Cheap Vacations in Trelawny

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Trelawny vacations

Price found within the past 48 hours. Click for updated prices.
Ocean Coral Spring - All Inclusive

Ocean Coral Spring - All Inclusive

5 out of 5
Save 100% on your flight
Price was $2,310, price is now $1,221 per person
$1,221
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Hotel Riu Palace Tropical Bay - All Inclusive

Hotel Riu Palace Tropical Bay - All Inclusive

4 out of 5
Price was $7,335, price is now $3,744 per person
$3,744
per person
Dec 9 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

5 out of 5
Price was $3,338, price is now $1,730 per person
$1,730
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

5 out of 5
Save 100% on your flight
Price was $2,805, price is now $1,468 per person
$1,468
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Princess Senses The Mangrove Resort - Luxury Adults Only - All Inclusive

Princess Senses The Mangrove Resort - Luxury Adults Only - All Inclusive

5 out of 5
Price was $4,122, price is now $2,172 per person
$2,172
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Price was $2,748, price is now $1,464 per person
$1,464
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

5 out of 5
Price was $16,454, price is now $8,787 per person
$8,787
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Montego Bay (MBJ)
Ocho Rios Villa at the Palms VII

Ocho Rios Villa at the Palms VII

3 out of 5
Save 100% on your flight
Price was $3,038, price is now $1,648 per person
$1,648
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Montego Bay (MBJ)
Ocho Rios Villa at the Palms II

Ocho Rios Villa at the Palms II

3.5 out of 5
Save 100% on your flight
Price was $2,412, price is now $1,309 per person
$1,309
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocho Rios Getaway Villa at Draxhall

Ocho Rios Getaway Villa at Draxhall

3.5 out of 5
Save 100% on your flight
Price was $2,322, price is now $1,307 per person
$1,307
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Montego Bay (MBJ)

3-night Trelawny vacations

Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at Coolshade III

Ocho Rios Villa at Coolshade III

2.5 out of 5
Price was $1,129, price is now $718 per person
$718
per person
Dec 1 - Dec 4
found 9 hours ago
Roundtrip flight included
New York (JFK) to Montego Bay (MBJ)
Hotel Riu Palace Tropical Bay - All Inclusive

Hotel Riu Palace Tropical Bay - All Inclusive

4 out of 5
Price was $3,288, price is now $1,743 per person
$1,743
per person
Dec 7 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

5 out of 5
Save 100% on your flight
Price was $2,145, price is now $1,157 per person
$1,157
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

5 out of 5
Price was $7,389, price is now $4,027 per person
$4,027
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

4.5 out of 5
Save 100% on your flight
Price was $2,248, price is now $1,251 per person
$1,251
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocean Coral Spring - All Inclusive

Ocean Coral Spring - All Inclusive

5 out of 5
Price was $1,883, price is now $1,066 per person
$1,066
per person
Dec 11 - Dec 14
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Princess Senses The Mangrove Resort - Luxury Adults Only - All Inclusive

Princess Senses The Mangrove Resort - Luxury Adults Only - All Inclusive

5 out of 5
Save 100% on your flight
Price was $2,345, price is now $1,370 per person
$1,370
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Hotel Riu Palace Aquarelle - All Inclusive

Hotel Riu Palace Aquarelle - All Inclusive

4 out of 5
Save 100% on your flight
Price was $2,202, price is now $1,314 per person
$1,314
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
Price was $1,636, price is now $997 per person
$997
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Hotel Riu Negril - All Inclusive

Hotel Riu Negril - All Inclusive

4 out of 5
Price was $1,374, price is now $844 per person
$844
per person
Dec 7 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Save 100% on your flight
Price was $1,935, price is now $1,200 per person
$1,200
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Hotel Riu Reggae - Adults Only - All Inclusive

Hotel Riu Reggae - Adults Only - All Inclusive

4 out of 5
Price was $1,503, price is now $955 per person
$955
per person
Dec 7 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)

4-night Trelawny vacations

Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at Coolshade VI

Ocho Rios Villa at Coolshade VI

3.5 out of 5
Save 100% on your flight
Price was $1,457, price is now $842 per person
$842
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Sunset at the Palms Resort - Adults Only - All Inclusive

Sunset at the Palms Resort - Adults Only - All Inclusive

4.5 out of 5
Price was $2,697, price is now $1,372 per person
$1,372
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

5 out of 5
Save 100% on your flight
Price was $2,805, price is now $1,468 per person
$1,468
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocean Coral Spring - All Inclusive

Ocean Coral Spring - All Inclusive

5 out of 5
Save 100% on your flight
Price was $2,310, price is now $1,221 per person
$1,221
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

5 out of 5
Price was $9,789, price is now $5,318 per person
$5,318
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Princess Senses The Mangrove Resort - Luxury Adults Only - All Inclusive

Princess Senses The Mangrove Resort - Luxury Adults Only - All Inclusive

5 out of 5
Price was $2,711, price is now $1,496 per person
$1,496
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
Save 100% on your flight
Price was $1,956, price is now $1,087 per person
$1,087
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

5 out of 5
Price was $2,527, price is now $1,421 per person
$1,421
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Price was $2,305, price is now $1,336 per person
$1,336
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Hotel Riu Palace Aquarelle - All Inclusive

Hotel Riu Palace Aquarelle - All Inclusive

4 out of 5
Save 100% on your flight
Price was $3,105, price is now $1,802 per person
$1,802
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocho Rios Villa at Coolshade X

Ocho Rios Villa at Coolshade X

3.5 out of 5
Save 100% on your flight
Price was $1,652, price is now $963 per person
$963
per person
Dec 9 - Dec 13
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Ocho Rios Villa at the Palms II

Ocho Rios Villa at the Palms II

3.5 out of 5
Save 100% on your flight
Price was $1,565, price is now $914 per person
$914
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)

5-night Trelawny vacations

Price found within the past 48 hours. Click for updated prices.
Ocho Rios Tranquility at Coolshade VII

Ocho Rios Tranquility at Coolshade VII

3 out of 5
Save 100% on your flight
Price was $1,612, price is now $921 per person
$921
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Ocean Coral Spring - All Inclusive

Ocean Coral Spring - All Inclusive

5 out of 5
Price was $2,704, price is now $1,325 per person
$1,325
per person
Dec 9 - Dec 14
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

5 out of 5
Price was $3,452, price is now $1,715 per person
$1,715
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Hotel Riu Palace Aquarelle - All Inclusive

Hotel Riu Palace Aquarelle - All Inclusive

4 out of 5
Price was $3,079, price is now $1,605 per person
$1,605
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Price was $2,748, price is now $1,464 per person
$1,464
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocho Rios Villa at Coolshade IV

Ocho Rios Villa at Coolshade IV

3.5 out of 5
Price was $1,802, price is now $986 per person
$986
per person
Dec 6 - Dec 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Bahia Principe Explore Jamaica - Hyatt Inclusive Collection - All Inclusive - Totally Refurbished in 2026

Bahia Principe Explore Jamaica - Hyatt Inclusive Collection - All Inclusive - Totally Refurbished in 2026

4 out of 5
Price was $2,407, price is now $1,349 per person
$1,349
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocho Rios Villa Azul at Coolshade XIII

Ocho Rios Villa Azul at Coolshade XIII

3.5 out of 5
Save 100% on your flight
Price was $1,676, price is now $949 per person
$949
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Ocho Rios Villa at the Palms IV

Ocho Rios Villa at the Palms IV

3 out of 5
Save 100% on your flight
Price was $1,672, price is now $947 per person
$947
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Ocho Rios Villa at the Palms II

Ocho Rios Villa at the Palms II

3.5 out of 5
Price was $1,875, price is now $1,073 per person
$1,073
per person
Dec 2 - Dec 7
found 1 day ago
Roundtrip flight included
New York (JFK) to Montego Bay (MBJ)
Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only- Renovated 2026

Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only- Renovated 2026

4.5 out of 5
Price was $2,184, price is now $1,250 per person
$1,250
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
Save 100% on your flight
Price was $2,643, price is now $1,548 per person
$1,548
per person
Dec 16 - Dec 21
found 23 hours ago
Roundtrip flight included
New York (JFK) to Montego Bay (MBJ)

6-7 night Trelawny vacations

Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at Coolshade VI

Ocho Rios Villa at Coolshade VI

3.5 out of 5
Price was $2,123, price is now $1,046 per person
$1,046
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Montego Bay (MBJ)
Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

5 out of 5
Price was $3,623, price is now $1,618 per person
$1,618
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocean Coral Spring - All Inclusive

Ocean Coral Spring - All Inclusive

5 out of 5
Price was $4,397, price is now $1,974 per person
$1,974
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Montego Bay (MBJ)
Hotel Riu Palace Tropical Bay - All Inclusive

Hotel Riu Palace Tropical Bay - All Inclusive

4 out of 5
Price was $7,335, price is now $3,744 per person
$3,744
per person
Dec 9 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Retreat Plantation House

Retreat Plantation House

3 out of 5
Save 100% on your flight
Price was $2,255, price is now $1,153 per person
$1,153
per person
Nov 29 - Dec 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

5 out of 5
Price was $3,338, price is now $1,730 per person
$1,730
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocho Rios Villa at the Palms III

Ocho Rios Villa at the Palms III

3.5 out of 5
Save 100% on your flight
Price was $2,087, price is now $1,087 per person
$1,087
per person
Nov 29 - Dec 5
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Hotel Riu Palace Aquarelle - All Inclusive

Hotel Riu Palace Aquarelle - All Inclusive

4 out of 5
Price was $3,845, price is now $2,007 per person
$2,007
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Princess Senses The Mangrove Resort - Luxury Adults Only - All Inclusive

Princess Senses The Mangrove Resort - Luxury Adults Only - All Inclusive

5 out of 5
Price was $4,122, price is now $2,172 per person
$2,172
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

5 out of 5
Price was $16,454, price is now $8,787 per person
$8,787
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Montego Bay (MBJ)
Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Price was $3,210, price is now $1,737 per person
$1,737
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocho Rios Villa at the Palms VII

Ocho Rios Villa at the Palms VII

3 out of 5
Save 100% on your flight
Price was $3,038, price is now $1,648 per person
$1,648
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Montego Bay (MBJ)

Top places to visit in Trelawny

A beach with clear turquoise waters, a pier extending into the sea, and a hotel with palm trees in the background.
FlightsFlightsHotelsHotels

Falmouth

Falmouth

Flight deals to Trelawny

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Mon, Jan 18 - Sun, Jan 24
YYZ
Toronto
MBJ
Montego Bay
$245 Roundtrip, found 5 hours ago
$245
Roundtrip
found 5 hours ago
Select Flair Airlines flight, departing Mon, Jan 18 from Toronto to Montego Bay, returning Sun, Jan 24, priced at $245 found 5 hours ago
Sun, Nov 15 - Thu, Nov 19
ATL
Atlanta
MBJ
Montego Bay
$344 Roundtrip, found 14 hours ago
$344
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sun, Nov 15 from Atlanta to Montego Bay, returning Thu, Nov 19, priced at $344 found 14 hours ago
Tue, Nov 17 - Fri, Nov 20
EWR
New York
MBJ
Montego Bay
$358 Roundtrip, found 7 hours ago
$358
Roundtrip
found 7 hours ago
Select United flight, departing Tue, Nov 17 from New York to Montego Bay, returning Fri, Nov 20, priced at $358 found 7 hours ago

Top rated hotels for your Trelawny vacation

Hotel Riu Palace Aquarelle - All Inclusive

Hotel Riu Palace Aquarelle - All Inclusive

4 out of 5
Falmouth Falmouth
9.43 mi from city center
Get rates
With a stay at Hotel Riu Palace Aquarelle - All Inclusive in Falmouth (Falmouth Historic Town Centre), you'll be steps from Water Square and a 2-minute drive from Martha Brae River.
Pool
Breakfast included
Excellence Oyster Bay - Adults Only All Inclusive

Excellence Oyster Bay - Adults Only All Inclusive

5 out of 5
Peninsula Oyster Bay Falmouth
9.1 mi from city center
Get rates
Located in Falmouth, Excellence Oyster Bay - Adults Only All Inclusive is by the ocean, within a 10-minute drive of Luminous Lagoon and Martha Brae River.
On private beach
Pool
Ocean Coral Spring - All Inclusive

Ocean Coral Spring - All Inclusive

5 out of 5
Mountain Spring Bay Falmouth 07
8.89 mi from city center
$343 nightly
The price is $382 total per night
$382 total
Nov 1 - Nov 2
Total with taxes and fees
Located in Falmouth, Ocean Coral Spring - All Inclusive is by the ocean, within a 15-minute drive of Luminous Lagoon and Burwood Beach.
On private beach
Pool
Don't see what you're looking for?
See all available properties in Trelawny
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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.

Top Picks

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.