Vacation rentals in Castlewood

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Top-rated vacation rentals in Castlewood

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Top guest favorite

A red barn structure is depicted with a distinctive peaked roof and large windows. Two vehicles are parked in front, and a windmill stands nearby against a clear blue sky. The area is surrounded by green grass and hints of the natural landscape beyond.

Farm stay in Hayti

5 out of 5 average rating, 25 reviews

Rustic Retreat

Relax at this unique & tranquil barn loft. The main loft features a large living area w/ additional sleeping options, TV & swing. The kitchen & bath are also on this level. An additional half loft holds 2 bedrooms. We’re secluded on 160@ of conservation habitat in the heart of prairie pothole region. There are many public hunting/fishing areas nearby. We offer places to clean your game/fish as well as a fire pit & seating to enjoy the prairie sunset. Dogs welcome w/ notice. RV hookup available.

Top guest favorite

An open living space is observed, featuring a cozy seating area with a sofa and large wall-mounted television. A round wooden dining table with four chairs is positioned next to a well-equipped kitchen. Natural light filters through two windows, highlighting the rustic decor.

Guest suite in Astoria

5 out of 5 average rating, 54 reviews

Sokota Suite in the Country

Our suite is located on our peaceful farm.We are just a 10 minute drive to 2 lakes, Lake Cochrane, and Lake Hendricks and a 2 minute drive to Fish Lake. We have 5 different golf courses within a 20 minute drive and they are all open to the public ! We are located 30 miles, an easy country drive, to Brookings/SDSU.Our farm is on a paved highway and you can enjoy a quiet walk to a beautiful country church just 1/8 mile away. We have an unattached garage that you can have access to use for a fee,

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, 115 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

A cozy living space is presented with a blue sofa and an upholstered floral chair. Two small ottomans sit in front, complemented by a patterned area rug. Light filters through the windows, enhancing the simplicity of the decor.

Home in Brookings

4.86 out of 5 average rating, 21 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.

Guest favorite

A contemporary single-story home is highlighted, featuring a warm beige facade and a well-maintained front yard. The driveway accommodates several vehicles, leading to a double garage. Soft grass, landscaped stones, and a small decorative bush enhance the welcoming entrance.

Home in Watertown

5 out of 5 average rating, 10 reviews

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.

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, 136 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. Inquire about floating water mat if interested (additional cost).

Guest favorite

A wooden deck, surrounded by trees, features a six-person hot tub overlooking the lake. Soft lighting casts a warm glow as the serene water reflects the evening sky, with a private dock visible in the background.

Home in Estelline

4.94 out of 5 average rating, 87 reviews

Charming Lake House, Hot Tub, Sauna, Private Dock

Welcome to Your Perfect Lakeside Retreat! Nestled on the serene shores of Lake Poinsett, SD, this charming lake house offers the ultimate getaway for families and couples alike. With 3 cozy bedrooms and 1 modern bathroom, you'll find everything you need for a relaxing and memorable stay. Enjoy breathtaking lake views from the private dock, unwind in the hot tub, or warm up in the sauna after a day of outdoor adventure.

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, 167 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

Top guest favorite

A light-filled living area is furnished with two sofas, a large wooden coffee table, and a sleek entertainment unit. A flat-screen TV is mounted on the wall, and decorative art pieces hang nearby. Soft texture rugs cover the floor, contributing to a cozy atmosphere.

Home in De Smet

5 out of 5 average rating, 29 reviews

The 605 House

The little 605 house on the prairie! Nestled just on the edge of town this little 1 bed 1 bath makes for the perfect place to stay. Inside you’ll find a full kitchen, sofa bed for extra guests, washer and dryer, and stylish bathroom. Enjoy the prairie views while on the deck complete with a picnic table, grill, and patio chairs. Enjoy your stay at The 605 House!

Top guest favorite

A lakefront patio area is visible, featuring two lounge chairs with orange cushions, set on green grass. A fire pit is positioned nearby, and a dining table with chairs is located under strings of lights next to large glass doors leading into the interior.

Guest suite in Watertown

4.98 out of 5 average rating, 128 reviews

Kampeska Lakefront Cottage

You will have access to one side of this lakefront duplex located directly on the lake. This property has two bedrooms, one bathroom, a washer and dryer as well as a fully furnished kitchen. This is the perfect getaway to enjoy the beautiful Lake Kampeska. Bonus: Enjoy a massage in your very own massage chair located in one of the bedrooms.

Guest favorite

A charming single-story house is depicted, featuring a sloped roof and a covered front porch. The pale exterior is complemented by a large window, and a landscaped garden adds greenery to the yard. A concrete pathway leads to the entrance.

Home in Estelline

4.84 out of 5 average rating, 79 reviews

Sportsman Cabin

Relax with the whole family at this cozy place to stay. This is also a sportsman friendly house with a detached 2 stall garage. Cleaning station in the garage if needed and located just minutes from Lake Poinsett! We also have guide services available for fishing, pheasant, deer and waterfowl!

Guest favorite

An inviting loft space features a spacious bedroom with a plush bed covered in soft linens. A kitchenette with modern appliances is visible on the left, while a bathroom door leads to a well-lit, elegantly designed area. A Smart TV is mounted on the wall, and natural light enhances the warm color scheme.

Apartment in Brookings

4.93 out of 5 average rating, 113 reviews

Evergreen at 418

Nestled in the heart of vibrant Downtown Brookings, this freshly remodeled loft apartment offers a perfect blend of cozy comfort and elegant style. With its prime location, you'll have everything you need right at your doorstep, from charming boutiques to delectable dining options.