Vacation rentals in Castlewood

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Top-rated vacation rentals in Castlewood

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Barn in Watertown
4.95 out of 5 average rating, 303 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, 239 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.

Superhost
A circular fire pit area is surrounded by six metal chairs, positioned on a grassy lawn. Lush greenery including trees and shrubs offers a natural backdrop, enhancing the outdoor space of the two-story cabin visible in the background.
Cabin in Gary
5 out of 5 average rating, 3 reviews

Brookside Cabin

Stay in a natural paradise in our Brookside two-story cabin. A special place with modern amenities; in one of the most scenic and beautiful woodlands in the Eastern Dakotas. A fully equipped kitchen, small dining area, and living room. With three comfortable bedrooms with two bathrooms. Private decks, perfect for sipping your morning coffee, just a few feet from Cobb Creek. In the evenings, gather at the fire pit for stargazing and s'mores! New to Airbnb, but a quest favorite for years!

Superhost
A modern kitchen is equipped with updated appliances, including a stainless steel refrigerator and a gas stove. Countertops are finished in a light marble design, complemented by a mosaic backsplash. Natural light filters in through a window, offering a view of the outdoor area.
Cabin in Watertown
4.91 out of 5 average rating, 11 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.

Superhost
Home in Brookings
4.82 out of 5 average rating, 45 reviews

Cozy and Small near DT Brookings

This is a small space in a duplex home near downtown Brookings. It boasts a stand up washer and dryer, and a queen bed! The space is perfect for one person traveling, a couple or a couple of people coming to town to work. The second room has a twin in a very small space, should a second person want a bed or a third person possibly. Our hope is to offer an inexpensive location for people that are traveling to town, working temporarily in town, or need a quick stay on their way somewhere.

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, 150 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, 186 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.

Top guest favorite
A grassy area is featured alongside the lake, with a wooden fence and a pathway leading to the water. String lights are hung overhead, providing ambient lighting. Two lounge chairs are positioned on the lawn, accented by orange pillows, inviting relaxation by the lakeside.
Guest suite in Watertown
4.98 out of 5 average rating, 139 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