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

A modern kitchen features a spacious island with eight stools, complemented by sleek cabinetry and stainless steel appliances. Hanging light fixtures provide illumination, and a comfortable seating area is visible in the background, enhancing the open layout.

Cabin in Arlington

4.97 out of 5 average rating, 32 reviews

Cabin on Lake Albert with hot tub & screened porch

This is the perfect home to enjoy beautiful Lake Albert and the Lake Poinsett Area! This modern home is ideal for your family vacation, golf trip, couple's getaway, hunting trip or fishing trip. Features large patio windows overlooking the lake, a beautiful 8-seat kitchen island, and a screened in patio with a 6-seat dining table. During the summer, take your kayak out on the lake or get a game of golf in. During the winter, enjoy ice fishing, hot tubbing, or stay cozy inside by the fireplace!

Guest favorite

A living area features a dark sofa paired with a low coffee table, complemented by a wall-mounted television. Hardwood floors are visible, and a ceiling fan is suspended above. A doorway leads to a bedroom, and natural light enters through a large window.

Apartment in Watertown

5 out of 5 average rating, 28 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 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, 29 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, 28 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, 123 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 wooden bench is positioned beside a decorative barrel featuring flower arrangements. A large 'WELCOME' sign is displayed next to the entrance door. Two windows reflect the warm light of the evening sun, enhancing the inviting atmosphere of the entryway.

Home in Clark

5 out of 5 average rating, 16 reviews

Lakehouse for hunters, fishermen & families!

Quiet, peaceful & serene country home on Indian Springs Lake 5 miles southeast of Clark, SD. Attention hunters & fishermen ... we now have heated garage for hunting dogs, vehicles and/or boats! **NEW PHOTOS COMING FALL 2025** Enjoy your stay in comfort with a beautiful lakeside view out the east and the best sunsets in the west. You can see and hear the wildlife run freely around the countryside and the fish in the lake are plentiful!

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!!

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, 14 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, 159 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 well-maintained exterior showcases a single-story home surrounded by a manicured lawn. Lush green grass is contrasted by flower beds and shrubs. A wooden deck is visible, and an American flag is displayed. Trees provide shaded areas around the property, contributing to the inviting atmosphere.

Home in Watertown

4.93 out of 5 average rating, 15 reviews

Dad’s Place

Your family will be close to everything when you stay at this centrally-located place. Excellent location for hunters and if you’re towing a boat, there is a drive through shop available for safe storage. (there is a fee of $25 per night to access the shop) Also internet and WiFi have just been added.

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!