Castleton Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Castleton holiday rentals

A deck with blue lounge chairs and a small blue boat, overlooking a river with a forested hillside in the background.

1. Tapioca Village Retreat

Tapioca Village Retreat
3.0 star property
Castleton
6.0 out of 10, (2 reviews)
"There is so much nature and friendliness! "
United States
Günter
The price is AU$114
includes taxes & fees
24 Nov - 25 Nov
Tapioca Village Retreat
A hotel room with a bed, a window with curtains, a desk with a computer, and a chair.

2. Abacus Jamaica the Zana Suite

Abacus Jamaica the Zana Suite
3.0 star property
Constant Spring
7.8 out of 10, Good, (75 reviews)
"Great spot for a quiet stay, staff was extremely helpful."
United States
Hopeton
The price is AU$155
includes taxes & fees
14 Nov - 15 Nov
Abacus Jamaica the Zana Suite
A modern hotel room with a large bed, a dark headboard, a small round table, a brown sofa, and a view of greenery through the window.

3. The Gardens

The Gardens
3.0 star property
Barbican
8.0 out of 10, Very good, (72 reviews)
"Nice an quite an joyful stay"
Canada
Damian Mark anthony
The price is AU$148
includes taxes & fees
15 Nov - 16 Nov
The Gardens
A wooden deck with a table and chairs, surrounded by lush greenery and a view of distant mountains.

4. Reggae Legends Estate

Reggae Legends Estate
3.5 star property
Jack's Hill
9.8 out of 10, Exceptional, (6 reviews)
"A really amazing find! Stunning location with fantastic views. Quiet and relaxing. The cabin was a great experience and we were so well looked after by Anne-Marie."
United Kingdom
Nicola
The price is AU$238
includes taxes & fees
18 Nov - 19 Nov
Reggae Legends Estate
A wooden bed with intricate carvings, a bedside lamp, and a robe hanging on the wall.

5. Windbreak Villa

Windbreak Villa
3.5 star property
Buff Bay
10.0 out of 10, Exceptional, (1 review)
The price is AU$158
includes taxes & fees
25 Nov - 26 Nov
Windbreak Villa
A two-story building with a swimming pool in the foreground.

6. Wave Crest Resort Race Course

Wave Crest Resort Race Course
2.5 star property
Oracabessa
10.0 out of 10, Exceptional, (1 review)
"The host came out to greet us. Very warm welcome. Large rooms. Clean. Friendly and very helpful staff. Would definitely stay here again !!"
United States
Beverly
The price is AU$212
includes taxes & fees
20 Nov - 21 Nov
Wave Crest Resort Race Course
A modern living room with a sofa, coffee table, and television.

7. Urban Charm: Modern One Bedroom

Urban Charm: Modern One Bedroom
New Kingston
9.6 out of 10, Exceptional, (18 reviews)
"Everything looked exactly like the pictures and communication was quick from the host. Would have no problem staying again."
United States
Alvin
The price is AU$217
includes taxes & fees
14 Nov - 15 Nov
Urban Charm: Modern One Bedroom
A bedroom with a bed, a window with curtains, a door, and a refrigerator.

8. Cozy studio apartment with queen bed in charming Kingston with AC

Cozy studio apartment with queen bed in charming Kingston with AC
Constant Spring
10.0 out of 10, Exceptional, (1 review)
"They are missing the AMAZING VIEW Tthat comes when u get inside the place"
United States
Mika
The price is AU$113
includes taxes & fees
14 Nov - 15 Nov
Cozy studio apartment with queen bed in charming Kingston with AC
A coastal property with a house surrounded by trees, a beach, and rocky terrain.

9. Magical Romantic Getaway For 2, Lovers Paradise On Private White Sand Beach Cove

Magical Romantic Getaway For 2, Lovers Paradise On Private White Sand Beach Cove
St Mary
The price is AU$392
includes taxes & fees
20 Nov - 21 Nov
Magical Romantic Getaway For 2, Lovers Paradise On Private White Sand Beach Cove
A kitchen with a granite countertop, stainless steel faucet, and a coffee machine.

10. Modern 1BR Condo in Kingston

Modern 1BR Condo in Kingston
2.0 star property
Half Way Tree
10.0 out of 10, Exceptional, (1 review)
"Excellent location absolutely loved it. The only thing was they had ants… everywhere"
United States
Robin
The price is AU$366
includes taxes & fees
14 Nov - 15 Nov
Modern 1BR Condo in Kingston
A modern kitchen with a central island, stainless steel appliances, and bar stools.

11. 1BR Comfort City Apartment with pool

1BR Comfort City Apartment with pool
2.0 star property
Kingston
10.0 out of 10, Exceptional, (1 review)
"Good"
United Kingdom
Shavel
The price is AU$424
includes taxes & fees
24 Nov - 25 Nov
1BR Comfort City Apartment with pool
A nighttime view of a swimming pool with a cityscape in the background.

12. City Apartment in Kingston AC with Pool

City Apartment in Kingston AC with Pool
3.0 star property
Half Way Tree
The price is AU$342
includes taxes & fees
21 Nov - 22 Nov
City Apartment in Kingston AC with Pool
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a sink. There are two black bar stools and a marble floor.

13. The Cozy Curve: Full 2 Br 2 Bth Apartment in Central location in Kingston

The Cozy Curve: Full 2 Br 2 Bth Apartment in Central location in Kingston
Havendale
8.8 out of 10, Excellent, (3 reviews)
"Was kinda worried at first when I was unable to find the location but Jamodi was very helpful in assisting with all information needed. The place was also clean and nice"
United States
Kimberly
The Cozy Curve: Full 2 Br 2 Bth Apartment in Central location in Kingston
Eazy Breezy

14. Hassle Free Getaway Beach Front Property, family friendly

Hassle Free Getaway Beach Front Property, family friendly
St Mary
The price is AU$238
includes taxes & fees
12 Dec - 13 Dec
Hassle Free Getaway Beach Front Property, family friendly
A room with large windows offering a view of a coastal landscape and dense greenery.

15. Dreaming in the Sun Getaway

Dreaming in the Sun Getaway
St. Mary Parish
10.0 out of 10, Exceptional, (1 review)
"This property was an unexpected great find in Robins Bay. Just 3 minutes from the fork in the town. The view of the ocean, the comfortable mattress, the lovely fruit trees and the spacious living room and verandah helped to make our stay a very pleasant one. Aleisha was extremely responsive and her husband Wray and Miss Chunny took care of every detail. The Jamaican breakfast that Chunny made was extremely delicious and it came with a very generous serving of local fruits for a reasonable...
United States
Marva
The price is AU$231
includes taxes & fees
12 Dec - 13 Dec
Dreaming in the Sun Getaway
A bedroom with a bed, a bench, a large mirror, and a view into the kitchen.

16. Serene Super Studio Apartment with porch in Kingston

Serene Super Studio Apartment with porch in Kingston
Havendale
10.0 out of 10, Exceptional, (5 reviews)
"The host was very responsive and accommodating from the point of checking in until check out. The place was clean and it was just as described in the photos."
United States
Kimberley
The price is AU$212
includes taxes & fees
12 Dec - 13 Dec
Serene Super Studio Apartment with porch in Kingston
balcony

17. Low, Low Rate, Very Affordable Cottage on Private White Sand Beach

Low, Low Rate, Very Affordable Cottage on Private White Sand Beach
St. Mary
The price is AU$348
includes taxes & fees
12 Dec - 13 Dec
Low, Low Rate, Very Affordable Cottage on Private White Sand Beach
A modern indoor swimming pool with glass walls, a wooden deck, and a multi-level building with balconies and hanging lights.

18. Apartment with roof top pool

Apartment with roof top pool
2.0 star property
Half Way Tree
6.8 out of 10, (11 reviews)
"Rooms were excellent, really loved the roof was a beautiful view. People were friendly and kind couldnt have asked for a better stay!!"
United States
Jacqueline
The price is AU$556
includes taxes & fees
12 Dec - 13 Dec
Apartment with roof top pool
Beach

19. Standard Dorm Style Cottage Ocean View Affordable Accommodation Living 4 persons

Standard Dorm Style Cottage Ocean View Affordable Accommodation Living 4 persons
St. Mary
The price is AU$203
includes taxes & fees
12 Dec - 13 Dec
Standard Dorm Style Cottage Ocean View Affordable Accommodation Living 4 persons
A modern living room with a black leather sofa, a small table with a vase, and a TV mounted on a blue wall.

20. Camrose by the Curve Meadowbrook 2-bedroom Apt in Meadowbrook, Kingston

Camrose by the Curve Meadowbrook 2-bedroom Apt in Meadowbrook, Kingston
Kingston
9.4 out of 10, Exceptional, (3 reviews)
"My husband and I enjoyed our stay it was nice and clean and comfortable "
United States
Lashanette D.
The price is AU$238
includes taxes & fees
8 Dec - 9 Dec
Camrose by the Curve Meadowbrook 2-bedroom Apt in Meadowbrook, Kingston
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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Find holiday rentals that suit your style

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Top Castleton Hotel Reviews

A resort with a clear pool, palm trees, and a view of the mountains.
Strawberry Hill

Strawberry Hill

Strawberry Hill
Irish Town

10/10 Excellent

Lively proprty but has seen better days. Its starting to look its age. It urgentlyrequires TLC. We had the best massage
Australia
ROY
Reviewed April 15, 2026
Strawberry Hill

Find out more about Castleton

Everything you need to know about Castleton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Castleton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Castleton holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Castleton holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Castleton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Castleton holiday rentals we have selected for you start as low as AU$113 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Castleton rentals

At Expedia, we put the best Castleton holiday 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 Castleton 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 Castleton holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castleton. 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

Are there holiday rentals in Castleton?

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

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

Phoenix Park Villas Portmore: This holiday home rental outside of Castleton offers a private balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave.

What can I see and do in Castleton?

Blue and John Crow Mountains National Park and Castleton Gardens are a couple of lovely local spots to get outside and enjoy nature. Manor Park Plaza and Jamaica House are a couple of places you'll find in the wider area.

What are holiday rentals like in Castleton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Castleton. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.