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, 304 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
Cabin in Watertown
4.93 out of 5 average rating, 240 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.

Guest favorite
Cabin in Lake Benton
5 out of 5 average rating, 16 reviews

The Ridge

A cute cabin getaway in the heart of lake Benton, Minnesota located right beneath “Hole In The Mountain” state park. There is access to horse tails near by and walking distance from the cozy gem of a town. The lake is directly in front of the cabin and has public access right down the road. This is the perfect budget friendly get away for a family or a great place to lodge for hunting and fishing. Great in the summer and the winter! Snowmobile trails are also accessible nearby! 311 center st. N

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
4.92 out of 5 average rating, 13 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
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, 29 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.

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
4.92 out of 5 average rating, 51 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, 152 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
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, 24 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
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, 173 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
Farm stay in Estelline
4.89 out of 5 average rating, 140 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.

Guest favorite
A modern open floor plan is showcased, featuring a kitchen with dark cabinetry and stainless steel appliances. Comfortable seating arrangements are present, including a gray sofa and two armchairs. A dining table with white chairs sits nearby, illuminated by recessed lighting.
Farm stay in Watertown
4.96 out of 5 average rating, 81 reviews

Modern farmhouse oasis - horses welcome

Peaceful farmhouse getaway. Modern interior all high end appliances. Home gym with Peloton tread and bike, water rower, free weights. 2 car garage. Horse barn with indoor riding arena, stall up to 6 horses, turnout/pasture, pets welcome (see house rules), Backyard with hot tub, 3 fire pits, gazebo with furniture and screens, garden, grill. Kayaks.

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, 140 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

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