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Castleton Holiday Rentals

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Our top choices for Castleton holiday rentals

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 NZ$163
includes taxes & fees
21 Sept - 22 Sept
Tapioca Village Retreat

2. 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 NZ$284
includes taxes & fees
21 Sept - 22 Sept
Reggae Legends Estate

3. Windbreak Villa

Windbreak Villa
3.5 star property
Buff Bay
10.0 out of 10, Exceptional, (1 review)
The price is NZ$170
includes taxes & fees
21 Sept - 22 Sept
Windbreak Villa

4. 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 NZ$288
includes taxes & fees
21 Sept - 22 Sept
Dreaming in the Sun Getaway

5. The Gardens

The Gardens
3.0 star property
Barbican
7.8 out of 10, Good, (67 reviews)
"The place was very clean, the bed was comfortable and the bathroom was very modern. Loved the place!"
United States
Jelani
The price is NZ$168
includes taxes & fees
21 Sept - 22 Sept
The Gardens

6. Urban Charm: Modern One Bedroom

Urban Charm: Modern One Bedroom
New Kingston
9.4 out of 10, Exceptional, (14 reviews)
"Absolutely beautiful and helpful property owners. Looking forward to staying again."
United States
Colin
The price is NZ$270
includes taxes & fees
21 Sept - 22 Sept
Urban Charm: Modern One Bedroom

7. Cozy 1-bedroom house, Molynes Road. Perfect for a peaceful getaway on a budget

Cozy 1-bedroom house, Molynes Road. Perfect for a peaceful getaway on a budget
Ziadie Gardens
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and the place was exactly as described. Hospitality was a 10/10. It was certainly a home away from home vibe."
Canada
Sharon
The price is NZ$195
includes taxes & fees
21 Sept - 22 Sept
Cozy 1-bedroom house, Molynes Road. Perfect for a peaceful getaway on a budget

8. Jamaica House - The Blue Mountain Wilderness Retreat

Jamaica House - The Blue Mountain Wilderness Retreat
Bangor Ridge
The price is NZ$170
includes taxes & fees
21 Sept - 22 Sept
Jamaica House - The Blue Mountain Wilderness Retreat

9. 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 NZ$160
includes taxes & fees
3 Oct - 4 Oct
Cozy studio apartment with queen bed in charming Kingston with AC

10. Cozy 1-bedroom apartment in welcoming Kingston with AC

Cozy 1-bedroom apartment in welcoming Kingston with AC
Kingston
The price is NZ$274
includes taxes & fees
21 Sept - 22 Sept
Cozy 1-bedroom apartment in welcoming Kingston with AC

11. Bayfront apartment and villas

Bayfront apartment and villas
Portmore
10.0 out of 10, Exceptional, (5 reviews)
"Good place to stay"
United States
Kimone
The price is NZ$177
includes taxes & fees
21 Sept - 22 Sept
Bayfront apartment and villas

12. Abacus Jamaica the Zana Suite

Abacus Jamaica the Zana Suite
3.0 star property
Constant Spring
7.8 out of 10, Good, (74 reviews)
"This was the worst rental I've ever had . I reserved"
United States
Teri
The price is NZ$178
includes taxes & fees
1 Oct - 2 Oct
Abacus Jamaica the Zana Suite

13. 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 NZ$430
includes taxes & fees
21 Sept - 22 Sept
Low, Low Rate, Very Affordable Cottage on Private White Sand Beach

14. Caldo Tours

Caldo Tours
2.5 star property
Ewarton
10.0 out of 10, Exceptional, (3 reviews)
"Very inviting and the owner's are wonderful people that keeps you comfortable and satisfied "
United States
Stephen
The price is NZ$227
includes taxes & fees
21 Sept - 22 Sept
Caldo Tours

15. 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 price is NZ$342
includes taxes & fees
21 Sept - 22 Sept
The Cozy Curve: Full 2 Br 2 Bth Apartment in Central location in Kingston

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

Camrose by the Curve Meadowbrook 2-bedroom Apt in Meadowbrook, Kingston
Kingston
10.0 out of 10, Exceptional, (2 reviews)
"My husband and I enjoyed our stay it was nice and clean and comfortable "
United States
Lashanette D.
The price is NZ$272
includes taxes & fees
4 Oct - 5 Oct
Camrose by the Curve Meadowbrook 2-bedroom Apt in Meadowbrook, Kingston

17. Phoenix Park Villas Portmore

Phoenix Park Villas Portmore
4.0 star property
Portmore
9.8 out of 10, Exceptional, (6 reviews)
"I will definitely recommend that you stay here is so peaceful security are strictly on point with everything and the comfort of the home is great will be staying back for sure ."
United States
Kimoya
The price is NZ$585
includes taxes & fees
21 Sept - 22 Sept
Phoenix Park Villas Portmore

18. Hassle Free Getaway Beach Front Property, family friendly

Hassle Free Getaway Beach Front Property, family friendly
St Mary
The price is NZ$297
includes taxes & fees
27 Sept - 28 Sept
Hassle Free Getaway Beach Front Property, family friendly

19. Wave Crest Resort Race Course

Wave Crest Resort Race Course
2.5 star property
Oracabessa
The price is NZ$119
includes taxes & fees
21 Sept - 22 Sept
Wave Crest Resort Race Course

20. 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 NZ$255
includes taxes & fees
27 Sept - 28 Sept
Standard Dorm Style Cottage Ocean View Affordable Accommodation Living 4 persons
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 Castleton Hotel Reviews

Find out more about Castleton

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 Castleton 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 Castleton. 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 Castleton. Seeing all the best attractions is bound to make you fall in love with Castleton. 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 Castleton short-term rentals, that won’t be hard to do.

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 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.