Cheap Vacations in Portland

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Portland vacations

Price found within the past 48 hours. Click for updated prices.
3rd Floor Condo Tower Isle 24hr Security

3rd Floor Condo Tower Isle 24hr Security

3 out of 5
Price was $1,061, price is now $975 per person
$975
per person
May 31 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $2,439, price is now $2,046 per person
$2,046
per person
Jun 6 - Jun 10
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,320, price is now $1,134 per person
$1,134
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Ocho Rios Beach Resort at ChrisAnn

Ocho Rios Beach Resort at ChrisAnn

3 out of 5
Price was $1,479, price is now $1,271 per person
$1,271
per person
May 26 - May 31
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Ocean s Edge Fully Staffed Luxury Villa

Ocean s Edge Fully Staffed Luxury Villa

2 out of 5
Price was $5,336, price is now $4,845 per person
$4,845
per person
Jun 6 - Jun 9
found 16 hours ago
Roundtrip non-stop 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
Price was $4,939, price is now $4,490 per person
$4,490
per person
Jun 6 - Jun 9
found 16 hours ago
Roundtrip non-stop 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 $1,298, price is now $1,187 per person
$1,187
per person
May 31 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $1,374, price is now $1,274 per person
$1,274
per person
May 21 - May 24
found 7 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $3,622, price is now $3,376 per person
$3,376
per person
Jun 6 - Jun 9
found 16 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Teal Horizon OceanfrontCaribbean Escape

Teal Horizon OceanfrontCaribbean Escape

3 out of 5
Price was $1,282, price is now $1,205 per person
$1,205
per person
May 21 - May 24
found 7 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)

3-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
3rd Floor Condo Tower Isle 24hr Security

3rd Floor Condo Tower Isle 24hr Security

3 out of 5
Price was $972, price is now $909 per person
$909
per person
May 25 - May 28
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,153, price is now $1,015 per person
$1,015
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Ocean s Edge Fully Staffed Luxury Villa

Ocean s Edge Fully Staffed Luxury Villa

2 out of 5
Price was $5,336, price is now $4,845 per person
$4,845
per person
Jun 6 - Jun 9
found 16 hours ago
Roundtrip non-stop 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
Price was $4,939, price is now $4,490 per person
$4,490
per person
Jun 6 - Jun 9
found 16 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
Price was $2,452, price is now $2,250 per person
$2,250
per person
Jun 5 - Jun 8
found 1 day 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 $1,142, price is now $1,057 per person
$1,057
per person
May 25 - May 28
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $1,374, price is now $1,274 per person
$1,274
per person
May 21 - May 24
found 7 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $3,622, price is now $3,376 per person
$3,376
per person
Jun 6 - Jun 9
found 16 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Teal Horizon OceanfrontCaribbean Escape

Teal Horizon OceanfrontCaribbean Escape

3 out of 5
Price was $1,282, price is now $1,205 per person
$1,205
per person
May 21 - May 24
found 7 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
The Dream Nest At Csompo Silver Manor

The Dream Nest At Csompo Silver Manor

3 out of 5
Price was $960, price is now $909 per person
$909
per person
Jun 6 - Jun 9
found 16 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Tropical Beach Suite

Tropical Beach Suite

3 out of 5
Price was $1,010, price is now $976 per person
$976
per person
May 22 - May 25
found 15 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Coastal Escape Tower Isle Beach Nearby

Coastal Escape Tower Isle Beach Nearby

2.5 out of 5
Price was $1,259, price is now $1,216 per person
$1,216
per person
Jun 6 - Jun 9
found 16 hours 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.
3rd Floor Condo Tower Isle 24hr Security

3rd Floor Condo Tower Isle 24hr Security

3 out of 5
Price was $1,061, price is now $975 per person
$975
per person
May 31 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Ocean s Edge Fully Staffed Luxury Villa

Ocean s Edge Fully Staffed Luxury Villa

2 out of 5
Save 100% on your flight
Price was $7,264, price is now $5,687 per person
$5,687
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $2,439, price is now $2,046 per person
$2,046
per person
Jun 6 - Jun 10
found 17 hours ago
Roundtrip 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 $6,497, price is now $5,465 per person
$5,465
per person
May 31 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $4,934, price is now $4,203 per person
$4,203
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,320, price is now $1,134 per person
$1,134
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Ocho Rios Beach Resort at ChrisAnn

Ocho Rios Beach Resort at ChrisAnn

3 out of 5
Price was $1,312, price is now $1,130 per person
$1,130
per person
May 28 - Jun 1
found 9 hours ago
Roundtrip 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 $1,553, price is now $1,419 per person
$1,419
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Coastal Escape in Tower Isle BeachNearby

Coastal Escape in Tower Isle BeachNearby

3 out of 5
Price was $1,298, price is now $1,187 per person
$1,187
per person
May 31 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Coastal Escape Tower Isle Beach Nearby

Coastal Escape Tower Isle Beach Nearby

2.5 out of 5
Price was $1,548, price is now $1,422 per person
$1,422
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
The Dream Nest At Csompo Silver Manor

The Dream Nest At Csompo Silver Manor

3 out of 5
Price was $1,239, price is now $1,140 per person
$1,140
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Teal Horizon OceanfrontCaribbean Escape

Teal Horizon OceanfrontCaribbean Escape

3 out of 5
Price was $1,443, price is now $1,340 per person
$1,340
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)

5-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Tropical Beach Suite

Tropical Beach Suite

3 out of 5
Price was $892, price is now $838 per person
$838
per person
May 26 - May 31
found 10 hours ago
Roundtrip 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 $8,131, price is now $6,331 per person
$6,331
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $2,660, price is now $2,207 per person
$2,207
per person
May 26 - May 31
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,287, price is now $1,069 per person
$1,069
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Ocean s Edge Fully Staffed Luxury Villa

Ocean s Edge Fully Staffed Luxury Villa

2 out of 5
Save 100% on your flight
Price was $8,815, price is now $7,348 per person
$7,348
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $5,903, price is now $4,989 per person
$4,989
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Ocho Rios Beach Resort at ChrisAnn

Ocho Rios Beach Resort at ChrisAnn

3 out of 5
Price was $1,479, price is now $1,271 per person
$1,271
per person
May 26 - May 31
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Coastal Escape Tower Isle Beach Nearby

Coastal Escape Tower Isle Beach Nearby

2.5 out of 5
Price was $1,811, price is now $1,622 per person
$1,622
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $1,666, price is now $1,499 per person
$1,499
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
The Dream Nest At Csompo Silver Manor

The Dream Nest At Csompo Silver Manor

3 out of 5
Price was $1,284, price is now $1,160 per person
$1,160
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Teal Horizon OceanfrontCaribbean Escape

Teal Horizon OceanfrontCaribbean Escape

3 out of 5
Price was $1,539, price is now $1,410 per person
$1,410
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
3rd Floor Condo Tower Isle 24hr Security

3rd Floor Condo Tower Isle 24hr Security

3 out of 5
Price was $1,326, price is now $1,216 per person
$1,216
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)

6-7 night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Tropical Beach Suite

Tropical Beach Suite

3 out of 5
Price was $962, price is now $901 per person
$901
per person
Jun 6 - Jun 13
found 14 hours ago
Roundtrip non-stop flight included
New York (LGA) 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 $10,722, price is now $8,485 per person
$8,485
per person
Jun 1 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,430, price is now $1,167 per person
$1,167
per person
May 23 - May 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $3,366, price is now $2,796 per person
$2,796
per person
Jun 6 - Jun 13
found 14 hours ago
Roundtrip non-stop flight included
New York (LGA) to Ocho Rios (OCJ)
Ocho Rios Beach Resort at ChrisAnn

Ocho Rios Beach Resort at ChrisAnn

3 out of 5
Price was $1,594, price is now $1,340 per person
$1,340
per person
Jun 10 - Jun 16
found 17 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
Ocean s Edge Fully Staffed Luxury Villa

Ocean s Edge Fully Staffed Luxury Villa

2 out of 5
Save 100% on your flight
Price was $11,649, price is now $9,908 per person
$9,908
per person
Jun 1 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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 $7,650, price is now $6,606 per person
$6,606
per person
Jun 1 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Ocho Rios (OCJ)
The Dream Nest At Csompo Silver Manor

The Dream Nest At Csompo Silver Manor

3 out of 5
Price was $1,437, price is now $1,246 per person
$1,246
per person
Jun 1 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $1,936, price is now $1,703 per person
$1,703
per person
Jun 1 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Ocho Rios (OCJ)
Coastal Escape Tower Isle Beach Nearby

Coastal Escape Tower Isle Beach Nearby

2.5 out of 5
Price was $2,134, price is now $1,892 per person
$1,892
per person
Jun 1 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Ocho Rios (OCJ)
3rd Floor Condo Tower Isle 24hr Security

3rd Floor Condo Tower Isle 24hr Security

3 out of 5
Price was $1,483, price is now $1,326 per person
$1,326
per person
Jun 1 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Ocho Rios (OCJ)
Teal Horizon OceanfrontCaribbean Escape

Teal Horizon OceanfrontCaribbean Escape

3 out of 5
Price was $1,767, price is now $1,596 per person
$1,596
per person
Jun 1 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Ocho Rios (OCJ)

Top places to visit in Portland

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, May 8 - Fri, May 22
YYZ
Toronto
KIN
Kingston
$327 Roundtrip, found 3 days ago
$327
Roundtrip
found 3 days ago
Select Flair Airlines flight, departing Fri, May 8 from Toronto to Kingston, returning Fri, May 22, priced at $327 found 3 days ago
Mon, Apr 27 - Mon, May 4
FLL
Fort Lauderdale
KIN
Kingston
$338 Roundtrip, found 3 days ago
$338
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Mon, Apr 27 from Fort Lauderdale to Kingston, returning Mon, May 4, priced at $338 found 3 days ago
Tue, Jun 9 - Mon, Jun 22
EWR
New York
KIN
Kingston
$389 Roundtrip, found 4 days ago
$389
Roundtrip
found 4 days ago
Select Arajet flight, departing Tue, Jun 9 from New York to Kingston, returning Mon, Jun 22, priced at $389 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
Apr 22 - Apr 23
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
Apr 23 - Apr 24
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
$435 nightly
The price is $475 total per night
$475 total
Apr 22 - Apr 23
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.