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.

Tails Up Retreat | Premier Basecamp in Webster, SD

Tails Up Retreat – Your Glacial Lakes Basecamp Just blocks from downtown Webster, Tails Up Retreat is a cozy, pet-friendly home built for outdoor adventure and relaxed family stays. Enjoy a heated garage with TV, a heated fish & game cleaning shack, great outdoor living with grills and a firepit, plus family-friendly extras like a Pack ’n Play, high chair, and kids’ toys. With fast Wi-Fi, quiet mini-split A/C, in-unit laundry, and space for up to 8 guests, it’s the perfect place to unwind after

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.

Cozy 3 br Home - Fireplace & Heated Garage Spaces

Enjoy our 2-br, 2-ba home fully furnished for your stay! Scenic trails and a park are just steps away. Only a 5-minute drive to the Prairie Lakes Ice Arena and downtown Watertown. Enjoy a gas fireplace in a cozy 4 seasons room, a spacious kitchen, a "man cave" with a 75" TV, a relaxing master bedroom with a king-size adjustable bed, and a versatile office that can also serve as a bedroom, with an optional air mattress. Attached heated garage stalls included. Comfortably sleeps 6 guests.

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.

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.

Sportsman’s Country Lodge: The Fish House

Located in Webster, SD, this is a full service home with 2 bedrooms and 1 bathroom upstairs. There are 2 full beds, three twins (bunks), and a single bed in the bedrooms. There is also a queen bed in the pull-out couch in the living room. If you aren't fishing enjoy the 65 inch tv or the poker table. There is off street parking with a boat plug-in and a cleaning station in the garage. Please just take your fish scraps when you leave. TV is smart.

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.

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!

Heaven on the Prairie

A big house, the kind most American kids dreamed of growing up in. Settled on the furthest edge of town, this 7 bedroom, 3 bath house is private, yet convenient. The 100-mile view as the horses run up for the evening makes it hard to leave! Contact us for whole-house rates, and long-term discounts. NOTE: please put in the correct number of guests for an accurate price.