Cheap Vacations in Portland

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Portland vacations

Price found within the past 48 hours. Click for updated prices.
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $820, price is now $726 per person
$726
per person
Mar 6 - Mar 9
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
The Emrald of the North

The Emrald of the North

3.5 out of 5
Price was $1,696, price is now $1,018 per person
$1,018
per person
Feb 20 - Feb 24
found 4 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Ocho Rios (OCJ)
Ocho Rios Skyview Guest Apartment

Ocho Rios Skyview Guest Apartment

3.5 out of 5
Price was $2,208, price is now $1,383 per person
$1,383
per person
Feb 20 - Feb 25
just found
Roundtrip non-stop flight included
Austin (AUS) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

3 out of 5
Save 100% on your flight
Price was $10,009, price is now $7,665 per person
$7,665
per person
Mar 1 - Mar 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Panoramic Cliffside Luxe Villa

Panoramic Cliffside Luxe Villa

2 out of 5
Save 100% on your flight
Price was $6,549, price is now $5,581 per person
$5,581
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,313, price is now $1,130 per person
$1,130
per person
Feb 20 - Feb 24
found 5 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $3,653, price is now $3,234 per person
$3,234
per person
Feb 22 - Mar 1
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Ocho Rios Beach Resort at ChrisAnn

Ocho Rios Beach Resort at ChrisAnn

3 out of 5
Price was $1,566, price is now $1,387 per person
$1,387
per person
Feb 26 - Mar 2
found 14 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Couples Tower Isle All Inclusive

Couples Tower Isle All Inclusive

4.5 out of 5
Price was $2,051, price is now $1,838 per person
$1,838
per person
Feb 19 - Feb 24
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Ocho Rios (OCJ)
Sea Palms Holidays

Sea Palms Holidays

2 out of 5
Price was $1,426, price is now $1,295 per person
$1,295
per person
Feb 27 - Mar 5
found 19 hours ago
Roundtrip flight included
New York (NYC) to Ocho Rios (OCJ)

3-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $820, price is now $726 per person
$726
per person
Mar 6 - Mar 9
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Save 100% on your flight
Price was $1,559, price is now $1,136 per person
$1,136
per person
Mar 5 - Mar 8
found 9 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Ocho Rios Skyview Guest Apartment

Ocho Rios Skyview Guest Apartment

3.5 out of 5
Price was $1,726, price is now $1,279 per person
$1,279
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $985, price is now $812 per person
$812
per person
Mar 6 - Mar 9
just found
Roundtrip non-stop flight included
Charlotte (CLT) to Ocho Rios (OCJ)
Coastal Escape in Riviera Tower Isle Beach Nearby

Coastal Escape in Riviera Tower Isle Beach Nearby

2 out of 5
Price was $882, price is now $810 per person
$810
per person
Feb 27 - Mar 2
found 4 hours ago
Roundtrip flight included
New York (NYC) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,143, price is now $1,059 per person
$1,059
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ocho Rios (OCJ)
Couples Tower Isle All Inclusive

Couples Tower Isle All Inclusive

4.5 out of 5
Price was $1,572, price is now $1,460 per person
$1,460
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ocho Rios (OCJ)
Sea Shell Palms

Sea Shell Palms

2.5 out of 5
Price was $855, price is now $808 per person
$808
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ocho Rios (OCJ)
El Castilito

El Castilito

2.5 out of 5
Price was $1,318, price is now $1,256 per person
$1,256
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Ocho Rios (OCJ)
The Dream Nest At Csompo Silver Manor

The Dream Nest At Csompo Silver Manor

3 out of 5
Price was $861, price is now $822 per person
$822
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ocho Rios (OCJ)

4-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $921, price is now $791 per person
$791
per person
Mar 5 - Mar 9
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
The Emrald of the North

The Emrald of the North

3.5 out of 5
Price was $1,696, price is now $1,018 per person
$1,018
per person
Feb 20 - Feb 24
found 4 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Ocho Rios (OCJ)
Ocho Rios Skyview Guest Apartment

Ocho Rios Skyview Guest Apartment

3.5 out of 5
Price was $2,076, price is now $1,514 per person
$1,514
per person
Feb 18 - Feb 22
found 5 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Panoramic Cliffside Luxe Villa

Panoramic Cliffside Luxe Villa

2 out of 5
Save 100% on your flight
Price was $6,549, price is now $5,581 per person
$5,581
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,313, price is now $1,130 per person
$1,130
per person
Feb 20 - Feb 24
found 5 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Ocho Rios (OCJ)
Ocho Rios Beach Resort at ChrisAnn

Ocho Rios Beach Resort at ChrisAnn

3 out of 5
Price was $1,566, price is now $1,387 per person
$1,387
per person
Feb 26 - Mar 2
found 14 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,248, price is now $1,117 per person
$1,117
per person
Mar 5 - Mar 9
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $4,646, price is now $4,181 per person
$4,181
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Couples Tower Isle All Inclusive

Couples Tower Isle All Inclusive

4.5 out of 5
Price was $1,699, price is now $1,531 per person
$1,531
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Ocho Rios (OCJ)
Morgans cliff

Morgans cliff

3.5 out of 5
Price was $904, price is now $822 per person
$822
per person
Mar 11 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
The Dream Nest At Csompo Silver Manor

The Dream Nest At Csompo Silver Manor

3 out of 5
Price was $918, price is now $844 per person
$844
per person
Feb 18 - Feb 22
found 7 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ocho Rios (OCJ)
Leisure Duplex At Csompo Silver Manor

Leisure Duplex At Csompo Silver Manor

2 out of 5
Price was $925, price is now $856 per person
$856
per person
Feb 18 - Feb 22
found 7 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ocho Rios (OCJ)

5-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Sea Shell Palms

Sea Shell Palms

2.5 out of 5
Price was $824, price is now $724 per person
$724
per person
Mar 8 - Mar 13
found 16 hours ago
Roundtrip flight included
Charlotte (CLT) to Ocho Rios (OCJ)
The Emrald of the North

The Emrald of the North

3.5 out of 5
Price was $1,965, price is now $1,047 per person
$1,047
per person
Feb 20 - Feb 25
just found
Roundtrip non-stop flight included
Austin (AUS) to Ocho Rios (OCJ)
Ocho Rios Skyview Guest Apartment

Ocho Rios Skyview Guest Apartment

3.5 out of 5
Price was $2,208, price is now $1,383 per person
$1,383
per person
Feb 20 - Feb 25
just found
Roundtrip non-stop flight included
Austin (AUS) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Save 100% on your flight
Price was $2,596, price is now $1,888 per person
$1,888
per person
Mar 8 - Mar 13
found 16 hours ago
Roundtrip flight included
Charlotte (CLT) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,532, price is now $1,283 per person
$1,283
per person
Feb 21 - Feb 26
found 17 hours ago
Roundtrip flight included
Charlotte (CLT) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $1,081, price is now $923 per person
$923
per person
Mar 4 - Mar 9
found 12 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,329, price is now $1,164 per person
$1,164
per person
Mar 8 - Mar 13
found 16 hours ago
Roundtrip flight included
Charlotte (CLT) to Ocho Rios (OCJ)
Morgans cliff

Morgans cliff

3.5 out of 5
Price was $900, price is now $798 per person
$798
per person
Feb 22 - Feb 27
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Couples Tower Isle All Inclusive

Couples Tower Isle All Inclusive

4.5 out of 5
Price was $2,051, price is now $1,838 per person
$1,838
per person
Feb 19 - Feb 24
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Ocho Rios (OCJ)
Coastal Escape in Tower Isle BeachNearby

Coastal Escape in Tower Isle BeachNearby

3 out of 5
Price was $1,362, price is now $1,226 per person
$1,226
per person
Mar 12 - Mar 17
found 6 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Seapalms

Seapalms

3 out of 5
Price was $1,056, price is now $955 per person
$955
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
The Dream Nest At Csompo Silver Manor

The Dream Nest At Csompo Silver Manor

3 out of 5
Price was $947, price is now $858 per person
$858
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)

6-7 night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Teal Horizon OceanfrontCaribbean Escape

Teal Horizon OceanfrontCaribbean Escape

2 out of 5
Price was $1,170, price is now $996 per person
$996
per person
Mar 2 - Mar 9
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Price was $2,695, price is now $2,050 per person
$2,050
per person
Feb 20 - Feb 26
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

3 out of 5
Save 100% on your flight
Price was $10,009, price is now $7,665 per person
$7,665
per person
Mar 1 - Mar 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Save 100% on your flight
Price was $7,890, price is now $6,206 per person
$6,206
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,263, price is now $1,045 per person
$1,045
per person
Feb 20 - Feb 26
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,285, price is now $1,093 per person
$1,093
per person
Feb 20 - Feb 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Coastal Escape in Tower Isle BeachNearby

Coastal Escape in Tower Isle BeachNearby

3 out of 5
Price was $1,417, price is now $1,206 per person
$1,206
per person
Feb 22 - Mar 1
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Sea Shell Palms

Sea Shell Palms

2.5 out of 5
Price was $1,347, price is now $1,166 per person
$1,166
per person
Mar 7 - Mar 14
found 13 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ocho Rios (OCJ)
Morgans cliff

Morgans cliff

3.5 out of 5
Price was $1,230, price is now $1,087 per person
$1,087
per person
Mar 6 - Mar 13
found 9 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ocho Rios (OCJ)
Seapalms

Seapalms

3 out of 5
Price was $1,533, price is now $1,357 per person
$1,357
per person
Mar 7 - Mar 14
found 13 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $3,653, price is now $3,234 per person
$3,234
per person
Feb 22 - Mar 1
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)

Top places to visit in Portland

Winnifred Beach which includes general coastal views as well as a small group of people
FlightsFlightsHotelsHotels

Port Antonio

Port Antonio

Flight deals to Portland

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

Mon, Feb 2 - Mon, Feb 16
FLL
Fort Lauderdale
KIN
Kingston
$275 Roundtrip, found 3 days ago
$275
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Mon, Feb 2 from Fort Lauderdale to Kingston, returning Mon, Feb 16, priced at $275 found 3 days ago
Thu, Jan 29 - Thu, Feb 5
YYZ
Toronto
KIN
Kingston
$307 Roundtrip, found 13 hours ago
$307
Roundtrip
found 13 hours ago
Select Flair Airlines flight, departing Thu, Jan 29 from Toronto to Kingston, returning Thu, Feb 5, priced at $307 found 13 hours ago
Thu, Feb 19 - Sat, Mar 7
MIA
Miami
KIN
Kingston
$309 Roundtrip, found 22 hours ago
$309
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Thu, Feb 19 from Miami to Kingston, returning Sat, Mar 7, priced at $309 found 22 hours ago

Top rated hotels for your Portland vacation

Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig Long Bay Portland
Free Cancellation
11.75 mi from city center
Get rates
With a stay at Sea Cliff Resort in Long Bay, you'll be 2.1 mi (3.3 km) from Long Bay Beach and 7.3 mi (11.7 km) from Boston Bay Beach.
Pool
Free WiFi
Jamaica Palace Hotel

Jamaica Palace Hotel

3.5 out of 5
Williamsfield Port Antonio Portland
Free Cancellation
Reserve now, pay when you stay
1.85 mi from city center
$184 nightly
The price is $204 total per night
$204 total
Jan 19 - Jan 20
Total with taxes and fees
Located in Port Antonio, Jamaica Palace Hotel is by the ocean, a 1-minute drive from Trident Castle and 7 minutes from Rio Grande.
Geejam

Geejam

4.5 out of 5
San San, Port Antonio Port Antonio Portland
2.48 mi from city center
$490 nightly
The price is $535 total per night
$535 total
Jan 19 - Jan 20
Total with taxes and fees
Located in Port Antonio, Geejam is a 3-minute drive from Trident Castle and 9 minutes from Rio Grande.
Pool
Spa
Don't see what you're looking for?
See all available properties in Portland
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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.