Vacation rentals in Castlewood

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Top-rated vacation rentals in Castlewood

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Top guest favorite

A modern kitchen is presented with stainless steel appliances and an expansive granite countertop. Bright red metal stools are positioned at the counter, complementing the rustic wood paneling and unique decor elements. Natural light filters through a window, illuminating the open space.

Barn in Watertown

4.95 out of 5 average rating, 279 reviews

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.

Top guest favorite

The kitchen features wooden cabinetry, stainless steel appliances, and a large island with a granite countertop. Natural light fills the space, accentuating the warm tones of the wooden floors. Two chairs are positioned at the island, providing an inviting spot for casual dining.

Home in Watertown

5 out of 5 average rating, 54 reviews

Luxury Lake Home on 2 acr.+ Rent Pontoon/jet-ski

Exclusive Lake Luxury home This stunning 4-bedr, 2.5-bath home is designed for large families. The gourmet kitchen is stocked for memorable meals. Enjoy 200' of sandy beach on the Pelican Lake. Unwind with gorgeous sunsets, or relax in the hot tub (approximate mid Apr–Oct), private dock, grill, & fire pit. Rent a Pontoon & jet ski from us. The fully remodeled interior features a movie room, office, coffee bar, mudroom, and 2-stall garage. A luxurious sanctuary for relaxation and adventure awaits

Top guest favorite

A newly renovated cabin is framed by tall trees and lush green grass, showcasing a vibrant red roof. The exterior features large windows and double doors that provide a welcoming entrance. The landscape reflects a tranquil setting in a peaceful neighborhood.

Vacation home in Lake Preston

4.97 out of 5 average rating, 104 reviews

Peaceful and quiet small town cabin

Come and enjoy our freshly renovated cabin located in the peaceful little town of Lake Preston, SD. We are located right in the heart of pheasant country! Our cabin is a wonderful base for your fishing outings. Lake Whitewood - 3 miles away; Lake Thompson - 4 miles; L. Poinsett - 20 miles; L. Henry- 21 miles; Dry Lake #2 - 27 miles. We have plenty of room for your boat/camper. Laura Ingall's Wilder's home is 9 miles away. Enjoy a very peaceful spot with the amenities of a small town.

Top guest favorite

A charming, single-story home is showcased with a well-maintained front yard featuring a green lawn and landscaped flower beds. A pathway leads to the entrance, and an American flag is displayed. A driveway is visible, along with a single-car garage.

Home in Watertown

5 out of 5 average rating, 28 reviews

Mayfair Drive

Welcome to our cozy, recently updated two-bedroom, one-bath home located in a quiet, safe neighborhood. Just minutes away from Prairie Lakes Hospital, this space is perfect for professionals, patients, or visitors seeking a peaceful retreat. Enjoy modern amenities, a fully equipped kitchen, two queen sized beds, and comfortable living spaces. Whether you're here for a short stay or an extended visit, you'll appreciate the convenience and serenity our home offers.

Top guest favorite

A modern kitchenette is featured with a concrete bar countertop and four high-backed stools. Industrial-style pendant lights hang above, providing warm illumination. The flooring is designed with wooden planks, adding a natural element to the space.

Apartment in De Smet

4.96 out of 5 average rating, 27 reviews

Ingalls Flat

Where modern meets historic charm. This newly renovated office space offers a unique stay in the heart of the little town on the prairie! Ingalls Flat is the perfect place to stay for travelers looking to explore the historic prairie town, business traveler, solo vacationers, couples looking for a private stay with many amenities, and anyone planning the perfect staycation! Located within walking distance of Calumet Ave, DeSmet’s historic “Main Street.”

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, 122 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 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

4.94 out of 5 average rating, 17 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!!

Guest favorite

A serene lakeside view features a wooden deck attached to the house, surrounded by trees. Two stand-up paddle boards rest beside a pathway, with kayaks in red and green lined along the shore. A gentle slope leads towards the tranquil water of Lake Poinsett.

Home in Estelline

4.94 out of 5 average rating, 66 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 airy living space features high ceilings and modern furnishings, including a gray sofa and wooden chairs. The kitchen is visible with an island and bar seating. Large windows allow natural light to fill the room, enhancing the open feel.

Cabin in Arlington

5 out of 5 average rating, 13 reviews

New Construction Modern Cabin on Lake Albert

New modern cabin on Lake Albert! Enjoy lakefront access and take in stunning views from our spacious patios. With 3 bedrooms, 8 beds our cabin is ideal for families and small groups. Conveniently located close to a beautiful golf course and Lake Pointsett public access boat docks. Watch the sunset and unwind in this serene getaway. Book your stay today and experience the perfect blend of comfort, nature and beauty.

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

4.97 out of 5 average rating, 158 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

Superhost

The modern kitchen features stainless steel appliances and granite countertops. A sleek coffee maker is on the counter, accompanied by glassware and dishware. Task lighting illuminates the space, while a framed cityscape artwork decorates the wall, enhancing the contemporary design.

Apartment in Watertown

4.75 out of 5 average rating, 16 reviews

Harry’s Mini-Suite

Enjoy a stylish experience at this centrally-located apartment. You’ll find with all the modern consciences, stainless appliances, granite counter tops, this newly renovated 1-bedroom is located above Harry’s Haircuts & Hot Towels, and the Hideaway Bar. Walkable to all other Downtown entertainment and events, and shopping.

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

4.83 out of 5 average rating, 72 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!