Vacation rentals in Castlewood

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Top-rated vacation rentals in Castlewood

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Top guest favorite
Apartment in Watertown
5 out of 5 average rating, 53 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!

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, 247 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 collage showcases the inviting features of the retreat. The top left displays a game area with a bar, emphasizing social space. The top right features the hot tub, ideal for relaxation. The bottom left highlights a rustic bedroom, and the bottom right displays a bunk bed setup, offering versatile sleeping arrangements.
Cabin in Estelline
4.92 out of 5 average rating, 50 reviews

Hottub|Bar+GameArea|Kayak|Paddleboards|Sleeps12+

🏡 Lake Poinsett Retreat – Spacious Lakefront Getaway! Welcome to Lake Poinsett Retreat, the perfect escape for families and groups looking for a relaxing and adventure-filled getaway. This 4-bedroom, 2-bathroom lakefront home comfortably sleeps up to 12 guests and offers breathtaking lake views, a private hot tub, and direct lake access. Whether you're here to fish, swim, kayak, or simply unwind, this home has everything you need for a memorable stay! Great for ice fishing, wood burning stove!

Guest favorite
A small green cabin is surrounded by tall trees, with a wooden deck featuring two chairs positioned at the front. A white door serves as the main entrance, and a gravel area leads to the cabin, providing a natural setting.
Cabin in Watertown
4.95 out of 5 average rating, 20 reviews

Cabin #5-The Cottage

Tranquil getaway with home comforts including furnished kitchen w/appliances, Farm style seating for 4, reclining loveseat, queen bed, beautiful bathroom. Cute front porch, side patio w/table for six, portable firepit. Surrounded by trees/privacy fence. Available year-round. Queen bed, linens/towels. Housekeeping not provided unless the stay is more than one week.  At that time, we will clean the linens/towels & entire space & charge an additional $25.  Same weekly pattern for extended stays.

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, 120 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
This open-concept living space features wooden ceilings and large windows that offer a view of the lake. A comfortable seating area includes dark leather chairs and a coffee table. Adjacent, a dining area with a table and several chairs is visible, creating an inviting environment.
Home in Arlington
4.97 out of 5 average rating, 58 reviews

Waterfront home on Lake Albert with a hot tub!

Relax with the whole family at this beautiful lakefront home. Perfect for fisherman, hunters, golfers or families visiting the Lake Poinsett, SD area. Enjoy a private beach steps away, dock, kayaks, Lily Pad, and close access to public boat landings and bars/restaurants. Located directly across from Lake Region Golf Course on the shores on Lake Albert, this home away from home will provide a peaceful stay with amazing sunsets and many local activities to enjoy!

Guest favorite
Home in Watertown
4.94 out of 5 average rating, 16 reviews

Lynwood Dr. Lake House

Relax with the whole family at Lynwood Lake House, a peaceful lakeside retreat on the west shore of beautiful Lake Kampeska in Watertown, SD. Enjoy stunning lake views and unforgettable sunrises. This thoughtfully remodeled home offers casual elegance with modern furnishings and high-end linens. Perfect for family getaways, it’s also an ideal hunting and fishing retreat, with excellent fishing on the lake and prime hunting nearby.

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, 27 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!!

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
4.98 out of 5 average rating, 164 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, 184 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, 147 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 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
4.97 out of 5 average rating, 145 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.

Popular amenities for Castlewood vacation rentals