
Roosevelt County Vacations & Trips from $436
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Your Roosevelt County Vacation
Answer the call of adventure with a customized vacation package to Roosevelt County. Wherever it is you're going and whatever you have planned, get ready to discover a destination that'll make you feel alive. A trip to Roosevelt County promises lots to see and do. Not sure where to start? Wolf Point is one of the most popular places to stay here. If you're ready to stop dreaming and start discovering, Expedia will help turn your Roosevelt County vacation into reality.
Top destinations in Roosevelt County

Wolf Point

Culbertson
The Latest Roosevelt County Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Lone Tree Inn
Price was $526, price is now $436 per person
$436
per person
Aug 21 - Aug 25
found 7 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sidney (SDY)
7.6/10 Good! (256 reviews)
Well, when you first pull up, there’s a couple of the bottom Hotel windows open with rolls of carpet and garbage hanging out of them as if they were in the middle of doing some remodels but then stopped. Went inside no Hotel staff used the phone at the front desk for them to tell me my key was laying there in a plastic container. Garbage was overflowing outside inside room could have used a good cleaning. Looks as though they may be just changed the sheets, younger teens I believe staying in a room there cause I saw them at night and in the morning knocking on windows in the parking lot I did not see anything set out for breakfast. Except some cold cereal. I reserved a king size bed with confirmation and got two queens and what looked like a piece of a condom was on the floor hanging out from underneath one of the beds.
Reviewed on Jun 21, 2026

Microtel Inn & Suites by Wyndham Sidney
Price was $546, price is now $464 per person
$464
per person
Aug 21 - Aug 25
found 7 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sidney (SDY)
8.2/10 Very Good! (433 reviews)
Staff was helpful.. laundry was backed up so no fresh towels were available..
Reviewed on Jun 30, 2026

Wingate by Wyndham Sidney
Price was $880, price is now $766 per person
$766
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Sidney (SDY)
8.8/10 Excellent! (443 reviews)
While the room was clean, the shower head was clogged and didn't work well. We had 3 guests with only 2 towels, so as I searched for another towel, I had to help myself to one in the laundry room because no one was at the desk for a long period of time. The ice machine didn't work, and when the young man did return to the desk, he told me to just go into the pantry and grab some (incredibly unsanitary!). The young lady who checked us in was incredibly friendly and helpful.
Reviewed on Jul 10, 2026

The Roosevelt Hotel & RV Park Gateway to Theodore Roosevelt National Park-Medora-on i-94
Price was $588, price is now $520 per person
$520
per person
Aug 21 - Aug 25
found 7 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Sidney (SDY)
6.8/10 (41 reviews)
Room door already opened, beds unmade, trash in rooms. Most room doors open showing filthy conditions. The staff was in a very heated argument when I arrived. Do not stay there under any circumstances. I'd sleep in the car before this place.
Reviewed on Jul 9, 2026
Find the Best Roosevelt County Vacation Packages
Roosevelt County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | L. M. Clayton Airport (OLF) |
Top Sights | Nellie’s Park and Firehall Park |
Roosevelt County Hotel Deals

Homestead Inn Wolf Point Hwy 2
101 Highway East Wolf Point MT
Fully refundable
$125 nightly
The price is $135 total per night from Jul 13 to Jul 14
$135 total
Jul 13 - Jul 14
Total with taxes and fees
7.8/10 Good! (368 reviews)
"It’s a good place to stay during our long trip to Yellowstone."
Reviewed on Jul 10, 2026

Homestead Inn Extended Stay - 3 nights minimum
6201 A N 1 Dr Wolf Point MT
Fully refundable
$89 nightly
The price is $96 total per night from Jul 12 to Jul 13
$96 total
Jul 12 - Jul 13
Total with taxes and fees
8/10 Very Good! (1 review)
"I'm originally from the area. It's been some years since I've been back. I am shocked at the change. I am surprised how clean and quiet this motel was. It was worth the value. I would definitely stay again. I had no problems while staying here. The sink was leaking but I showed the housekeeper. The ..."
Reviewed on Oct 1, 2025

Homestead Inn Extended Stay - 3 nights minimum
Wolf Point MT
6/10 (2 reviews)
"Bed bugs! I was refunded but NOT a full refund. I was bitten up the 1st night I arrived. I arrived in the evening & wasn't feeling well either. I paid for 3-4 days but was ASKED to checkout during my illness. I flew out thereafter. This used to be a very nice building. I stayed here in the past. ..."
Reviewed on Jun 26, 2026
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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