Holiday houses in Day County

Modern Loft in Historic Building on Main Street

In the heart of what's happening in Webster: shopping, bars, fishing, hunting, and more. Centrally located on Main St. "The Loft" is an intimate vacation rental providing guests with a convenient, modern, and comfortable experience. Completely renovated in 2021 to be modern and cozy with all new furnishings. The layout has been thoughtfully designed to be flexible to the needs of our guests; cozy for a couple, yet flexible to accommodate up to 6. Space to park boat or shack with power hook-up.

Anglers Lodge

Unwind from a day of fishing or hunting at this Webster, SD home. 2 story house sleeps 15 people (6 queen & 3 twin) has 2 bathrooms, full kitchen and dining area. Attached, heated garage with bar area! Enjoy the scenery as the Webster golf course/basketball courts are across the street. Street parking with outdoor/indoor electrical hook ups for your boat. Dogs are welcome but not on the furniture, please. Webster is also kid friendly and offers a city park & swimming pool with water slides!

J & Z Sportsman's Getaway

Our home is conveniently located in Webster close to main street, walking distance from most of the restaurants and bars. Centrally located in the Glacial Lakes area, for great fishing & hunting. We provide a 2nd garage for cleaning & frying your fresh caught fish. Boat parking and electrical hook up is also available in garage. Dine outside on the patio with the BBQ grill. You will enjoy all the comforts of home, cozy new beds, living room furniture, and a kitchen with all the necessities.

Dewey’s Place is for Hunters/Fisherman/Families

Here's your perfect fishing/hunting destination, with space for all your buddies, big family, and/or dogs too! Located within 10 miles of 7+ lakes including Bitter Lake, Waubay Lake, and Enemy Swim and prime hatch area for waterfowl. Perfect for families visiting or groups of outdoorsman looking for a large space where everyone (or almost everyone) gets a bed! Cozy in the winter, cool in the summer, and homey all year round. Host is an area hunter and fisherman with guide experience.

Horseshoe Lodge

3 bedroom, 1.5 bath ranch style house with attached 3 car garage perfect for large family or group getaways! Home sleeps 11 people with 9 twins and 1 queen bed. Corner lot with lots of parking space on the street and driveway. Driveway has room for parking 3 boats off the street! Outside plugins for charging boat batteries. Living room has large TV with Youtube TV provided for your stay. Walking distance to downtown businesses! Pets are welcome but must stay in the garage.

Peace of Lake, Apartment suite, Pickerel Lake SD

Located at Pickerel Lake, one of the best clear-water lakes in northeast South Dakota, the apartment above our garage offers guests all-seasons year-round access for fishing, hunting, boating, and water recreation activities on Pickerel Lake and on other area lakes. From a keypadded shared entryway up 16 standard-incline steps to the apartment are two bedrooms, living room, full kitchen, full bath with shower, plus free parking outdoors including area for boat/trailer parking.

Top 5% Airbnb | No service fee | Tails Up Retreat

Locally owned & managed | Sleeps up to 7 guests Fenced backyard | Traeger grill, Blackstone grill, and Solo-stove Outdoor dining set and patio chairs for relaxation | Cornhole Smart TVs | Free high-speed internet. Memory foam mattresses for a comfortable night's sleep Well-stocked kitchen | Coffee bar Heated garage | Heated game and fish cleaning shack | Large driveway. Discover hospitality at its finest and make memories that will last a lifetime at Tails Up Retreat.

Glacial Lakes Retreat

Nestled in the serene Glacial Lakes region of South Dakota, our unique family-friendly cabin offers the perfect blend of rustic charm and modern comfort. This retreat is a haven for fishing and hunting enthusiasts. With cozy interiors it's an ideal escape for quality family time or outdoor adventures. The cabin is equipped with all the amenities needed for a comfortable stay, ensuring a memorable experience in the heart of nature. Minimum two night stay for booking.

Honey Hole Hideaway

Bring the whole family to this great place with lots of room for fun. This house sits on 3 town lots, so there is plenty of space to park and enjoy the outdoors. Fully furnished with 5 beds, 2 giant couches and 2 recliners. Full size washer/dryer, full kitchen, outdoor Weber gas grill. There is also a bar/grill just a short walk from the house. We welcome hunters and fishermen or anyone just looking for a clean comfortable place to stay.