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Castlewood Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Castlewood vacation rentals

A hot tub on a wooden deck with a view of the water.

1. Private Sauna, Hot Tub, Beach – Lake Poinsett

Private Sauna, Hot Tub, Beach – Lake Poinsett
Lake Norden
9.4 out of 10, Exceptional, (67 reviews)
"Nice place"
United States
Anonymous traveler
$320 nightly
The price is $337
Sep 28 - Sep 29
Total with taxes and fees
Private Sauna, Hot Tub, Beach – Lake Poinsett
A hot tub on a wooden deck with a view of the water.

2. Private Sauna, Hot Tub, Beach Lake Poinsett

Private Sauna, Hot Tub, Beach Lake Poinsett
3.0 star property
Lake Norden
$334 nightly
The price is $353
Sep 28 - Sep 29
Total with taxes and fees
Private Sauna, Hot Tub, Beach Lake Poinsett
A two-story house with a deck and a staircase leading to the entrance.

3. Cozy beach front lake cabin with hot tub!

Cozy beach front lake cabin with hot tub!
Lake norden
8.0 out of 10, Very good, (16 reviews)
"It was great, big enough for our family of six to be comfortable."
United States
Jessie C.
$394 nightly
The price is $415
Sep 27 - Sep 28
Total with taxes and fees
Cozy beach front lake cabin with hot tub!
A house with a porch, a staircase leading to the entrance, and various potted plants.

4. 2-bedroom Sleeping Rooms in fantastic Watertown SD with WiFi, AC

2-bedroom Sleeping Rooms in fantastic Watertown SD with WiFi, AC
Watertown
9.4 out of 10, Exceptional, (6 reviews)
"Perfect spot for a quick overnight stay!"
United States
Tracy S.
$150 nightly
The price is $161
Oct 1 - Oct 2
Total with taxes and fees
2-bedroom Sleeping Rooms in fantastic Watertown SD with WiFi, AC
A living room with a TV, wooden door, and a small table with a chair.

5. Cozy 1-bedroom apartment in delightful Arlington

Cozy 1-bedroom apartment in delightful Arlington
Arlington
10.0 out of 10, Exceptional, (4 reviews)
"Perfact for our short stay...close to main street."
United States
Wanda H.
$126 nightly
The price is $135
Sep 27 - Sep 28
Total with taxes and fees
Cozy 1-bedroom apartment in delightful Arlington
A modern outdoor patio with a fire pit, a covered seating area, and a wooden fence.

6. Modern farmhouse oasis. - horses welcome

Modern farmhouse oasis. - horses welcome
Watertown
10.0 out of 10, Exceptional, (31 reviews)
"Enjoyed our quick get away here. Easy to get to and great communication with host."
United States
Joni L.
$393 nightly
The price is $414
Sep 27 - Sep 28
Total with taxes and fees
Modern farmhouse oasis. - horses welcome
A dock extending into a body of water with a house in the background.

7. New Deck|Fishing|Lakeside|FamFriendly|RVHookup

New Deck|Fishing|Lakeside|FamFriendly|RVHookup
Watertown
10.0 out of 10, Exceptional, (10 reviews)
"Perfect for what we needed! Kids had a blast fishing off the dock!"
United States
Tiffany B.
$579 nightly
The price is $618
Sep 29 - Sep 30
Total with taxes and fees
New Deck|Fishing|Lakeside|FamFriendly|RVHookup
An outdoor patio with stone flooring, metal chairs, and benches, surrounded by trees and a grassy field.

8. 5 BR/2.5 BA Hunting & Fishing Lodge

5 BR/2.5 BA Hunting & Fishing Lodge
Watertown
10.0 out of 10, Exceptional, (78 reviews)
"This a great place to stay. Very clean, roomy, and well set up for a big group!"
United States
Cody P.
$590 nightly
The price is $621
Sep 27 - Sep 28
Total with taxes and fees
5 BR/2.5 BA Hunting & Fishing Lodge
A spacious living room with a large flat-screen TV, multiple seating options including a recliner and two sofas, and a wooden entertainment center.

9. Perfect 4-bedroom building. Perfect for your next hunting or fishing adventure.

Perfect 4-bedroom building. Perfect for your next hunting or fishing adventure.
Bryant
9.0 out of 10, Wonderful, (2 reviews)
"Eugene was an incredible host. We had a group of seven, plus five dogs, and there was more than enough space to spread out, including all our gear. Having the dogs free to roam made it feel even more like home. The huge stainless sink for cleaning birds indoors was a total game changer and honestly amazing. We had a fantastic time and will definitely be booking again next year."
United States
Nicholas
$295 nightly
The price is $316
Sep 30 - Oct 1
Total with taxes and fees
Perfect 4-bedroom building. Perfect for your next hunting or fishing adventure.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Castlewood Hotel Reviews

Holiday Inn Express & Suites Watertown by IHG

Holiday Inn Express & Suites Watertown by IHG

10/10 Excellent
"Very nice place to stay."
VINCENT 1-night trip
Posted 19 hours ago
Holiday Inn Express & Suites Watertown by IHG

Find out more about Castlewood

Everything you need to know about Castlewood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Castlewood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castlewood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castlewood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castlewood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Castlewood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $161 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Castlewood rentals

At Expedia, we put the best Castlewood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Castlewood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castlewood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castlewood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Castlewood?

Yes, we offer vacation rentals near top attractions in Castlewood, or you can go with a secluded option if you're looking for relaxation.

What are some of the best vacation home rentals that Castlewood has to offer?

Lake Poinsett Waterfront Property: This highly rated vacation home rental in Castlewood is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games. Another good choice for your trip to Castlewood is Lakefront Retreat w/ Fire Pit & Dock in Castlewood.

How many vacation rentals are there in Castlewood?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Castlewood stay.

What can I see and do in Castlewood?

Explore the area and family-friendly sights such as Bramble Park Zoo, or get out into nature at a spot like Lake Poinsett. In the larger area, you’ll find Terry Redlin Museum and Watertown Mall.

What are vacation rentals like in Castlewood?

Vacation rentals are privately owned accommodations you can reserve for a couple days or more in Castlewood. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.