Castlewood Holiday Rentals

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Holiday Rentals in Castlewood

Lake Front Fun, Pheasant Hunting, & Ice Fishing
9.6 out of 10, Exceptional, (40)
"The property was just want we needed for our first SD pheasant hunting weekend of 2023. All the amenities we needed. Clean and excellent location. The only thing that could have made it any better would be the addition of a hot tub on the wonderful back deck over looking the lake. Thanks for letting us stay."
Lake Front Fun, Pheasant Hunting, & Ice Fishing
Lakefront Vacation Rental with Fire Pit & Dock!
9.8 out of 10, Exceptional, (6)
"This property was in a friendly neighborhood. The house was very well set up and decorated. Handy supplies and dishes as well. Would definitely go back."
Lakefront Vacation Rental with Fire Pit & Dock!
Waterfront Lake Poinsett Retreat: Boat Dock, Slip!
10.0 out of 10, Exceptional, (2)
"Beautiful location for a family retreat with all the extras included! Grill, outdoor cooler, patio umbrella, firepit. The interior of the cottage is just as nice. The decks space is amazing offering great views of the lake. The best feature is the sun room! super comfy sofas and chairs for enjoying coffee in mornings and taking in the sunsets on the lake regardless of weather! Wonderful! Host is super responsive!"
Waterfront Lake Poinsett Retreat: Boat Dock, Slip!
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Sunrise & Sunsets Lake Poinsett.2 bedroom 2 bath
10.0 out of 10, Exceptional, (7)
"Great stay."
Sunrise & Sunsets Lake Poinsett.2 bedroom 2 bath
Lake Poinsett Cottage at Stone Bridge
Lake Poinsett Cottage at Stone Bridge
Cozy 3 bedroom Beach Front Home
9.8 out of 10, Exceptional, (16)
"cabin was great, just what we needed for the weekend of fishing with my son in law's. the wheather was not the greatest and the fish were not bitting but we still had a great time. would rent the cabin again some time. thanks for renting it to us. bob p."
Cozy 3 bedroom Beach Front Home
Lakefront Lake Poinsett Cottage with Private Beach
Lakefront Lake Poinsett Cottage with Private Beach
Lakefront Vacation Rental With Fire Pit & Dock!
3.5 star property
Lakefront Vacation Rental With Fire Pit & Dock!
Waterfront Lake Poinsett Retreat: Boat Dock, Slip!
3.0 star property
Waterfront Lake Poinsett Retreat: Boat Dock, Slip!
Cozy house on north shore of Lake Poinsett
Cozy house on north shore of Lake Poinsett
Watertown Condo w/ Resort-Style Amenities!
10.0 out of 10, Exceptional, (8)
"Great place"
Watertown Condo w/ Resort-Style Amenities!
Private lake front property with huge patio!
9.8 out of 10, Exceptional, (85)
"Very quiet place to get away. Bed was comfortable."
Private lake front property with huge patio!
Chic & Cozy Cabin with Private Hot Tub & Beach!
9.2 out of 10, Wonderful, (29)
"Very clean and well maintained property."
Chic & Cozy Cabin with Private Hot Tub & Beach!
Updated Cabin with Hot Tub: Walk to Boat Ramp!
9.2 out of 10, Wonderful, (19)
"We like the fact that we could use the hot tub and the dock where we catch most of our fish. The atmosphere and neighbors are really friendly."
Updated Cabin with Hot Tub: Walk to Boat Ramp!
Modern Home on Lake Poinsett! 3 bed + Loft on the beach!!
10.0 out of 10, Exceptional, (19)
"Lovely property"
Modern Home on Lake Poinsett! 3 bed + Loft on the beach!!
Waterfront Watertown Condo w/ Patio & Pool Access!
10.0 out of 10, Exceptional, (6)
"Although the weather wasn't amazing, the views of the lake were. Would definitely stay again."
Waterfront Watertown Condo w/ Patio & Pool Access!
5 BR/2.5 BA Hunting & Fishing Lodge
10.0 out of 10, Exceptional, (59)
"Very quiet house, plenty of room for larger group. Plenty of kitchen supplies and 2 refrigerators. Easy to find and access town."
The price is NZ$1,030
per night
3 Jun - 4 Jun
5 BR/2.5 BA Hunting & Fishing Lodge
Penthouse on Kampeska in Watertown
Penthouse on Kampeska in Watertown
House on back lot Lake Poinsett New Construction
The price is NZ$731
per night
3 Jun - 4 Jun
House on back lot Lake Poinsett New Construction
#3 Bohemian Rest Place
4.8 out of 10, (3)
"My car blew up so I didn’t get to stay and there was no refund option"
The price is NZ$118
per night
5 Jun - 6 Jun
#3 Bohemian Rest Place
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See all available properties in Castlewood
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.

Other types of properties in Castlewood you may be interested in

Lakefront Vacation Rental with Fire Pit & Dock!
9.8 out of 10, Exceptional, (6)
"This property was in a friendly neighborhood. The house was very well set up and decorated. Handy supplies and dishes as well. Would definitely go back."
Lakefront Vacation Rental with Fire Pit & Dock!
Waterfront Lake Poinsett Retreat: Boat Dock, Slip!
10.0 out of 10, Exceptional, (2)
"Beautiful location for a family retreat with all the extras included! Grill, outdoor cooler, patio umbrella, firepit. The interior of the cottage is just as nice. The decks space is amazing offering great views of the lake. The best feature is the sun room! super comfy sofas and chairs for enjoying coffee in mornings and taking in the sunsets on the lake regardless of weather! Wonderful! Host is super responsive!"
Waterfront Lake Poinsett Retreat: Boat Dock, Slip!
Lake Front Fun, Pheasant Hunting, & Ice Fishing
9.6 out of 10, Exceptional, (40)
"The property was just want we needed for our first SD pheasant hunting weekend of 2023. All the amenities we needed. Clean and excellent location. The only thing that could have made it any better would be the addition of a hot tub on the wonderful back deck over looking the lake. Thanks for letting us stay."
Lake Front Fun, Pheasant Hunting, & Ice Fishing
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Castlewood holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Castlewood. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Castlewood. Seeing all the best attractions is bound to make you fall in love with Castlewood. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Castlewood short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Castlewood?

Yes, there are holiday rentals close to the most popular sights in Castlewood, or you can select a more secluded option if you're looking for a relaxing stay.

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

Lake Front Fun, Pheasant Hunting, & Ice Fishing : This highly rated holiday home rental in Castlewood is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Other favourite homes for rent in Castlewood are Lakefront Vacation Rental with Fire Pit & Dock! and Waterfront Lake Poinsett Retreat: Boat Dock, Slip!.

How many holiday rentals are there in Castlewood?

With 7 Expedia holiday rentals, you're guaranteed 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 Watertown Family Aquatic Center, or get out into nature at a spot like Lake Poinsett. In the wider area, you’ll find Terry Redlin Museum and Watertown Mall.

What are holiday rentals like in Castlewood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Castlewood. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a family getaway.

Recent reviews of Castlewood properties
Expedia verified reviews