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Search and Rent Jamaica Condos

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Our top choices for Jamaica condo rentals

Property grounds
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.0 out of 10, Wonderful, (45)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
$272 nightly
The price is $307
Jan 14 - Jan 15, 2026
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Property grounds
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
$284 nightly
The price is $321
Jan 11 - Jan 12, 2026
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Fridge, microwave, oven, stovetop
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (53)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
$345 nightly
The price is $390
Jan 14 - Jan 15, 2026
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
$404 nightly
The price is $457
Jan 21 - Jan 22, 2026
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi

Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi

Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
Clock Tower Base Area
8.6 out of 10, Excellent, (14)
"Excellent Location.. "
United States
Juan Carlos L.
$332 nightly
The price is $375
Jan 26 - Jan 27, 2026
Total with taxes and fees
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
Microwave, oven, stovetop, dishwasher
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
10.0 out of 10, Exceptional, (102)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
$324 nightly
The price is $354
Jan 12 - Jan 13, 2026
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
TV, DVD player
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (26)
"Loved the location"
United States
Steven W.
$295 nightly
The price is $333
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Exterior
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

2nd-floor downtown Ludlow studio condo with kitchenette, streaming

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Ludlow
8.6 out of 10, Excellent, (4)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
$275 nightly
The price is $310
Jan 5 - Jan 6, 2026
Total with taxes and fees
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Property grounds
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Clock Tower Base Area
9.4 out of 10, Exceptional, (22)
"Enjoy our stay !!!!! Awesome in and out right on the slope feet away for deck."
United States
Dan G.
$391 nightly
The price is $441
Jan 6 - Jan 7, 2026
Total with taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Terrace/patio
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
7.4 out of 10, Good, (20)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
$385 nightly
The price is $435
Jan 7 - Jan 8, 2026
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Microwave, oven, stovetop, coffee/tea maker
Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Ludlow
9.0 out of 10, Wonderful, (14)
"Great location and very comfortable."
United States
Richard J.
$325 nightly
The price is $367
Jan 12 - Jan 13, 2026
Total with taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Interior
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (22)
"Great rate for a place with all the basics!"
United States
Macgregor
$275 nightly
The price is $310
Jan 5 - Jan 6, 2026
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Exterior
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (19)
"Amazing place! "
United States
Tara
$481 nightly
The price is $539
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
TV, fireplace
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.6 out of 10, Excellent, (27)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
United States
John N.
$413 nightly
The price is $466
Jan 28 - Jan 29, 2026
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Dining
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.8 out of 10, Exceptional, (16)
"Perfect spot to jump onto the mountain and ski. Two adults and 4 kids, and we had plenty of space for a long weekend."
United States
Allison T.
$855 nightly
The price is $966
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Interior
Stratton Mtn Studio | Renovated | Walk to Lifts

Stratton Mtn Studio | Renovated | Walk to Lifts

Stratton Mtn Studio | Renovated | Walk to Lifts
Stratton Mountain
10.0 out of 10, Exceptional, (30)
"Great location."
United States
Jeffrey
$635 nightly
The price is $718
Jan 5 - Jan 6, 2026
Total with taxes and fees
Stratton Mtn Studio | Renovated | Walk to Lifts
Interior
Perfect location for your next Vermont Getaway!

Perfect location for your next Vermont Getaway!

Perfect location for your next Vermont Getaway!
Stratton
9.2 out of 10, Wonderful, (5)
"Perfect location and nice condo"
United States
Doug M.
$834 nightly
The price is $920
Jan 6 - Jan 7, 2026
Total with taxes and fees
Perfect location for your next Vermont Getaway!
Exterior
Chic Condo <1 Mile Away from Stratton’s Village

Chic Condo <1 Mile Away from Stratton’s Village

Chic Condo <1 Mile Away from Stratton’s Village
2.0 star property
Stratton
$957 nightly
The price is $1,081
Jan 1 - Jan 2, 2026
Total with taxes and fees
Chic Condo <1 Mile Away from Stratton’s Village
Property grounds
OKEMO WINTERPLACE Best Location, Ski-In/Ski-Out 4BR/3BATH + LOFT. Spacious.

OKEMO WINTERPLACE Best Location, Ski-In/Ski-Out 4BR/3BATH + LOFT. Spacious.

OKEMO WINTERPLACE Best Location, Ski-In/Ski-Out 4BR/3BATH + LOFT. Spacious.
Okemo Village
10.0 out of 10, Exceptional, (13)
"The condo is great for ski in ski out"
United States
Nanette P.
$1,341 nightly
The price is $1,515
Jan 19 - Jan 20, 2026
Total with taxes and fees
OKEMO WINTERPLACE Best Location, Ski-In/Ski-Out 4BR/3BATH + LOFT. Spacious.
Smart TV, fireplace, books, stereo
Okemo Ridge Retreat - Slopeside 3-bdrm with Sauna. Steps to Kettlebrook Trail.

Okemo Ridge Retreat - Slopeside 3-bdrm with Sauna. Steps to Kettlebrook Trail.

Okemo Ridge Retreat - Slopeside 3-bdrm with Sauna. Steps to Kettlebrook Trail.
2.0 star property
Ludlow
$948 nightly
The price is $1,071
Jan 22 - Jan 23, 2026
Total with taxes and fees
Okemo Ridge Retreat - Slopeside 3-bdrm with Sauna. Steps to Kettlebrook Trail.
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 Jamaica Hotel Reviews

Chalet 239

Chalet 239

10/10 Excellent
"It was great! Would stay here again, loved the TV and fiended when we saw there was a hot chocolate machine. Totally recommend, nice people and super close to the slopes so we could wake up late."
Stella 3-night trip
Posted 3 days ago
Chalet 239

Find out more about Jamaica

Jamaica Condo Rentals information

Number of reviews
404
Accommodation
362 Condo Rentals
Lowest Price
$307
Highest Price
$1,515

Frequently asked questions

How much do condos in Jamaica cost?
The price range for condos in Jamaica is $307 to $1,515 per night. Whatever your budget, you're sure to find a place that suits your wallet — as well as your whole family! These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Jamaica?
Pick from 362 condos in Jamaica. No matter if you're traveling with the little ones or organizing a weekend break with your besties, Expedia will help you find the right space for your crew.
Why book your condo in Jamaica with Expedia?
Booking a condo in Jamaica is as simple as deciding on your travel dates and picking an option that satisfies your needs. Looking for something luxurious or affordable, or a property that also has a pool and a hot tub? Use Expedia's search filters to further narrow your search results and find the ideal fit.
How can I find cheap condos in Jamaica?
Expedia can help you locate cheap condos in Jamaica. To book your special stay in a few quick clicks, try out our convenient filter tool to refine your search by star rating, budget and amenities.
What is there to do in Jamaica near my condo?
If you want to discover the sights of Jamaica, don't miss Jamaica State Park. It's a hit among locals and travelers alike.

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