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Castleton Vacation Rentals

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Our top choices for Castleton vacation 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 CA $98
CA $114 total
includes taxes & fees
Nov 3 - Nov 4
Tapioca Village Retreat

2. 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 CA $82
CA $145 total
includes taxes & fees
Oct 9 - Oct 10
Abacus Jamaica the Zana Suite

3. 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 CA $200
CA $231 total
includes taxes & fees
Oct 9 - Oct 10
Reggae Legends Estate

4. The Gardens

The Gardens
3.0 star property
Barbican
7.8 out of 10, Good, (68 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 CA $118
CA $119 total
includes taxes & fees
Oct 8 - Oct 9
The Gardens

5. Windbreak Villa

Windbreak Villa
3.5 star property
Buff Bay
10.0 out of 10, Exceptional, (1 review)
The price is CA $119
CA $139 total
includes taxes & fees
Oct 4 - Oct 5
Windbreak Villa

6. Urban Charm: Modern One Bedroom

Urban Charm: Modern One Bedroom
New Kingston
9.4 out of 10, Exceptional, (15 reviews)
"Absolutely beautiful and helpful property owners. Looking forward to staying again."
United States
Colin
The price is CA $134
CA $220 total
includes taxes & fees
Oct 10 - Oct 11
Urban Charm: Modern One Bedroom

7. 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 CA $90
CA $118 total
includes taxes & fees
Oct 4 - Oct 5
Cozy studio apartment with queen bed in charming Kingston with AC

8. 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 CA $136
CA $221 total
includes taxes & fees
Oct 4 - Oct 5
Camrose by the Curve Meadowbrook 2-bedroom Apt in Meadowbrook, Kingston

9. 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 CA $206
CA $235 total
includes taxes & fees
Oct 4 - Oct 5
Dreaming in the Sun Getaway

10. 1BR Comfort City Apartment with pool

1BR Comfort City Apartment with pool
2.0 star property
Kingston
The price is CA $228
CA $412 total
includes taxes & fees
Oct 5 - Oct 6
1BR Comfort City Apartment with pool

11. Hassle Free Getaway Beach Front Property, family friendly

Hassle Free Getaway Beach Front Property, family friendly
St Mary
The price is CA $142
CA $242 total
includes taxes & fees
Oct 4 - Oct 5
Hassle Free Getaway Beach Front Property, family friendly

12. 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 CA $156
CA $346 total
includes taxes & fees
Oct 4 - Oct 5
Modern 1BR Condo in Kingston

13. Jamaica House - The Blue Mountain Wilderness Retreat

Jamaica House - The Blue Mountain Wilderness Retreat
Bangor Ridge
The price is CA $100
CA $138 total
includes taxes & fees
Oct 4 - Oct 5
Jamaica House - The Blue Mountain Wilderness Retreat

14. 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 CA $114
CA $208 total
includes taxes & fees
Oct 4 - Oct 5
Standard Dorm Style Cottage Ocean View Affordable Accommodation Living 4 persons

15. 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 CA $88
CA $159 total
includes taxes & fees
Oct 4 - Oct 5
Cozy 1-bedroom house, Molynes Road. Perfect for a peaceful getaway on a budget

16. Bayfront apartment and villas

Bayfront apartment and villas
Portmore
10.0 out of 10, Exceptional, (6 reviews)
"Good place to stay"
United States
Kimone
The price is CA $87
CA $144 total
includes taxes & fees
Oct 6 - Oct 7
Bayfront apartment and villas

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

Cozy 1-bedroom apartment in welcoming Kingston with AC
Kingston
The price is CA $102
CA $223 total
includes taxes & fees
Oct 14 - Oct 15
Cozy 1-bedroom apartment in welcoming Kingston with AC

18. 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 CA $228
CA $350 total
includes taxes & fees
Oct 4 - Oct 5
Low, Low Rate, Very Affordable Cottage on Private White Sand Beach

19. Braeton Pointe

Braeton Pointe
3.0 star property
Portmore
The price is CA $68
CA $107 total
includes taxes & fees
Oct 4 - Oct 5
Braeton Pointe

20. Serene Super Studio Apartment with porch in Kingston

Serene Super Studio Apartment with porch in Kingston
Havendale
10.0 out of 10, Exceptional, (3 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 CA $121
CA $182 total
includes taxes & fees
Oct 4 - Oct 5
Serene Super Studio Apartment with porch in 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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Top Castleton Hotel Reviews

Find out more about Castleton

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Castleton?

Yes, we offer vacation rentals near top points of interest in Castleton, or you can choose a more secluded option if you want a relaxing place to stay. Castleton is known for its parks.

What are some of the best vacation rentals in Castleton?

Phoenix Park Villas Portmore: This vacation 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 larger area.

What are vacation rentals like in Castleton?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Castleton. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.