Vacation rentals in Castlewood

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Top-rated vacation rentals in Castlewood

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Top guest favorite
The exterior of a cozy cabin features an orange facade with a wooden sign reading 'Lighthouse.' A welcoming porch is seen, furnished with two dark wicker chairs. Large windows and a brown front door complete the inviting entrance, framed by a railing.
Cabin in Watertown
5 out of 5 average rating, 28 reviews

Cabin #4-Lighthouse

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.

Guest favorite
A living area is presented with a modern gray sofa positioned near a small black coffee table. Light pours in through a set of windows, highlighting the wooden flooring and exposed ceiling beams. A television is mounted on the opposite wall, complementing the minimalist decor.
Apartment in Watertown
4.95 out of 5 average rating, 38 reviews

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.

Top guest favorite
A private outdoor patio features gray stone pavers, surrounded by red mulch and small green plants. Two chairs are positioned near a fire pit, with a grill located nearby. Sliding glass doors provide access to the barn's interior.
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, 28 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
The exterior of the single-story home showcases a warm beige facade with a combination of stone accents. It features a landscaped front yard with ornamental grasses and rocks. The attached heated garage is visible, with two garage doors providing access for parking.
Home in Watertown
5 out of 5 average rating, 12 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 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, 109 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 deck overlooking the lake features a circular fire pit surrounded by four chairs. A wooden walkway leads to the water's edge, while the serene lake surface reflects the sky. Lush greenery is present along the edge of the deck.
Cabin in Estelline
4.97 out of 5 average rating, 143 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).

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, 168 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
The exterior of a single-story house features a light-colored facade with a welcoming front porch. A small garage with a star decoration is visible to the right. Lush green grass surrounds the property, complemented by trees in the background.
Home in Brookings
4.91 out of 5 average rating, 179 reviews

Brookings Haven

This home will be all yours when you book! There are three beds, two bathrooms and two different living room areas with TVs to unwind after a long day of sports or work. This house is located near the Hillcrest Aquatic Center so you will be pretty well centrally located. The property has a large patio with a charcoal and gas grill available for guest use and two different kitchen areas.

Guest favorite
A single-story home with pale yellow siding is surrounded by lush green grass. A wooden deck with steps leads to the entrance, providing a space for outdoor seating. Trees and a partially visible barn are in the background, enhancing the rural setting.
Farm stay in Estelline
4.89 out of 5 average rating, 135 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.

Top guest favorite
A cozy living area features a large sectional sofa adorned with soft pillows, facing expansive windows that offer a view of the lake. A wooden coffee table is positioned in front, and a decorative wall piece adds a touch of character to the room.
Guest suite in Watertown
4.98 out of 5 average rating, 132 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
4.85 out of 5 average rating, 84 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!

Popular amenities for Castlewood vacation rentals

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