Holiday rentals in Webster

5 out of 5 average rating, 23 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.

4.95 out of 5 average rating, 272 reviews

Barn in Watertown

Silverstar Barn

Silverstar Barn is located on 10 acres just 3 miles south of Watertown on blacktop road. It is approximately 150 feet from our residence. Rest assure that you will be left alone to enjoy your extended or weekend getaway. We have just completed remodeling the other half of the barn turning it onto another rental. Silver star Stables has it's own entrance and both units have there own patio doors, one facing east, the other west for private outdoor seating. Both units have there own grill as well.

4.92 out of 5 average rating, 226 reviews

Cabin in Watertown

Lakefront Cozy Cabin - Watertown Kampeska

This lakefront cabin is freshly remodeled in 2013, and includes all the amenities! Warm colors, dog friendly, plenty of parking, great for a summer getaway with the crew, or a winter getaway with the family. Room to beach or anchor a boat, and if the lake is frozen, perfect location to wake right up and head out on the ice to fish. Kayaks available for use! Bedrooms sleep 2 people each, and there is a loveseat and couch in the living room. Two cots also available to sleep additional people.

4.91 out of 5 average rating, 11 reviews

Anglers Lodge 3

Come and enjoy what Webster has to offer with this 3 bed, 2 bath ranch house that sleeps 8. Has attached 4 stall heated AND air conditioned garage that will fit a 22’ boat, utv’s and other fishing/hunting equipment. Garage has tv, dart board and foosball table to play after a long day of fishing/hunting! Huge lot for parking in the back and alley access. Pets welcomed, just not on furniture. Webster is also kid friendly and offers city park, basketball courts and city pool with waterslides!

5 out of 5 average rating, 9 reviews

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.

4.93 out of 5 average rating, 29 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, 162 reviews

Home in Waubay

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.

4.93 out of 5 average rating, 30 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.

4.95 out of 5 average rating, 115 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.

5 out of 5 average rating, 37 reviews

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.

5 out of 5 average rating, 26 reviews

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.

4.95 out of 5 average rating, 20 reviews

Home in Bradley

Springer's 1886 Lodge

The 1886 Lodge located in Bradley SD in the heart of the Glacial Lakes region. Which has excellent fishing, hunting, & outdoor recreation opportunities. Our lodge was originally the first Bradley school. It has open concept which can sleep up to 7 guests with a queen bed, 3 singles, & a sofa sleeper. Other amenities include a full bath, half bath, full kitchen, & laundry. Hunting dogs are welcome!

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Other great holiday rentals in Webster

4.68 out of 5 average rating, 76 reviews

Sportsman's Country Lodge: The Duck House

BrandonRating, 5 stars1 month ago

Place was great! Garage isn’t quite big enough to get a 19’ boat in all the way.

Home in Waubay

4.8 out of 5 average rating, 157 reviews

The Lodge at the Lake

ScottRating, 5 stars2 days ago

Worked out great. Would definitely stay again.

4.68 out of 5 average rating, 19 reviews

Pets welcome 2BR | Grill, Fire Pit, Boat Parking

ShaneRating, 5 stars24 months ago

Great place to stay for fishing in the area. The place was accurately described and had all the amenities we required. Rebecca was great communication and very accommodating.

5 out of 5 average rating, 7 reviews

Home in Henry

M & M Hideaways

ShaneRating, 5 stars1 week ago

We had an amazing stay at the M & M Hideaway. The place exceeded our expectations in every way and Melissa was an amazing host. The house was like brand new and had every amenity you could need provided. It's in close proximity to some of our favorite lakes to fish in SD. We look forward to staying here in the future.

Home in Waubay

4.74 out of 5 average rating, 68 reviews

The Fish Crib Lodge- The Perch

LengRating, 5 stars1 week ago

Host was very responsive and quick; that's a huge plus for me. Everything was functional (i.e. hot water, appliances, heat and A/C, etc.). The ice machine and washer/dryer are also huge pluses. Shane offers a guided fishing service which I'm curious about for the next trip.

Flat in Roslyn

4.73 out of 5 average rating, 11 reviews

Northside Lodging- Unit 4: Single Efficiency Room

ShaneRating, 5 stars1 week ago

Always clean and quiet place to stay. Shannon is super responsive and flexible for outdoorsmen who are coming and going at all hours of the day.

5 out of 5 average rating, 8 reviews

Cabin in Waubay

Family Cabin on Enemy Swim

NancyRating, 5 stars3 days ago

We had a wonderful stay! The cabin is clean & modern with all the essentials you need for your stay. We really enjoyed that the cabin is right on the north side of Enemy Swim Lake. We caught several fish right off the dock. Katie was also quick to respond to our questions.