Cheap Vacations in Westmoreland

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Westmoreland vacations

Price found within the past 48 hours. Click for updated prices.
Sea Castle Vacation Villa

Sea Castle Vacation Villa

3.5 out of 5
Save 100% on your flight
Price was $1,827, price is now $1,076 per person
$1,076
per person
Dec 2 - 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 $3,104, price is now $1,458 per person
$1,458
per person
Dec 9 - Dec 15
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 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 $2,779, price is now $1,472 per person
$1,472
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip 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 $2,316, price is now $1,250 per person
$1,250
per person
Dec 2 - Dec 7
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 $2,155, price is now $1,167 per person
$1,167
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 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)
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 $2,909, price is now $1,608 per person
$1,608
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,714, price is now $1,520 per person
$1,520
per person
Dec 9 - 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
Save 100% on your flight
Price was $3,121, price is now $1,817 per person
$1,817
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Montego Bay (MBJ)

3-night Westmoreland 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 $1,141, price is now $695 per person
$695
per person
Nov 30 - Dec 3
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 $2,155, price is now $1,167 per person
$1,167
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 19 hours 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 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Hotel Riu Palace Tropical Bay - All Inclusive

Hotel Riu Palace Tropical Bay - All Inclusive

4 out of 5
Price was $1,855, price is now $1,070 per person
$1,070
per person
Nov 30 - Dec 3
found 1 day 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
Price was $2,371, price is now $1,397 per person
$1,397
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)
Ocho Rios Villa at Coolshade

Ocho Rios Villa at Coolshade

3.5 out of 5
Price was $1,185, price is now $706 per person
$706
per person
Nov 30 - Dec 3
found 1 day 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
Save 100% on your flight
Price was $2,212, price is now $1,324 per person
$1,324
per person
Nov 27 - Nov 30
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 $2,022, price is now $1,214 per person
$1,214
per person
Dec 10 - 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
Price was $1,636, price is now $997 per person
$997
per person
Dec 10 - Dec 13
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Ocho Rios Villa at The Palms VI

Ocho Rios Villa at The Palms VI

3.5 out of 5
Price was $1,173, price is now $730 per person
$730
per person
Nov 30 - Dec 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)

4-night Westmoreland vacations

Price found within the past 48 hours. Click for updated prices.
Ocho Rios TaylorMade Vacation Villas

Ocho Rios TaylorMade Vacation Villas

3.5 out of 5
Price was $1,291, price is now $789 per person
$789
per person
Nov 30 - Dec 4
found 21 hours ago
Roundtrip flight included
New York (JFK) 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 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 $2,779, price is now $1,472 per person
$1,472
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip 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
Price was $2,914, price is now $1,580 per person
$1,580
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip 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 $2,909, price is now $1,608 per person
$1,608
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip 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 19 hours 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 19 hours 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 $2,480, price is now $1,433 per person
$1,433
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Montego Bay (MBJ)
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)
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)
Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Price was $2,326, price is now $1,367 per person
$1,367
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip 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
Price was $1,388, price is now $834 per person
$834
per person
Nov 30 - Dec 4
found 21 hours ago
Roundtrip flight included
New York (JFK) to Montego Bay (MBJ)

5-night Westmoreland 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
Price was $1,609, price is now $943 per person
$943
per person
Dec 1 - Dec 6
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
Price was $3,547, price is now $1,602 per person
$1,602
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $2,316, price is now $1,250 per person
$1,250
per person
Dec 2 - Dec 7
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 $2,952, price is now $1,634 per person
$1,634
per person
Nov 28 - Dec 3
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
Save 100% on your flight
Price was $2,735, price is now $1,542 per person
$1,542
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Montego Bay (MBJ)
Ocho Rios Villa at Coolshade VI

Ocho Rios Villa at Coolshade VI

3.5 out of 5
Price was $1,745, price is now $988 per person
$988
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Hotel Riu Palace Tropical Bay - All Inclusive

Hotel Riu Palace Tropical Bay - All Inclusive

4 out of 5
Save 100% on your flight
Price was $3,121, price is now $1,817 per person
$1,817
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Montego Bay (MBJ)
Sea Castle Vacation Villa

Sea Castle Vacation Villa

3.5 out of 5
Save 100% on your flight
Price was $1,827, price is now $1,076 per person
$1,076
per person
Dec 2 - Dec 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)
Ocho Rios Villa at the Palms VII

Ocho Rios Villa at the Palms VII

3 out of 5
Price was $2,055, price is now $1,234 per person
$1,234
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $3,405, price is now $2,055 per person
$2,055
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip non-stop 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 $2,033, price is now $1,238 per person
$1,238
per person
Dec 2 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Montego Bay (MBJ)

6-7 night Westmoreland 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 $3,979, price is now $1,597 per person
$1,597
per person
Dec 9 - Dec 15
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 $3,640, price is now $1,640 per person
$1,640
per person
Nov 26 - Dec 2
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 $3,780, price is now $1,720 per person
$1,720
per person
Nov 26 - Dec 2
found 22 hours 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 $3,104, price is now $1,458 per person
$1,458
per person
Dec 9 - Dec 15
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 $3,868, price is now $1,839 per person
$1,839
per person
Dec 9 - Dec 15
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 $3,506, price is now $1,745 per person
$1,745
per person
Dec 9 - Dec 15
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 $3,148, price is now $1,593 per person
$1,593
per person
Dec 9 - 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)
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 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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)

Top places to visit in Westmoreland

A coastal cliff with a clear blue sea, a small boat, and a thatched-roof structure.
FlightsFlightsHotelsHotels

Negril

Negril

Flight deals to Westmoreland

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

Fri, Jan 15 - Wed, Jan 20
YYZ
Toronto
MBJ
Montego Bay
$283 Roundtrip, found 3 hours ago
$283
Roundtrip
found 3 hours ago
Select WestJet flight, departing Fri, Jan 15 from Toronto to Montego Bay, returning Wed, Jan 20, priced at $283 found 3 hours ago
Sun, Nov 15 - Thu, Nov 19
ATL
Atlanta
MBJ
Montego Bay
$344 Roundtrip, found 6 hours ago
$344
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sun, Nov 15 from Atlanta to Montego Bay, returning Thu, Nov 19, priced at $344 found 6 hours ago
Tue, Nov 17 - Fri, Nov 20
EWR
New York
MBJ
Montego Bay
$358 Roundtrip, found 3 hours ago
$358
Roundtrip
found 3 hours ago
Select United flight, departing Tue, Nov 17 from New York to Montego Bay, returning Fri, Nov 20, priced at $358 found 3 hours ago

Top rated hotels for your Westmoreland vacation

CocoLaPalm Seaside Resort

CocoLaPalm Seaside Resort

3.5 out of 5
Norman Manley Boulevard Negril Westmoreland
Free Cancellation
Reserve now, pay when you stay
16.3 mi from city center
$139 nightly
The price is $156 total per night
$156 total
Oct 29 - Oct 30
Total with taxes and fees
When you stay at CocoLaPalm Seaside Resort in Negril, you'll be on the beach, a 1-minute drive from Seven Mile Beach and 6 minutes from Negril Cliffs.
Pool
Hot Tub
Samsara Cliff Resort

Samsara Cliff Resort

3.5 out of 5
West End Road Negril Westmoreland
Free Cancellation
Reserve now, pay when you stay
17.96 mi from city center
$143 nightly
The price is $159 total per night
$159 total
Oct 28 - Oct 29
Total with taxes and fees
With a stay at Samsara Cliff Resort in Negril (West End), you'll be a 1-minute drive from Negril Cliffs and 7 minutes from Seven Mile Beach.
Pool
Spa
Travellers Beach Resort

Travellers Beach Resort

3.5 out of 5
Norman Manley Boulevard Negril Westmoreland
Free Cancellation
Reserve now, pay when you stay
16.44 mi from city center
$131 nightly
The price is $147 total per night
$147 total
Nov 25 - Nov 26
Total with taxes and fees
When you stay at Travellers Beach Resort in Negril, you'll be in a shopping district, within a 5-minute drive of Seven Mile Beach and Negril Cliffs.
Pool
Parking included
Don't see what you're looking for?
See all available properties in Westmoreland
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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.

^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.