Cheap Vacations in Portland

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Portland vacations

Price found within the past 48 hours. Click for updated prices.
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $751, price is now $639 per person
$639
per person
Jan 9 - Jan 11
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Ocho Rios (OCJ)
The Emrald of the North

The Emrald of the North

3.5 out of 5
Save 100% on your flight
Price was $1,472, price is now $837 per person
$837
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Top Brass Ocean View Vacation Rental

Top Brass Ocean View Vacation Rental

3 out of 5
Price was $1,600, price is now $1,069 per person
$1,069
per person
Jan 16 - Jan 21
found 1 day 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 $2,592, price is now $1,897 per person
$1,897
per person
Jan 18 - Jan 23
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 $866, price is now $713 per person
$713
per person
Jan 4 - Jan 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $4,479, price is now $3,736 per person
$3,736
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Serenity Oasis Apartment

Serenity Oasis Apartment

2 out of 5
Price was $779, price is now $656 per person
$656
per person
Jan 6 - Jan 13
found 5 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Afiba View Villa

Afiba View Villa

3.5 out of 5
Price was $1,392, price is now $1,179 per person
$1,179
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $1,322, price is now $1,136 per person
$1,136
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Casa Maria Hotel

Casa Maria Hotel

3.5 out of 5
Price was $1,111, price is now $958 per person
$958
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)

3-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 $533, price is now $465 per person
$465
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Ocho Rios (OCJ)
Lagardan Ocean View

Lagardan Ocean View

3 out of 5
Save 100% on your flight
Price was $1,363, price is now $905 per person
$905
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $822, price is now $642 per person
$642
per person
Jan 15 - Jan 18
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $866, price is now $713 per person
$713
per person
Jan 4 - Jan 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Price was $1,531, price is now $1,310 per person
$1,310
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Seapalms

Seapalms

3 out of 5
Price was $583, price is now $531 per person
$531
per person
Jan 4 - Jan 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $1,154, price is now $1,054 per person
$1,054
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Teal Horizon OceanfrontCaribbean Escape

Teal Horizon OceanfrontCaribbean Escape

2 out of 5
Price was $969, price is now $892 per person
$892
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Leisure Duplex At Csompo Silver Manor

Leisure Duplex At Csompo Silver Manor

2 out of 5
Price was $591, price is now $547 per person
$547
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Apartment E6

Apartment E6

3.5 out of 5
Price was $510, price is now $473 per person
$473
per person
Jan 15 - Jan 18
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Ocho Rios (OCJ)
Sky's Villa Resort

Sky's Villa Resort

3 out of 5
Price was $629, price is now $587 per person
$587
per person
Jan 11 - Jan 14
found 22 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
El Castilito

El Castilito

2.5 out of 5
Price was $897, price is now $845 per person
$845
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)

4-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 $653, price is now $559 per person
$559
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Ocho Rios (OCJ)
The Emrald of the North

The Emrald of the North

3.5 out of 5
Save 100% on your flight
Price was $1,472, price is now $837 per person
$837
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Ocho Rios Skyview Guest Apartment

Ocho Rios Skyview Guest Apartment

3.5 out of 5
Save 100% on your flight
Price was $1,684, price is now $1,100 per person
$1,100
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Lagardan Ocean View

Lagardan Ocean View

3 out of 5
Save 100% on your flight
Price was $1,786, price is now $1,176 per person
$1,176
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,349, price is now $1,114 per person
$1,114
per person
Jan 7 - Jan 11
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Ocho Rios (OCJ)
Casa Maria Hotel

Casa Maria Hotel

3.5 out of 5
Price was $740, price is now $612 per person
$612
per person
Jan 4 - Jan 8
found 15 hours 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 $4,479, price is now $3,736 per person
$3,736
per person
Jan 21 - Jan 25
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 $1,942, price is now $1,650 per person
$1,650
per person
Jan 14 - Jan 18
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $991, price is now $869 per person
$869
per person
Jan 29 - Feb 2
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 $933, price is now $826 per person
$826
per person
Jan 21 - Jan 25
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 $1,190, price is now $1,055 per person
$1,055
per person
Jan 4 - Jan 8
found 15 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Teal Horizon OceanfrontCaribbean Escape

Teal Horizon OceanfrontCaribbean Escape

2 out of 5
Price was $761, price is now $678 per person
$678
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $623, price is now $512 per person
$512
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Lagardan Ocean View

Lagardan Ocean View

3 out of 5
Save 100% on your flight
Price was $1,977, price is now $1,174 per person
$1,174
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Top Brass Ocean View Vacation Rental

Top Brass Ocean View Vacation Rental

3 out of 5
Price was $1,600, price is now $1,069 per person
$1,069
per person
Jan 16 - Jan 21
found 1 day 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 $2,592, price is now $1,897 per person
$1,897
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,364, price is now $1,106 per person
$1,106
per person
Jan 27 - Feb 1
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Afiba View Villa

Afiba View Villa

3.5 out of 5
Price was $1,392, price is now $1,179 per person
$1,179
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $1,190, price is now $1,020 per person
$1,020
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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 $1,322, price is now $1,136 per person
$1,136
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Casa Maria Hotel

Casa Maria Hotel

3.5 out of 5
Price was $1,111, price is now $958 per person
$958
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Teal Horizon OceanfrontCaribbean Escape

Teal Horizon OceanfrontCaribbean Escape

2 out of 5
Price was $901, price is now $791 per person
$791
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop 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 $2,859, price is now $2,557 per person
$2,557
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Apartment E6

Apartment E6

3.5 out of 5
Price was $706, price is now $643 per person
$643
per person
Jan 16 - Jan 21
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.
Sea Shell Palms

Sea Shell Palms

2.5 out of 5
Price was $753, price is now $625 per person
$625
per person
Jan 25 - Jan 31
found 21 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Ocho Rios (OCJ)
Lagardan Ocean View

Lagardan Ocean View

3 out of 5
Save 100% on your flight
Price was $2,357, price is now $1,374 per person
$1,374
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,046, price is now $719 per person
$719
per person
Jan 15 - Jan 21
found 19 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,289, price is now $971 per person
$971
per person
Jan 11 - Jan 17
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Serenity Oasis Apartment

Serenity Oasis Apartment

2 out of 5
Price was $779, price is now $656 per person
$656
per person
Jan 6 - Jan 13
found 5 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Save 100% on your flight
Price was $3,034, price is now $2,565 per person
$2,565
per person
Jan 4 - Jan 10
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Seapalms

Seapalms

3 out of 5
Price was $841, price is now $720 per person
$720
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Ocho Rios (OCJ)
Teal Horizon OceanfrontCaribbean Escape

Teal Horizon OceanfrontCaribbean Escape

2 out of 5
Price was $1,351, price is now $1,179 per person
$1,179
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $1,925, price is now $1,682 per person
$1,682
per person
Jan 4 - Jan 10
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Ocho Rios (OCJ)
Paradise Reggae Resort

Paradise Reggae Resort

3 out of 5
Price was $832, price is now $735 per person
$735
per person
Jan 6 - Jan 13
found 5 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Apartment E6

Apartment E6

3.5 out of 5
Price was $1,140, price is now $1,037 per person
$1,037
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Starlight Chalet

Starlight Chalet

3 out of 5
Price was $825, price is now $751 per person
$751
per person
Jan 6 - Jan 13
found 5 hours ago
Roundtrip non-stop 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.

Fri, Jan 23 - Mon, Jan 26
FLL
Fort Lauderdale
KIN
Kingston
$253 Roundtrip, found 7 hours ago
$253
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Fri, Jan 23 from Fort Lauderdale to Kingston, returning Mon, Jan 26, priced at $253 found 7 hours ago
Thu, Jan 22 - Fri, Jan 30
MIA
Miami
KIN
Kingston
$298 Roundtrip, found 1 day ago
$298
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Jan 22 from Miami to Kingston, returning Fri, Jan 30, priced at $298 found 1 day ago
Wed, Jan 7 - Tue, Jan 20
YYZ
Toronto
KIN
Kingston
$330 Roundtrip, found 6 days ago
$330
Roundtrip
found 6 days ago
Select WestJet flight, departing Wed, Jan 7 from Toronto to Kingston, returning Tue, Jan 20, priced at $330 found 6 days 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
Geejam

Geejam

4.5 out of 5
San San, Port Antonio Port Antonio Portland
2.48 mi from city center
$435 nightly
The price is $475 total per night
$475 total
Dec 7 - Dec 8
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
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
$147 nightly
The price is $164 total per night
$164 total
Dec 8 - Dec 9
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.
Pool
Breakfast included
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.