Vacation rentals in Upton

4.89 out of 5 average rating, 586 reviews

Tent in Devils Tower

Crazy Horse (14' tipi)

Crazy Horse & Custer traveled this way to Devils Tower. This tipi can comfortably sleep 4 adults. Each tipi has as two burner stove, 3 gallons of water, a pot, coffee fixing things, a propane lantern and a solar lantern. There is no electricity on the property and an outdoor solar shower available if desired. Sleeping places (pad, sheets, blankets and pillows) can be set up for a total fee of $30 for 4 payable on arrival; more available for $10. Please request this when making a reservation.

4.95 out of 5 average rating, 98 reviews

Cabin in Sundance

Kara Creek Ranch - Log Cabin

Looking to get away from it all? This cozy log cabin sits alone on a rise overlooking fields of sunflowers, where the deer & antelope graze and Kara Creek runs lazily through the valley. Guests are welcome to hike, fish Kara Creek, or fish the 11 acre pond stocked with trout (many over 20 inches) and large mouth bass. This cabin sits about 4 miles from our ranch headquarters, where we also offer food, horseback riding and other activities from May-Oct. Please contact us for more information!

4.9 out of 5 average rating, 29 reviews

Apartment in Sundance

Black Hills Gateway Get-Away!

Relax at the gateway to the Black Hills in the beautiful Bear Lodge Mountains! This private entry apartment located on a small farm minutes from I-90 in Wyoming is perfect for the entire family. Take in the sights of the Black Hills, and then getaway for some peace , quiet, and great views! Hunters, travelers, bikers, hikers-- all like are welcome here! On-suite exercise gym included. Beautiful views and friendly folks here. Message to inquire about horse accommodation layover options.

4.95 out of 5 average rating, 107 reviews

Charming Cabin in Pine Haven

- 2 bedrooms and 2 bathrooms, sleeps up to 8 - Wifi throughout - Parking for 3 vehicles - Washer / Dryer - On quiet street - 10 minutes from Key Hole marina - Close to Devils Tower, about 40 miles * No smoking permitted on the property. * No pets * Please alert us ahead of your arrival if you plan to use the futon beds. * Sturgis week available. Nightly price of $400 with a minimum 4 nights. * Winter reservations are subject to cancellations due to problems with snow removal/availability.

4.87 out of 5 average rating, 77 reviews

Pine Haven, WY home viewing Keyhole Reservoir

Experience life in the heart of Pine Haven!! Golf club ,Keyhole Reservoir & State Park. Two restaurant bars in 2 minutes walking distance. Playground, volleyball , pickle ball court. Enjoy Wi-Fi, two smart TVs, clean linens, toiletries, laundry, a well stocked kitchen, Gas BBQ, wrap around deck, large driveway. Friendly location with fishing; Visit nearby Devil's Tower, Deadwood, Sturgis memorable sunrise on the deck;2 bicycles, 4 kayaks, a paddle board, corn hole lawn and card games ..

5 out of 5 average rating, 14 reviews

Cabin in Sundance

Cabin - Black Hills of Wyoming

Relax with the whole family in the tranquil & peaceful beauty of the Black Hills of Wyoming. Enjoy scenic views from the deck, nearby hiking & mountain biking trails, wildlife, and proximity to Black Hills attractions - Deadwood, Devils Tower…. Located 60 miles from Gillette WY & Sturgis SD. The kids can enjoy playing in the fort or swinging from the tree swing. Ideal location for hunting and fishing. Strong cell service. TV DVD VCR ROKU(using Hot Spot). Pet friendly, non-smoking cabin.

4.98 out of 5 average rating, 622 reviews

Loft in Lead

Harley Court Loft

Cozy loft in the Lead, SD. Moments from downtown, but secluded. Minutes to outdoor activities, skiing, snowshoeing, hiking, biking, or snowmobiling. Winter months, all wheel / 4 wheel drive vehicle is a must!! Close to restaurants, brew pub, and night life!! Kitchenette with microwave, coffee maker, toaster, hot plate, (with pans), and small frig. The loft has electric heat and portable AC. There are 18 steps to get to the loft, for two people. No pets accepted!

Tiny home in Four Corners

4.98 out of 5 average rating, 161 reviews

KK, tiny cabin close to beauty of Black Hills SD

A 10 x 32 tiny cabin conveniently located 1 mile off paved Hwy 585. Our working ranch has cattle, goats, horses. Beautiful scenery with frequent sightings of elk, deer, turkeys. This unique cabin features: WIFI, TV with DVD player only, microwave, retro fridge, bathroom with shower, twin bunk beds, and a queen bed. Experience the beauty and serenity of Wyoming and closeness of Black Hills attractions; and simple ranch life! Quiet and off the grid. Beautiful sunsets, too.

4.98 out of 5 average rating, 89 reviews

Tiny home in Lead

Mirror Cabin in the Black Hills

You'll love this unique and romantic escape. This tiny mirror cabin, REFLECT+RECONNECT, is nestled in the serene beauty of the Black Hills of South Dakota. It creates a rejuvenating and memorable experience. This unique retreat is designed to offer you a chance to disconnect from the hustle and bustle of everyday life and reconnect with the special person in your life, yourself, and the surrounding nature.

4.96 out of 5 average rating, 291 reviews

Apartment in Custer

Journeys End cozy Apartment attached to house

Cozy apartment attached to the main house, queen bed, full sized couch bed, large shower, mini kitchen with sink, microwave, refrigerator, coffee pot, toaster. Deck outside--gas grill and patio furniture. Located on 26 acres of pine forest, meadow and mt. Rock shop on property. Lots of space for rest, relaxation, or hiking. Access to children's playground, mountaintop deck and hiking trails.

Superhost

Home in Hulett

4.7 out of 5 average rating, 271 reviews

Your gateway to Devils Tower, Biker Rally, Hunting

Hulett is a small town, and everything is within a half mile. This includes the grocery store, two cafes, bank, hardware store, and two bars. There is a fancy steakhouse at the golf course. The town library is just across the street. Devils Tower is about 15 miles away. You can easily visit Mt. Rushmore and the Crazy Horse memorial in a day trip, and come back to a quiet and comfortable evening.

4.89 out of 5 average rating, 27 reviews

Cabin in Pine Haven

Cabin 1 @ Empire Lodge

Relax with the whole family at this peaceful and rustic cabin. Simple and quaint. Nestled in beautiful Pine Haven, Wyoming, this cabin is only minutes from Keyhole Reservoir and right down the road from Devils Tower. This cabin features a queen-sized bed with a roll-away, a ¾ bath and a small kitchenette. Coin-Op laundry is available on site.

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Other great vacation rentals in Upton

Apartment in Moorcroft

Studio Suite Apartment #9 in Moorcroft Wyoming

StevenRating, 5 stars1 week ago

always responsive to my texts in a timely manner and addressed any issues I brought up

4.88 out of 5 average rating, 272 reviews

Hotel room in Moorcroft

Old Corner Sunrise Room

KevinRating, 5 stars2 weeks ago

Robert has organised the whole thing really well. He takes care of all the detail. Hotel level accommodation.

5 out of 5 average rating, 7 reviews

Camper/RV in Aladdin

Chase's Farmyard

ColtraRating, 5 stars1 day ago

Absolutely beautiful place to relax! This is a great get away for someone looking to find some peace in nature. The camper has everything you need to be comfortable. If you’re looking for “convenience” this is a bit out of the way on a dirt road without any grocery stores or restaurants nearby. The host may have some eggs and baked goods for purchase. Our only regret was not planning a longer stay to really take advantage of how relaxing and serene the land is.

5 out of 5 average rating, 6 reviews

Bedbox and Beyond

JacquelineRating, 5 stars4 months ago

We loved this place! It's cozy, has little extras that were useful when traveling, abundant wildlife right outside the windows, super kid friendly. This checked so many boxes and was so relaxing. Loren was great! Very responsive and friendly. This place is settled at the end of a caldasac in a treed area. Close enough to amenities and yet far enough away to be private and quiet. So many turkeys and deer wandering right in the front and back yard, the kids loved it. kids rooms were great, lots of new books that everyone enjoyed.

4.89 out of 5 average rating, 18 reviews

Cheerful 3 bedroom close to Keyhole!

KirsiRating, 5 stars1 month ago

This is a beautiful home. It’s welcoming as soon as you walk in. Lots of windows to see the scenery. It’s just like the pictures and even better! I enjoyed sitting on the porch with my coffee and breakfast waiting for the sun to rise over the trees. Then in the evening, we sat on the back deck. What a lovely home!

4.93 out of 5 average rating, 30 reviews

Camper/RV in Custer

Quite RV Stay In National Forest

BeckyRating, 5 stars3 days ago

This unique Airbnb was amazing in so many ways, starting with Alicia and Derek, the lovely and welcoming hosts. The surroundings couldn’t be more beautiful and private. The drive in is breathtaking and on an extremely well maintained gravel road. The friendly animals on Derek and Alicia’s country ranch are a bonus. Such a wonderful and economical place to stay when visiting Custer!