartment in the center of Cheyenne

Private apartment in the center of Cheyenne
Cheyenne
8.4 out of 10, Very good, (35)
"Was a homey place to stay while visiting family."
United States
Lori P.
The price is €104
includes taxes & fees
1 Jan - 2 Jan 2026
Private apartment in the center of Cheyenne

1 BDRM - Great Location!

1 BDRM - Great Location!
Cheyenne
8.4 out of 10, Very good, (20)
"Good place, would be nice to have a small fenced in area for dogs"
United States
Michelle P.
The price is €110
includes taxes & fees
1 Jan - 2 Jan 2026
1 BDRM - Great Location!

Close - in Rural Studio - Great Star-gazing!

Close - in Rural Studio - Great Star-gazing!
Cheyenne
9.6 out of 10, Exceptional, (37)
"Great spot for an overnight stay somewhat close to the airport. "
United States
Rebecca H.
The price is €109
includes taxes & fees
30 Dec - 31 Dec
Close - in Rural Studio - Great Star-gazing!

Quiet Cozy Downtown Cheyenne

Quiet Cozy Downtown Cheyenne
Cheyenne
10.0 out of 10, Exceptional, (2)
"The photos and the housing look exactly the same. That was a great surprise!My husband and I stayed here for a quick visit during Thanksgiving. Luckily, the kitchen had everything and more that we needed to have a perfect dinner.The host was friendly and quickly responded when we had questions.The location was great! It is walkable to the downtown area and felt very safe.The bed is absolutely comfortable!This location also has a little yard for your dogs, which was greatly appreciated."
United States
Nicole J.
The price is €133
includes taxes & fees
7 Jan - 8 Jan 2026
Quiet Cozy Downtown Cheyenne

Enjoy relaxing comfort in this uniquely designed home - 5min from Frontier Park

Enjoy relaxing comfort in this uniquely designed home - 5min from Frontier Park
Cheyenne
9.8 out of 10, Exceptional, (75)
"This place was amazing we loved it all three of us walk have fun with all your beautiful and fun designs love it 💕"
United States
MeMe
The price is €163
includes taxes & fees
31 Dec - 1 Jan 2026
Enjoy relaxing comfort in this uniquely designed home - 5min from Frontier Park

The Tribe Space- Country, but close

The Tribe Space- Country, but close
Cheyenne
9.6 out of 10, Exceptional, (44)
"Location waa nice outside of town."
United States
Thy N.
The price is €118
includes taxes & fees
30 Dec - 31 Dec
The Tribe Space- Country, but close

Downtown Cheyenne Duplex

Downtown Cheyenne Duplex
Cheyenne
The price is €151
includes taxes & fees
18 Jan - 19 Jan 2026
Downtown Cheyenne Duplex

Capitol-Side • Downtown • Basement Pirate Themed

Capitol-Side • Downtown • Basement Pirate Themed
2.0 star property
Cheyenne
The price is €263
includes taxes & fees
25 Jan - 26 Jan 2026
Capitol-Side • Downtown • Basement Pirate Themed

Duplex close to downtown Cheyenne

Duplex close to downtown Cheyenne
Cheyenne
The price is €137
includes taxes & fees
7 Jan - 8 Jan 2026
Duplex close to downtown Cheyenne

Cozy RV with 2 sleeping areas & WiFi, AC in Cheyenne or your favorite camp site.

Cozy RV with 2 sleeping areas & WiFi, AC in Cheyenne or your favorite camp site.
2.0 star property
Cheyenne
The price is €222
includes taxes & fees
30 Dec - 31 Dec
Cozy RV with 2 sleeping areas & WiFi, AC in Cheyenne or your favorite camp site.

Indoor Pool + Hot Tub | Fully Equipped Suite

Indoor Pool + Hot Tub | Fully Equipped Suite
Cheyenne
The price is €153
includes taxes & fees
4 Jan - 5 Jan 2026
Indoor Pool + Hot Tub | Fully Equipped Suite

Cheyenne Blue Painted Lady

Cheyenne Blue Painted Lady
Cheyenne
10.0 out of 10, Exceptional, (6)
"House looked brand new as did all the furnishings. Owner responded to my questions within minutes. Would definitely stay again!"
United States
Kelli T.
The price is €412
includes taxes & fees
30 Dec - 31 Dec
Cheyenne Blue Painted Lady

Cozy Cottage Basement Apartment

Cozy Cottage Basement Apartment
Cheyenne
The price is €122
includes taxes & fees
18 Jan - 19 Jan 2026
Cozy Cottage Basement Apartment

Pet-Friendly Townhouse Located Near Frontier Park and the Capitol Building

Pet-Friendly Townhouse Located Near Frontier Park and the Capitol Building
Cheyenne
9.6 out of 10, Exceptional, (37)
"This is a wonderful place to stay. Kellie is a wonderful hostes. She has created a warm and welcoming place to stay. We would definitely stay here again."
United States
Monti H.
The price is €281
includes taxes & fees
4 Jan - 5 Jan 2026
Pet-Friendly Townhouse Located Near Frontier Park and the Capitol Building

Shotgun Blue

Shotgun Blue
Cheyenne
10.0 out of 10, Exceptional, (41)
"Great little house. Very clean, well stocked, and comfortable. Convenient location. Will definitely stay again if we are ever passing through! "
United States
talia f.
The price is €143
includes taxes & fees
31 Dec - 1 Jan 2026
Shotgun Blue

The Downtown Nest Cheyenne

The Downtown Nest Cheyenne
Cheyenne
The price is €110
includes taxes & fees
15 Jan - 16 Jan 2026
The Downtown Nest Cheyenne

Cheyenne Frontier Homes #2

Cheyenne Frontier Homes #2
Cheyenne
Cheyenne Frontier Homes #2

2 BDRM - Sleeps up to 6

2 BDRM - Sleeps up to 6
Cheyenne
8.4 out of 10, Very good, (38)
"Had to stay an extra day and they kindly accommodated us! Nice place. "
United States
Kiamichi L.
The price is €136
includes taxes & fees
3 Jan - 4 Jan 2026
2 BDRM - Sleeps up to 6
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 Hillsdale Hotel Reviews

Find out more about Hillsdale

Everything you need to know about Hillsdale 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 Hillsdale 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 Hillsdale holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Hillsdale holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillsdale. 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 Hillsdale 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 Hillsdale holiday rentals we have selected for you start as low as €104 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Hillsdale rentals

At Expedia, we put the best Hillsdale 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 Hillsdale 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 Hillsdale 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 Hillsdale. 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

Can I find holiday rentals in Hillsdale?

Yes, there are holiday rentals close to the most popular sights in Hillsdale, 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 Hillsdale has to offer?

Enjoy relaxing comfort in this uniquely designed home - 5min from Frontier Park: This holiday home rental outside of Hillsdale is located next to a golf course, and has a patio, a garden 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. You can relax into your holiday with a selection of games and 1 hot tub.

What can I see and do in Hillsdale?

Explore the area and family-friendly sights such as Wyoming Transportation Museum, or get out into nature at a spot like Cheyenne Botanic Gardens. In the wider area, you’ll find Frontier Square and Cheyenne Gunslingers.

What are holiday rentals like in Hillsdale?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Hillsdale. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.