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, 283 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.

Guest favorite

A serene lakefront view features calm waters reflecting the clear sky. A wooden dock extends into the lake, with several covered boats secured to the sides. Shadows from nearby trees softly fall on the concrete pathway leading to the water.

Cabin in Watertown

4.93 out of 5 average rating, 232 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

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, 31 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

An open living space is observed, featuring a cozy seating area with a sofa and large wall-mounted television. A round wooden dining table with four chairs is positioned next to a well-equipped kitchen. Natural light filters through two windows, highlighting the rustic decor.

Guest suite in Astoria

5 out of 5 average rating, 52 reviews

Sokota Suite in the Country

Our suite is located on our peaceful farm.We are just a 10 minute drive to 2 lakes, Lake Cochrane, and Lake Hendricks and a 2 minute drive to Fish Lake. We have 5 different golf courses within a 20 minute drive and they are all open to the public ! We are located 30 miles, an easy country drive, to Brookings/SDSU.Our farm is on a paved highway and you can enjoy a quiet walk to a beautiful country church just 1/8 mile away. We have an unattached garage that you can have access to use for a fee,

Guest favorite

A contemporary single-story home is highlighted, featuring a warm beige facade and a well-maintained front yard. The driveway accommodates several vehicles, leading to a double garage. Soft grass, landscaped stones, and a small decorative bush enhance the welcoming entrance.

Home in Watertown

5 out of 5 average rating, 8 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 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, 128 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 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

4.93 out of 5 average rating, 76 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 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, 164 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

A light-filled living area is furnished with two sofas, a large wooden coffee table, and a sleek entertainment unit. A flat-screen TV is mounted on the wall, and decorative art pieces hang nearby. Soft texture rugs cover the floor, contributing to a cozy atmosphere.

Home in De Smet

5 out of 5 average rating, 18 reviews

The 605 House

The little 605 house on the prairie! Nestled just on the edge of town this little 1 bed 1 bath makes for the perfect place to stay. Inside you’ll find a full kitchen, sofa bed for extra guests, washer and dryer, and stylish bathroom. Enjoy the prairie views while on the deck complete with a picnic table, grill, and patio chairs. Enjoy your stay at The 605 House!

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

4.98 out of 5 average rating, 122 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 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

An inviting loft space features a spacious bedroom with a plush bed covered in soft linens. A kitchenette with modern appliances is visible on the left, while a bathroom door leads to a well-lit, elegantly designed area. A Smart TV is mounted on the wall, and natural light enhances the warm color scheme.

Apartment in Brookings

4.94 out of 5 average rating, 100 reviews

Evergreen at 418

Nestled in the heart of vibrant Downtown Brookings, this freshly remodeled loft apartment offers a perfect blend of cozy comfort and elegant style. With its prime location, you'll have everything you need right at your doorstep, from charming boutiques to delectable dining options.