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Castleton 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 Castleton vacation 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
$76 nightly
The price is $88
Sep 24 - Sep 25
Total with taxes and fees
Tapioca Village Retreat
A wooden deck with a table and chairs, surrounded by lush greenery and a view of distant mountains.

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
$127 nightly
The price is $147
Sep 24 - Sep 25
Total with taxes and fees
Reggae Legends Estate
A rectangular swimming pool with a metal safety railing, surrounded by a concrete deck and a green wall.

3. 1BR Comfort City Apartment with pool

1BR Comfort City Apartment with pool
2.0 star property
Kingston
$251 nightly
The price is $290
Sep 24 - Sep 25
Total with taxes and fees
1BR Comfort City Apartment with pool
A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

4. 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
$290 nightly
The price is $334
Sep 24 - Sep 25
Total with taxes and fees
Phoenix Park Villas Portmore
A room with large windows offering a view of a coastal landscape and dense greenery.

5. 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
$165 nightly
The price is $165
Sep 24 - Sep 25
Total with taxes and fees
Dreaming in the Sun Getaway
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.

6. 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
$86 nightly
The price is $87
Oct 1 - Oct 2
Total with taxes and fees
The Gardens
A modern living room with a sofa, coffee table, and television.

7. Urban Charm: Modern One Bedroom

Urban Charm: Modern One Bedroom
New Kingston
9.4 out of 10, Exceptional, (14 reviews)
"Absolutely beautiful and helpful property owners. Looking forward to staying again."
United States
Colin
$147 nightly
The price is $147
Sep 28 - Sep 29
Total with taxes and fees
Urban Charm: Modern One Bedroom
A wooden bed with intricate carvings, a bedside lamp, and a robe hanging on the wall.

8. Windbreak Villa

Windbreak Villa
3.5 star property
Buff Bay
10.0 out of 10, Exceptional, (1 review)
$84 nightly
The price is $97
Sep 24 - Sep 25
Total with taxes and fees
Windbreak Villa
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
$251 nightly
The price is $289
Sep 24 - Sep 25
Total with taxes and fees
Magical Romantic Getaway For 2, Lovers Paradise On Private White Sand Beach Cove

10. Tropical Tranquility and "Secluded Bliss: Dream Maker Hideaway"

Tropical Tranquility and "Secluded Bliss: Dream Maker Hideaway"
Robins Bay
$251 nightly
The price is $289
Sep 24 - Sep 25
Total with taxes and fees
Tropical Tranquility and "Secluded Bliss: Dream Maker Hideaway"
A wooden deck with a hammock, a wooden table, and a view of the ocean.

11. Special Low Rate, Tranquil Soaking Tub on Roof Overlooking Turquoise Beach

Special Low Rate, Tranquil Soaking Tub on Roof Overlooking Turquoise Beach
St Mary
$285 nightly
The price is $329
Sep 24 - Sep 25
Total with taxes and fees
Special Low Rate, Tranquil Soaking Tub on Roof Overlooking Turquoise Beach

12. Discounted New! Tranquil, Luxurious 2 Bedroom, Oceanfront Villa in Paradise

Discounted New! Tranquil, Luxurious 2 Bedroom, Oceanfront Villa in Paradise
Robins Bay
$320 nightly
The price is $370
Sep 26 - Sep 27
Total with taxes and fees
Discounted New! Tranquil, Luxurious 2 Bedroom, Oceanfront Villa in Paradise
A balcony with a view of a swimming pool and a mountainous landscape.

13. Braata @ Little Bay (Ocean View Villa)

Braata @ Little Bay (Ocean View Villa)
Port Maria
9.6 out of 10, Exceptional, (4 reviews)
"Very nice property Clean and spacious Staff was responsive Only issue was the Ac giving issues but it was sorted eventually Toilets a bit hard to flush However I would return here as it was a pleasant stay"
United States
Anneka
$589 nightly
The price is $589
Sep 24 - Sep 25
Total with taxes and fees
Braata @ Little Bay (Ocean View Villa)
A kitchen with a granite countertop, stainless steel faucet, and a coffee machine.

14. 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
$211 nightly
The price is $243
Sep 24 - Sep 25
Total with taxes and fees
Modern 1BR Condo in Kingston
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.

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
$175 nightly
The price is $195
Sep 24 - Sep 25
Total with taxes and fees
The Cozy Curve: Full 2 Br 2 Bth Apartment in Central location in Kingston

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

Low, Low Rate, Very Affordable Cottage on Private White Sand Beach
St. Mary
$216 nightly
The price is $248
Sep 24 - Sep 25
Total with taxes and fees
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.

17. Apartment with roof top pool

Apartment with roof top pool
2.0 star property
Half Way Tree
7.2 out of 10, Good, (10 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
$330 nightly
The price is $381
Sep 24 - Sep 25
Total with taxes and fees
Apartment with roof top pool
A swimming pool with a clear water surface reflecting surrounding buildings, a covered area with stairs, and a metal railing along the pool's edge.

18. 1BR Premium Apartments Nitram

1BR Premium Apartments Nitram
2.0 star property
Kingston
$291 nightly
The price is $336
Sep 24 - Sep 25
Total with taxes and fees
1BR Premium Apartments Nitram
A wooden staircase leading to a small wooden building with a white door and windows.

19. Jamaica House - The Blue Mountain Wilderness Retreat

Jamaica House - The Blue Mountain Wilderness Retreat
Bangor Ridge
$97 nightly
The price is $97
Sep 24 - Sep 25
Total with taxes and fees
Jamaica House - The Blue Mountain Wilderness Retreat
A swimming pool with a gazebo, a clear sky, and a distant view of buildings.

20. Bayfront apartment and villas

Bayfront apartment and villas
Portmore
10.0 out of 10, Exceptional, (5 reviews)
"Good place to stay"
United States
Kimone
$101 nightly
The price is $101
Sep 27 - Sep 28
Total with taxes and fees
Bayfront apartment and villas
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

R Hotel Kingston

R Hotel Kingston

8/10 Good
"Excellent staff, clean rooms"
David 3-night trip
Posted less than an hour ago
R Hotel Kingston

Find out more about Castleton

Everything you need to know about Castleton 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 Castleton 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 Castleton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castleton vacation 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 low season months. For more hustle and bustle, you may prefer to visit Castleton 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 $87 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 Castleton rentals

At Expedia, we put the best Castleton 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 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 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 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.

Explore a world of travel with Expedia

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.