Holiday rentals in Gregory

Modern home near Missouri River

Unwind and relax at this centrally-located home. Located on Platte’s beautiful Main Street only a few blocks from downtown shopping, grocery store, and gas stations. It is a 15 minute drive to the Missouri River: fishing, beaches, canoeing, swimming. This home has a single stall garage and plenty of driveway space for boats. The backyard has a concrete patio with table and chairs for relaxing after a long day at the river or on the road while you enjoy the view of Platte’s South Park pond.

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.

The Lodge

Located on the Edge of town in Gregory, South Dakota. pop 1250. A great place to stay when visiting the area or family. Large grassy yard, easy to find, clean and comfortable. We have an outdoor space with tables and a grill. Gregory County is in the Pheasant Triangle, Known for Big Whitetail, and is 35 mins from the Missouri River. Pets are allowed Outdoors in the kennel area. Please no pets indoors. Please send us a message if you have any questions or need help with a booking.

The Old Hayloft

Adventure awaits you in this rustic getaway. Just a short drive off of HWY 183 south of Colome to stay in this super cute old hayloft that had been renovated as guest quarters. Stair access externally. This is not handicap accessible and very rustic. It is on the second story. 2 bedroom 1 bath. Full bed in bedroom #1 and a set of twin beds in bedroom 2 and the third bedroom is an open loft (no door up steeper stairs) with another set of twin beds. Total guests is up to 6.

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.

Retro Chic Getaway

What do you get when the ’70s and ’90s have a love child? This apartment. Just off Main St in Winner, SD, this 2-bedroom throwback delivers bold vibes with all the essentials. It’s clean, affordable, and perched above a local tech company (tech troubles? Yep—we know a guy). You’ll be steps from restaurants, bars, and—shameless plug—one of the best tattoo shops in the Midwest. Step inside, soak up the patterns, and let nostalgia run wild. Welcome to your vintage getaway!

Twin Pine River House

Relax with the whole family at this peaceful river cabin. Located on the Missouri River hills near Platte Creek Recreation Area near Platte, SD. Enjoy all this area has to offer: fishing, boating, beaches, hiking, pheasant hunting, deer hunting, turkey hunting, ice fishing. Newly finished garage with air conditioning and heat, very pet friendly. Looking to relax, enjoy the beautiful sunrises on the front porch or sunsets on the back deck.

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 two rollaway beds (twin size) can host up to 5-10 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.

Cozy Corner

Clean small 2 bedroom house in a quiet neighborhood. It is a cozy place to relax in. Sit by the outdoor fire pit and grill out or enjoy the indoor fireplace. 10 minute drive to the river. We have a grocery store, restaurant, coffee shop, and bar.

Rustic Ridge

Have fun with the whole family at this stylish place. While enjoying the outdoors only 3 miles from Gregory .