Vacation rentals in Castlewood

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Top-rated vacation rentals in Castlewood

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Top guest favorite
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
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, 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.

Top guest favorite
A spacious deck overlooks a serene lake, with a round dining table and seating for six. A bar height table for four is positioned nearby. Soft clouds reflect the warm hues of the sunset across the water, enhancing the tranquil atmosphere.
Cabin in Estelline
4.91 out of 5 average rating, 44 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
4.92 out of 5 average rating, 12 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 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, 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!!

Guest favorite
An aerial view captures the vineyard home surrounded by rows of grapevines, with protective nets covering the crops. The spacious property features a combination of open fields and wooded areas. The house showcases multiple levels, with large windows overlooking the scenic landscape.
Home in Volga
4.91 out of 5 average rating, 113 reviews

4 bedroom vineyard home near Brookings, SD

Enjoy a get-away in a vineyard home. Beautifully decorated inside and out! Walk through the grape vines, sample the grapes, taste the wine and relax! The spacious 4 bedroom home has plenty of room for large groups. Open concept and multiple levels allow for your guests to come together and enjoy meals and conversation. A huge 800 sq ft patio makes for amazing outdoor entertaining. Enjoy the sunset over the vines.

Top guest favorite
A tranquil view of an inviting swimming pool reflects the evening sky, with lush green fields extending into the distance. The surrounding area features a well-kept lawn and trees, creating a peaceful outdoor atmosphere.
Guest suite in Hayti
4.98 out of 5 average rating, 172 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, 187 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.

Top 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, 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 spacious hot tub occupies the foreground, with water glistening under soft light. A fire pit is visible in the distance, surrounded by gravel, and a wooden fence outlines the backyard, where trees and seating areas provide a peaceful setting.
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.

Guest favorite
An inviting open-concept living space showcases modern furnishings and large windows offering scenic lake views. A private deck with outdoor seating is featured, complemented by a lillypad on the lake, while paddleboards are nearby for recreational activities.
Home in Arlington
5 out of 5 average rating, 7 reviews

Hunting,Fishn,FamFriendly,Sleeps16,LakesideLux

✨ Modern Lakefront Getaway – Sleeps 16 🌅 Stunning sunsets on quiet Lake Albert 🏡 4BR • 3BA • 3 living spaces • Full kitchen 🎮 Games, Lilly Pad, 2 paddle boards & pickleball 🔥 Deck, grills, private dock & fire table ❤️ Tap the heart to save this stay to your Guest Favorites!

Popular amenities for Castlewood vacation rentals

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