Holiday rentals in Roslyn

5 out of 5 average rating, 30 reviews

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.

Superhost

Home in Roslyn

4.83 out of 5 average rating, 41 reviews

Roslyn Creamery Co. - Hunting/Fishing Getaway

Charming spacious brick building, once Roslyn Creamery Co., now the perfect weekend getaway! Centrally located, close to all the best fishing and hunting spots in NE South Dakota. Comfortably sleeps up to 12 people. Features: Indoor & outdoor hot tubs. Wood burning stove. Smart T.V.s in the living room and two bedrooms. Modern amenities. Commercial flat-top stove w/two ovens. Valley Cougar 8 dart board. Vintage Ms. Pac-Man machine. Pets allowed! Enclosed outdoor space for pets w/dog door.

4.94 out of 5 average rating, 34 reviews

SD Country Living at its Best!

GORGEOUS HOME WITH 5 BEDROOMS, 2 LIVING ROOMS, FULL KITCHEN, 3.5 BATHROOMS, 2 LEVELS, 4,000 SQ FEET, LAUNDRY ROOM, 250 sq FEET DECK, WORKOUT EQUIPMENT, TANNING BED, GRILL, 8 TV's, GRANITE COUNTER TOPS, WiFi , POOL TABLE, FULLY FURNISHED, LOCATED ON 10 ACRES OF LAND! CONVENIENT AND BEAUTIFUL LOCATION NW OF WEBSTER, SD. CLOSE TO MANY GLACIAL LAKES. 3 MILES FROM LYNN LAKE, 7 MILES FROM WAUBAY LAKE, MAKE YOURSELF AT HOME IN OUR RURAL HOME! GAME CLEANING AVAILABLE IN WEBSTER AT THE GALLEY.

4.95 out of 5 average rating, 165 reviews

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.

4.91 out of 5 average rating, 33 reviews

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.

4.81 out of 5 average rating, 166 reviews

The Lodge at the Lake

The Lodge at the Lake is a half-mile from both Bitter Lake and Blue Dog Lake and a few short miles from Enemy Swim, Pickeral, Waubay, and Rush lakes. We are also close to great hunting areas. We have plenty of room for your entire party. Our house features a large TV, wifi, foosball table, 2 stall garage to park out of the elements, outdoor seating and fire bowl, a large grill, and the yard is big to give you some privacy. We have 3 bedrooms and room for at least 10 people to sleep.

4.95 out of 5 average rating, 125 reviews

Guest suite in Grenville

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.

4.94 out of 5 average rating, 18 reviews

Cabin in Waubay

Oak & Arrow Cabin

This waterfront home is a true stunner and ready to help you and your family relax and make memories. A complete renovation in 2019 transformed this home into a gorgeous retreat ready for families, hunters, anglers, and anyone else looking for a great getaway on the water. The home features gorgeous views of Bluedog Lake and modern furnishings. It has three bedrooms and three full bathrooms and comfortable sleeps 8 adults. You won't find a more peaceful property in the area!

Superhost

4.69 out of 5 average rating, 58 reviews

Blue Dog Escape

As of November of 2025, our Airbnb will be temporarily unavailable due to remodeling. We are excited to have it updated! Our adorable 1,467 square feet lake home is a perfect place to relax and unwind. Just a short walk from the Purple Cow (Ice cream and food) and Dollar General. A little further south there is a gas station to get groceries, hardware and tackle. HUNTERS & FISHERMAN WELCOME! Absolutely no loud parties.

4.91 out of 5 average rating, 66 reviews

Waubay Walleyes & Wings Retreat

Located on the north end of Waubay Lake in NE South Dakota - in the heart of great walleye fishing & pheasant hunting. A great place to simply enjoy some time away! The 3 bedrooms, plus loft area with 5 beds, and 3 bathrooms provide ample space for up to 13 people. Enjoy the pool table in the family room and the lake views from the 38' deck. Outdoor space is plentiful with ample parking and a firepit!

4.85 out of 5 average rating, 175 reviews

Home in Lake City

Come relax on the lake!

Enjoy your summer at the lake. THIS THE LOWER LEVEL OF A HOUSE ON ROY LAKE. It is separate from the upstairs and has its own entrance on the lake. Includes access to dock and close to boat dock. (Our dock is only in the water from May-Sept) 2 bedrooms (1 King bed, 2 queen beds), and large sectional couch. Has kitchenette, private bathroom, gas grill, fire pit. Bring your boat!