Cheap Vacations in Portland

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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 $726, price is now $583 per person
$583
per person
Mar 9 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Ocho Rios (OCJ)
The Emrald of the North

The Emrald of the North

3.5 out of 5
Price was $1,796, price is now $1,146 per person
$1,146
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $1,736, price is now $1,139 per person
$1,139
per person
Feb 26 - Mar 2
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 $2,237, price is now $1,659 per person
$1,659
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $5,909, price is now $4,568 per person
$4,568
per person
Feb 26 - Mar 2
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 $4,531, price is now $3,627 per person
$3,627
per person
Feb 26 - Mar 2
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 $1,214, price is now $1,033 per person
$1,033
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa in Tower Isle

Luxury Oceanfront Villa in Tower Isle

2 out of 5
Save 100% on your flight
Price was $6,700, price is now $5,768 per person
$5,768
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,036, price is now $896 per person
$896
per person
Feb 22 - Feb 27
found 16 hours ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $1,067, price is now $924 per person
$924
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 $437, price is now $371 per person
$371
per person
Feb 20 - Feb 23
found 10 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Ocho Rios (OCJ)
The Emrald of the North

The Emrald of the North

3.5 out of 5
Price was $1,320, price is now $868 per person
$868
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Ocho Rios (OCJ)
Ocho Rios Beach Resort at ChrisAnn

Ocho Rios Beach Resort at ChrisAnn

3 out of 5
Price was $1,087, price is now $1,049 per person
$1,049
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Ocho Rios (OCJ)
Ocho Rios Skyview Guest Apartment

Ocho Rios Skyview Guest Apartment

3.5 out of 5
Price was $1,477, price is now $1,023 per person
$1,023
per person
Feb 16 - Feb 19
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 $731, price is now $540 per person
$540
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Price was $1,648, price is now $1,399 per person
$1,399
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $887, price is now $767 per person
$767
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $1,793, price is now $1,553 per person
$1,553
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip 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 $1,286, price is now $1,177 per person
$1,177
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Ocho Rios (OCJ)
Sea Palms Holidays

Sea Palms Holidays

2 out of 5
Price was $1,059, price is now $972 per person
$972
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Ocho Rios (OCJ)
Seapalms

Seapalms

3 out of 5
Price was $670, price is now $620 per person
$620
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)

4-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
GC Resort

GC Resort

3 out of 5
Price was $862, price is now $745 per person
$745
per person
Feb 21 - Feb 25
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Ocho Rios (OCJ)
Panoramic Cliffside Luxe Villa

Panoramic Cliffside Luxe Villa

2 out of 5
Save 100% on your flight
Price was $6,439, price is now $4,963 per person
$4,963
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Ocho Rios (OCJ)
The Emrald of the North

The Emrald of the North

3.5 out of 5
Price was $1,796, price is now $1,146 per person
$1,146
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $1,736, price is now $1,139 per person
$1,139
per person
Feb 26 - Mar 2
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 $2,237, price is now $1,659 per person
$1,659
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $5,909, price is now $4,568 per person
$4,568
per person
Feb 26 - Mar 2
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 $4,531, price is now $3,627 per person
$3,627
per person
Feb 26 - Mar 2
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 $1,142, price is now $932 per person
$932
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Ocho Rios (OCJ)
Ocho Rios Beach Resort at ChrisAnn

Ocho Rios Beach Resort at ChrisAnn

3 out of 5
Price was $1,214, price is now $1,033 per person
$1,033
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa in Tower Isle

Luxury Oceanfront Villa in Tower Isle

2 out of 5
Save 100% on your flight
Price was $6,700, price is now $5,768 per person
$5,768
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip 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 $1,067, price is now $924 per person
$924
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $1,234, price is now $1,097 per person
$1,097
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $533, price is now $433 per person
$433
per person
Feb 22 - Feb 27
found 16 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Price was $2,225, price is now $1,518 per person
$1,518
per person
Feb 23 - Feb 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,082, price is now $820 per person
$820
per person
Feb 22 - Feb 27
found 16 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $2,581, price is now $2,104 per person
$2,104
per person
Feb 19 - Feb 24
found 7 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,036, price is now $896 per person
$896
per person
Feb 22 - Feb 27
found 16 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Ocho Rios (OCJ)
Teal Horizon OceanfrontCaribbean Escape

Teal Horizon OceanfrontCaribbean Escape

2 out of 5
Price was $934, price is now $810 per person
$810
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip 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 $1,984, price is now $1,771 per person
$1,771
per person
Feb 22 - Feb 27
found 16 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Ocho Rios (OCJ)
Morgans cliff

Morgans cliff

3.5 out of 5
Price was $999, price is now $903 per person
$903
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Sea Palms Holidays

Sea Palms Holidays

2 out of 5
Price was $1,631, price is now $1,481 per person
$1,481
per person
Feb 19 - Feb 24
found 7 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $6,235, price is now $5,688 per person
$5,688
per person
Feb 17 - Feb 22
found 2 hours ago
Roundtrip flight included
New York (JFK) 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 $726, price is now $583 per person
$583
per person
Mar 9 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $3,137, price is now $2,154 per person
$2,154
per person
Feb 21 - Feb 28
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 $1,231, price is now $851 per person
$851
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip flight included
New York (JFK) 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 $7,648 per person
$7,648
per person
Feb 28 - Mar 7
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 2 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Seapalms

Seapalms

3 out of 5
Price was $825, price is now $684 per person
$684
per person
Mar 1 - Mar 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,355, price is now $1,126 per person
$1,126
per person
Mar 9 - Mar 16
found 2 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Coastal Escape in Tower Isle BeachNearby

Coastal Escape in Tower Isle BeachNearby

3 out of 5
Price was $1,372, price is now $1,163 per person
$1,163
per person
Feb 22 - Mar 1
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 $1,184, price is now $1,013 per person
$1,013
per person
Mar 8 - Mar 15
found 1 day ago
Roundtrip flight included
New York (JFK) 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 2 hours 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.

Sun, Jan 18 - Sun, Feb 1
FLL
Fort Lauderdale
KIN
Kingston
$272 Roundtrip, found 4 days ago
$272
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sun, Jan 18 from Fort Lauderdale to Kingston, returning Sun, Feb 1, priced at $272 found 4 days ago
Sat, Feb 7 - Tue, Feb 10
MIA
Miami
KIN
Kingston
$329 Roundtrip, found 1 day ago
$329
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Feb 7 from Miami to Kingston, returning Tue, Feb 10, priced at $329 found 1 day ago
Sun, Feb 15 - Fri, Feb 20
ATL
Atlanta
KIN
Kingston
$350 Roundtrip, found 4 days ago
$350
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sun, Feb 15 from Atlanta to Kingston, returning Fri, Feb 20, priced at $350 found 4 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
$136 nightly
The price is $149 total per night
$149 total
Jan 18 - Jan 19
Total with taxes and fees
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 18 - Jan 19
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
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 18 - Jan 19
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?
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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.