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, 272 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 charming cabin exterior is depicted, featuring a light gray facade with multiple windows that provide a view of the surroundings. A wooden porch extends out from the front, accompanied by a small fire pit on the stone pathway, enhancing the inviting outdoor space.

Cabin in Watertown

4.92 out of 5 average rating, 226 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 rustic bathroom features two pedestal sinks with classic faucets, each below a mirror. Illuminated by overhead lights, the space includes wooden walls and a toilet in the corner. A window offers natural light, and floor mats add comfort to the tile floor.

Farm stay in Hayti

5 out of 5 average rating, 23 reviews

Rustic Retreat

Relax at this unique & tranquil barn loft. The main loft features a large living area w/ additional sleeping options, TV & swing. The kitchen & bath are also on this level. An additional half loft holds 2 bedrooms. We’re secluded on 160@ of conservation habitat in the heart of prairie pothole region. There are many public hunting/fishing areas nearby. We offer places to clean your game/fish as well as a fire pit & seating to enjoy the prairie sunset. Dogs welcome w/ notice. RV hookup available.

Top guest favorite

A well-organized kitchen area features wooden cabinetry with multiple storage options. A white stove with an attached hood is positioned under a microwave. Counter space is available for meal prep, accented by a decorative kettle. Soft lighting enhances the welcoming ambience of the space.

Apartment in Watertown

5 out of 5 average rating, 15 reviews

Restful Retreat * 2nd floor apt

Lovely 2nd floor apartment, spotlessly clean and tastefully decorated! We're located right in the center of town, with private driveway parking and close to everything. Full kitchen with dishes, cookware, all appliances. Large bedroom has queen-sized bed, small bedroom has twin bed; twin air mattress available. Living room has three recliners, smart TV, high-speed wifi, and comfy nook with toys for the kids. Private entrance. Patio and gas grill are shared with the owners and are yours to use!

Guest favorite

A compact workspace is situated under the staircase, featuring a wooden desk and an ergonomic black office chair. A small basket and a speaker are placed on the desk, while light-colored walls create a bright, inviting atmosphere.

Home in Watertown

4.92 out of 5 average rating, 12 reviews

Cozy 2-Bed, 2-Bath Home

Located in a quiet neighborhood near Lake Area College, this split-level duplex unit features 2 bedrooms, 2 bathrooms, and an additional room in the basement. Each bedroom can sleep two; there is a sofa bed in the bonus room and a couch in the living room to sleep additional people. Each bedroom has a queen bed and closet space. The dining room includes a dinner table, which is expandable. If booked for over 7 days, we offer a 15% discount. If booked for over 28 days, we offer a 35% discount.

Top guest favorite

A spacious farmhouse is set amidst lush greenery, featuring a welcoming front porch adorned with lights. The structure's modern roof and white railings provide a charming view. A pathway leads to the entrance, while the expansive lawn offers a tranquil outdoor setting.

Guest suite in Astoria

5 out of 5 average rating, 50 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

The exterior of the single-story home showcases a warm beige facade with a combination of stone accents. It features a landscaped front yard with ornamental grasses and rocks. The attached heated garage is visible, with two garage doors providing access for parking.

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 fire pit is situated on a wooden deck, surrounded by seating. Flames dance among the fire stones, while a serene lake view is visible through the screened enclosure. Lush greenery is faintly seen in the background, adding to the tranquil setting.

Cabin in Estelline

4.97 out of 5 average rating, 116 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 circular fire pit constructed from metal features a lively fire burning brightly, with flames and glowing embers visible among the wood logs. The surrounding area is dark, enhancing the warm light emitted from the fire.

Cabin in Estelline

4.91 out of 5 average rating, 131 reviews

Malomar on beautiful Lake Poinsett!

Enjoy lakeside living on beautiful Lake Poinsett, SD. Spacious kitchen/great room with wood fireplace that opens to 12x24 foot patio-balcony with propane grill, table & chairs, and spectacular view of the lake. Sleeping for 10 makes it the perfect place for the whole family and fishing/hunting groups! Minutes from boat ramp, dining, groceries, golf & Lake Poinsett State Recreation Area. Keyless entry makes check-in a snap!

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

4.98 out of 5 average rating, 51 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

A red barn stands brightly against a partly cloudy sky, with a flag waving gently on a pole. Surrounding the barn, green grass and a garden of plants, flowers, and stones contribute to the outdoor landscape, while white fencing is visible in the background.

Guest suite in Hayti

4.97 out of 5 average rating, 154 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 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

4.97 out of 5 average rating, 113 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.

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Popular amenities for Castlewood vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Castlewood

Guest favorite

A tranquil lake scene is captured, featuring three white pelicans gliding across the calm water. A wooden dock extends from the shore, providing a direct view of the water, while smooth rocks border the lake's edge under a clear blue sky.

Cabin in Castlewood

4.85 out of 5 average rating, 33 reviews

Lakation Lake Poinsett Dock! 2 bed & bath

EmilyRating, 5 stars12 months ago

We had a great time! It is a beautiful property! They had all the essentials in the house, which we really appreciated. She was quick to respond to anything we needed. We had so fun making fires and playing in the water. We also loved that we could bring our pup with us. 10/10 🎉🙂

Cabin in Lake Norden

4.51 out of 5 average rating, 90 reviews

Chic & Cozy Cabin with Private Hot Tub & Beach!

AlexanderRating, 5 stars1 month ago

We had an excellent stay at this chic and cozy home on the lake. The views and morning sunrises were incredible and host was responsive and helpful. Looking forward to visiting again sometime.

Top guest favorite

The bathroom features a modern sink area with a wide mirror and stylish light fixtures. A shelf holds neatly rolled towels and toiletries. The area is designed for convenience with a washer and dryer visible in the background, alongside sleek cabinetry and contemporary decor.

Home in Henry

5 out of 5 average rating, 8 reviews

M & M Hideaways

ShaneRating, 5 stars2 weeks ago

We had an amazing stay at the M & M Hideaway. The place exceeded our expectations in every way and Melissa was an amazing host. The house was like brand new and had every amenity you could need provided. It's in close proximity to some of our favorite lakes to fish in SD. We look forward to staying here in the future.

A spacious patio area is visible, featuring several outdoor tables and chairs under vibrant red and black umbrellas. The lake stretches out in the background, framed by clear blue skies and distant greenery.

Cabin in Clark

5 out of 5 average rating, 4 reviews

Lodge on Indian Springs Lake

CamerynRating, 5 stars1 week ago

Beautiful property, very private and peaceful. Easy check in & check out, Casey was very responsive and helpful.

Guest favorite

A shaded outdoor space is shown, featuring an entrance door and a large grill positioned on a concrete surface. Sunlight filters through the trees, creating gentle shadows on the ground.

Home in Watertown

4.9 out of 5 average rating, 10 reviews

Dad’s Place

LystonRating, 5 stars1 week ago

Very nice size house, furiture was comfortable and clean. Bed room had plenty of room with night stands or a chair or maybe a dresser to put things on. Bathroom was short on towels, I'm sure if we asked Bill he would of got some more for us. Kitchen had the little things you somtimes need salt pepper,cooking oil ziplock bags ect. Bathroom the same shampo,body wash ect. Would use again for sure, so clean, felt homey.

Top guest favorite

A spacious living area features a dark, cushioned sofa positioned near large windows, providing views of the natural surroundings. The modern kitchen area includes a stainless steel refrigerator, enhancing the contemporary design. Soft lighting accents the dark cabinetry.

Camper/RV in Bradley

5 out of 5 average rating, 6 reviews

Indian Springs Glamping

BenRating, 5 stars7 months ago

Great place for us to stay for a long weekend of hunting. Comfortable for the 3 of us with everything we needed. Thanks!

Guest favorite

A rustic dining area is showcased, featuring a wooden table complemented by two matching chairs. A wooden bench is placed nearby, and a decorative farm-themed mural is positioned above a wooden backdrop, enhancing the country aesthetic.

Farm stay in Estelline

4.88 out of 5 average rating, 116 reviews

A Taste of Farm Living

JoshRating, 5 stars1 month ago

Kristy, you rock and we’re awesome to talk to and do business with. We appreciate your family’s hospitality and willingness to have us as guests. We definitely are going to hit you up next time we are working in town!

Guest favorite