Holiday rentals in Gregory

Cozy Little Getaway

*if calendar does not show availability for your desired dates please direct message me regarding availability Relax with the whole family at this peaceful place to stay. Great location, centrally located in Winner. 5 bedroom 1.5 bathroom. Fully stocked with anything & everything you may need for your stay. *Pets are allowed with $50 non-refundable fee. This will be added to your invoice. Pets are allowed in heated laundry room, or in the front porch, not in the main part of the house.

Picturesque Sunsets at our 7-bedroom Country Home

Experience some of the wold's best sunsets on our farm, just a few miles off of I-90. Hop on the interstate with quick access to the Corn Palace in Mitchell or Al's Oasis in Chamberlain. We're only 4 hours from Mount Rushmore, so it's a perfect stopping point to relax for a day (or several) before your final push to this beauty. If you're coming to experience the area's famous hunting, look no further. We're located right in the heart of pheasant country. We look forward to hosting you!

Carriage House - Private Dwelling. 3 beds, 1 bath

The Carriage House is a private, separate dwelling located on the property of Molly's Manor B&B. Unique and comfortable, 525 sq. ft. No step entry. Main floor includes a bedroom with one Queen-size bed, a cozy living room, fully equipped kitchen with appliances and cookware, and bathroom with a large shower; W/D. Two full-size beds in the upstairs loft, including a futon. Non-smoking, pet-free. Minisplit for AC/heat, Smart TV and WiFi. Plenty of parking for vehicles/boat.

The Rustic MP6

Relax with the whole family at this peaceful place to stay. two bedrooms one queen bed other full bed. the living room has two sofas with beds in them. they are full size and queen size beds. Just recently added a rollaway bed (twin size) can host up to 5-9 people if you don't mind sharing a bed. no smoking or no pets inside. beautiful view!

Grandma’s House - peaceful, 28 miles to Niobrara

Enjoy the peace and quiet of this quaint old farmhouse on a working farm/ranch in the country, 28 miles to Niobrara River in Nebraska, 26 miles to Sparks, for tubing and canoeing, 45 miles to Valentine, Nebraska, 28 miles from Winner, SD. Ask about a camper hookup, outdoor arena for riding, weather permitting, and pens for your horses.

The Hide-A-Way

Have fun in the heart of pheasant country on the east edge of Winner, South Dakota. This newly remodeled space has been converted from an old lumber yard into a homey and comfortable space. It's less than a mile from town and is conveniently located on Us Highway 18. Within walking distance to the drive-in theater and local museum.

Spacious Duplex Getaway

Bring the whole family to this great place with lots of room for fun. Great screened in porch for evening sitting, family games including a foosball table. Full kitchen, washer & dryer, smart tv, and fireplace. The Co-Host live on the other side. The duplex is located only 15 miles from the Missouri River.

Comfortable Cottage

Comfortable and cozy small home on large lot. lots of green space for kids and pets. Close to many small town attractions. 15 minutes away from the beautiful Missouri River. Water sports, fishing, hunting, and picnic/beach areas.

Platte Cottage

Adorable 2 bedroom housekeeping cottage. Fully equipped kitchen with fridge, range and mw. Great Location For fishing, hunting and other outdoor activities. Town has full services. Drive-through driveway for trailers. Cable TV.