Holiday rentals in Roslyn

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.

Uptown in a Small Town ~ Cozy 3BD + Garage

Whether family, business, or recreation brings you to Britton, enjoy your time at our well-equipped, conveniently located home! Located just ONE BLOCK from the Britton Event Center and close to the pool, this home is a convenient and classy launch point for your stay. We are avid AirBNB’ers and look forward to making your stay the best possible! Home highlights: great location, newly remodeled, attached garage, enclosed backyard, pack-n-play, a fully equipped kitchen, and an open floorplan.

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.

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.

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.

Sportsman's Country Lodge: The Duck House

Located in Webster, SD and the heart of the Glacial Lakes region, The Duck House by Sportsman's Country Lodge provides an ideal location and quick access to a hunter's and fisherman's paradise. This location offers 3 bedrooms and 1 bathroom and can comfortably sleep up to 8 guests. We offer a large driveway for off the street parking, designated fish and game cleaning area (please take scraps with you), outdoor outlet for boat charging, WiFi, and we are working on a game room.

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.

Ginger House - Cozy 2 bedroom

Escape to picturesque Roy Lake. Perfect getaway for all seasons. Perfect for guests seeking a tranquil getaway. Enjoy the many activities and sites of NE South Dakota. Many amenities are included full kitchen, laundry, family room, WIFI, TV and air conditioning. Whether you're exploring the stunning surroundings or simply unwinding in the inviting atmosphere, this terrific property offers a delightful escape. Fall in love with Roy Lake and enjoy the magic it has to offer.

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.

Roslyn Creamery Co. - Hunting/Fishing Getaway

Charming, spacious brick building—once the Roslyn Creamery Co.—now a comfortable base for lake days and field time in NE South Dakota. Right on Main Street, steps from a local bar & grill, with contactless check-in and plenty of parking. Sleeps up to 12 on a single level with an easy, open layout. After a long day, soak in the indoor & outdoor hot tubs, light the wood-burning stove, and unwind with classic games.

Gone Fishing & You Should Too!Stay @TailsUpRetreat

Relax, recharge, and reel in the good times at Tails Up Retreat! This pet-friendly getaway in the Glacial Lakes Region is ideal for families and outdoor enthusiasts alike. Enjoy a heated garage, fish/game cleaning station, cozy living spaces, and a fenced yard for your pup — all just blocks from downtown Webster. Discover hospitality at its finest and make memories that will last a lifetime at Tails Up Retreat.

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!