Vacation rentals in Castlewood

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Top-rated vacation rentals in Castlewood

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Guest favorite
A cozy cabin features a welcoming porch with two chairs positioned beside a small table. The cabin, painted in warm tones, is flanked by nearby cabins on a grassy area. The clear blue sky adds a bright backdrop to the inviting entrance.
Cabin in Watertown
4.98 out of 5 average rating, 40 reviews

Cabin #2-Harvest

It is beautifully furnished with a queen bed, comfortable recliners, a table & chairs, and includes a microwave, refrigerator, & coffee service. The luxurious bathroom features limitless hot water & a step-in shower. Our cabins are available year-round. We furnish bed linens/towels. We don't provide housekeeping unless the stay is one week or more.  At that time, we will clean the linens/towels and entire space and charge an additional $25.  Extended stays will follow this same weekly pattern.

Top guest favorite
Apartment in Watertown
5 out of 5 average rating, 52 reviews

Restful Retreat * 2nd floor apt

Lovely 2nd floor apartment, spotlessly clean and tastefully decorated! We're located right in the center of town, with private driveway parking and close to everything. Full kitchen with dishes, cookware, all appliances. Large bedroom has queen-sized bed, small bedroom has twin bed. Living room has three recliners, smart TV, high-speed wifi, and comfy nook with an additional twin mattress & toys for the kids. Private entrance. Patio and gas grill are shared with the owners and are yours to use!

Top guest favorite
The exterior of the cabin is showcased, featuring a well-maintained façade with a garage and large windows. The lawn is grassy and bordered by trees, while the driveway provides ample parking space. A glimpse of the lake is visible in the background.
Cabin in Watertown
4.93 out of 5 average rating, 243 reviews

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.

Top guest favorite
A cozy living area is highlighted by a modern electric fireplace beneath a wall-mounted television. A vibrant horse painting adds color to the space, while a plush sofa is complemented by a decorative yellow ottoman and greenery, creating a welcoming relaxed atmosphere.
Barn in Watertown
4.96 out of 5 average rating, 119 reviews

Silverstar Stables is perfect for long-term stays.

Silverstar Stables is located on 10 acres 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. Silverstar Barn 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.

Guest favorite
Home in Brookings
4.85 out of 5 average rating, 52 reviews

Cozy and Small near DT Brookings

This is a small space in a duplex home near downtown Brookings. It boasts a stand up washer and dryer, and a queen bed! The space is perfect for one person traveling, a couple or a couple of people coming to town to work. The second room has a twin in a very small space, should a second person want a bed or a third person possibly. Our hope is to offer an inexpensive location for people that are traveling to town, working temporarily in town, or need a quick stay on their way somewhere.

Top guest favorite
Lush green trees line the serene lake, reflected perfectly across the calm water's surface. The vibrant greenery and stillness create a peaceful natural setting, enhancing the tranquility of the nearby surroundings.
Guesthouse in Florence
5 out of 5 average rating, 30 reviews

Serenity Stay at GLHL

Nestled in the rolling hills of E. SD and a short walk to a gorgeous lake, our lodge features two cozy bedrooms and a loft with 1 queen and 6 double beds. Enjoy two bathrooms, complimentary coffee and cold breakfast items & WIFI. With direct lakeside access and expansive grounds for outdoor activities, Glacial Lakes Hunting Lodge and Guide Service is ideal for relaxation and adventure. This is a guest house on the property we live on with our animals- no free roaming pets.

Top guest favorite
Cabin in Watertown
4.97 out of 5 average rating, 64 reviews

South Lake Haven

South Lake Haven is a sportsman’s paradise and perfect for family getaways. Located across the street from Lake Kampeska, it features a top-tier game/fish cleaning station and lots of sportsman amenities along with ample trailer parking. After a day outdoors, unwind by the fire pit or enjoy the pool table, foosball, and board games. With 3 bedrooms, full kitchen, and luxury amenities, it’s ideal for hosting your hunting crew or making unforgettable family memories.

Top guest favorite
A modern lake home features a sleek black exterior, positioned near the water. A wooden pathway leads down to the rocky shoreline, framed by green landscaping. Large windows provide a view of the serene surroundings, enhancing the connection between indoor and outdoor spaces.
Cabin in Castlewood
4.96 out of 5 average rating, 26 reviews

New build lake poinsett cabin

Come check out Lake Poinsetts newest lake home rental. Only a few miles from the golf course, convenience stores, restaurants and nightlife. The house/cabin is brand new construction that provides large spacious views and lake access within feet of the back patio. It has a large pass through garage living space with bar. During summer months a dock is included for any of your recreational desires. We would love to host you!!

Superhost
A lake-front cabin features a welcoming exterior with large windows and a spacious lawn. A patio is visible with seating arrangements and a path leading to the water's edge. Trees provide shade, complementing the serene environment under a partly cloudy sky.
Home in Watertown
4.6 out of 5 average rating, 10 reviews

KampeskaCabin:Firepit,Hammock,Lakefront

🌊 Updated lakefront cabin perfect for family memories 🛏 Sleeps 4 Jan–Apr (King + bunk beds); upper level opens May–Aug 🔥 Enjoy sunsets, hammock time, and evenings by the fire pit 🏖 Easy lake access + space to unwind and recharge 📍 Located on South Lake Drive near campground for extra guests ❤️ Heart this listing to save it to your Guest Favorites! ***Effective Aug 28th, 2025 NO DOCK available until Spring 2026)***

Top guest favorite
A spacious living room is showcased, featuring a large sectional sofa in rich black leather. Natural wood paneling creates a warm ambiance, complemented by two standing lamps and framed artwork on the walls. Light enters from the window, illuminating the soft area rug beneath.
Cabin in Estelline
4.97 out of 5 average rating, 158 reviews

3-Bedroom House on Lake Poinsett

Escape to the lake! Come out and relax with family and friends! Year-round enjoyment - swimming, open water fishing, kayaking, ice fishing, snowmobiling and more! You will have private access to the lake with a dock. The dock is generally in the water May through Labor Day. Note: There are several stairs required to get down to the dock. Boat ramp and shared public beach nearby. Floating water mat available.

Top guest favorite
An exterior view of the retreat showcases a well-maintained, single-story building with a light brown facade. A welcoming sign featuring the word 'WELCOME' is visible beside a red bench adorned with flowers, while an American flag is displayed, creating a charming entrance.
Guest suite in Hayti
4.98 out of 5 average rating, 178 reviews

Salt and Light Retreat~ Overnight Stays - rural SD

Relax and get away from it all! A place to Literally UNPLUG from the world! A bit of a drive out, enjoying the farmlands you will find our Salt and Light Retreat for overnight stays. Private entry, garage parking, clean and comfy! Complimentary breakfast & full time coffee bar available We are not allowing pets at this time. Perhaps kenneled hunting dogs may work out Fishing trip? Boat parking available

Guest favorite
A cozy living area is present, featuring a spacious beige sofa with a decorative pillow, a comfortable armchair, and a wooden coffee table displaying magazines. A light-colored area rug covers the floor, while large windows allow natural light to fill the room.
Farm stay in Estelline
4.9 out of 5 average rating, 145 reviews

A Taste of Farm Living

A peaceful place in the country, yet only two miles from town. Twenty minutes from numerous lakes and many walk- in hunting areas. Not outdoorsy? Shopping and activities for the kids (Children's Museum, SDSU Ag Museum and Redlin Center) are close by in Watertown and Brookings. Or, hang out at the farm, watch the chickens peck in the grass, and roast marshmallows in fire pit.

Popular amenities for Castlewood vacation rentals

  1. Airbnb
  2. United States
  3. South Dakota
  4. Hamlin County
  5. Castlewood