Pet-friendly holiday rentals in Webster

4.88 out of 5 average rating, 17 reviews

Hideaway on Main- No cleaning fee-Local Owned

The Hideaway on Main is large enough to sleep up to 12. Features a large pull thru driveway, as well as large yard, perfect for trailers and boats without having to park on the street! A heated and cooled cleaning shack for game and fish is provided. Pets are allowed in the house but NOT on beds or other furniture. The Webster area offers many hunting and fishing opportunities. Home is located on main street, walking distance to excellent restaurants and bars and grocery store just blocks away.

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.

4.95 out of 5 average rating, 281 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.

4.93 out of 5 average rating, 231 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.

5 out of 5 average rating, 31 reviews

Flat in Watertown

Cozy & Close

Small but quaint, you will definately get that COZY feel the minute you walk in! You will have all of the comforts of home, but with a BONUS!! When you venture out, you will be CLOSE by, within walking distance to the best or Watertown's eateries, 2 breweries, Gather Coffee Shoppe! Entertainment all year long, at the infamous Goss Opera House, in warmer months enjoy being right across the street from Watertown's Foundation Park, home to outdoor music and entertainment, and main street events.

4.88 out of 5 average rating, 42 reviews

Anglers Lodge

Unwind from a day of fishing or hunting at this Webster, SD home. 2 story house sleeps 15 people (6 queen & 3 twin) has 2 bathrooms, full kitchen and dining area. Attached, heated garage with bar area! Enjoy the scenery as the Webster golf course/basketball courts are across the street. Street parking with outdoor/indoor electrical hook ups for your boat. Dogs are welcome but not on the furniture, please. Webster is also kid friendly and offers a city park & swimming pool with water slides!

4.95 out of 5 average rating, 165 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.

4.91 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

Home in Waubay

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.

4.94 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!

5 out of 5 average rating, 39 reviews

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.