Vacation rentals in Roslyn

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Top-rated vacation rentals in Roslyn

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Top guest favorite

A spacious living area is present, featuring a large, dark sectional sofa arranged around a pair of circular tables. Natural light fills the space through multiple windows, with a textured area rug lying beneath. A cozy accent chair adds a pop of color to the room.

Home in Webster

5 out of 5 average rating, 31 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

A welcoming common area features comfortable seating with black leather couches and dark wooden chairs. A large flat-screen TV is mounted on the wall, and a dart board is visible in the corner. Warm light from overhead fixtures illuminates the space, highlighting the rustic decor.

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.

Top guest favorite

The entryway features a wooden deck with a seat set, inviting relaxation. A welcome sign adorns the wall, complemented by decorative pumpkins. Smooth gravel surrounds the area, while a large rock enhances the natural landscape. Expansive windows provide views of the surrounding scenery.

Home in Webster

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.

Top guest favorite

The exterior of the house is depicted, featuring a pitched roof with shingles, a welcoming front door, and a wooden deck with railing. Windows allow natural light to enter, and a well-maintained lawn surrounds the home. A driveway is visible on the side.

Home in Waubay

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.

Guest favorite

A mounted fish is displayed against a neutral wall, with realistic detailing showing scales and fins. It appears to be a bass, with a lure positioned near its mouth. The fish is surrounded by a decorative arrangement of rocks and greenery, enhancing the presentation.

Home in Webster

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.

Guest favorite

The exterior of a two-story house features a welcoming front porch with wooden railings. A large double garage with two doors is visible alongside the house, while a well-maintained lawn with green grass and ornamental shrubs surrounds the property under a clear blue sky.

Home in Waubay

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.

Top guest favorite

A wooden dock extends into a calm, reflective lake, surrounded by trees on the horizon. The scene captures a tranquil blue twilight sky, creating a serene atmosphere. Soft ripples across the water's surface reflect faint lights from distant shores.

Guest suite in Grenville

4.95 out of 5 average rating, 125 reviews

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.

Guest favorite

The cabin is positioned by the water, featuring a wooden dock extending into the lake. A seating area with white chairs is located on the grassy shore, surrounded by smooth rocks. Large windows line the front of the home, reflecting the serene outdoor setting.

Cabin in Waubay

4.94 out of 5 average rating, 18 reviews

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!

Top guest favorite

A welcoming corner is displayed with a rustic barn painting hanging above a welcome sign. Decorative wall-mounted jars filled with flowers are positioned on either side. A vintage-style clock stands on the counter, complementing the friendly atmosphere of the space.

Home in Clark

5 out of 5 average rating, 52 reviews

The Windmill House

The Windmill House is located in Clark, SD. The kitchen is fully furnished, towels and bedding provided, washer and dryer available if needed. Sleeping arrangements include a king, twin, full, and hide-a-bed. Extra amenities include WiFi, Roku TV, games, outdoor grill, and a shed set up for fish/game cleaning. Clark has one of the largest public pools in the state, a 9 hole golf course, several excellent dining options, and some of the best fishing and hunting in SD.

Superhost

An open kitchen space is highlighted by wood cabinets and a countertop. Key appliances, including a refrigerator and stove, are visible. A small dining table is positioned in the corner. Light-colored flooring enhances the room's spacious feel, with a ceiling fan providing airflow.

Home in Pierpont

5 out of 5 average rating, 3 reviews

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.

Superhost

A serene view of Blue Dog Lake is captured at sunset, displaying vibrant hues of pink, orange, and purple reflecting on the water's surface. A wooden dock extends into the lake, framed by lush trees and rocky shorelines.

Home in Waubay

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.

Guest favorite

A wooden dock extends over the smooth surface of the lake, offering direct access to the water. The surrounding view includes calm waters reflecting a clear sky and distant tree lines along the shoreline.

Home in Lake City

4.85 out of 5 average rating, 176 reviews

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!