Cheap Vacations in Portland

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Portland vacations

Price found within the past 48 hours. Click for updated prices.
Coastal Escape in Tower Isle BeachNearby

Coastal Escape in Tower Isle BeachNearby

3 out of 5
Price was $952, price is now $879 per person
$879
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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 $7,276, price is now $5,861 per person
$5,861
per person
Jun 16 - Jun 20
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 $1,258, price is now $1,174 per person
$1,174
per person
May 28 - May 31
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 $2,120, price is now $1,987 per person
$1,987
per person
May 23 - May 26
found 23 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Tropical Beach Suite

Tropical Beach Suite

3 out of 5
Price was $1,057, price is now $1,023 per person
$1,023
per person
May 22 - May 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 $3,815, price is now $1,514 per person
$1,514
per person
May 23 - May 25
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 $3,836, price is now $1,924 per person
$1,924
per person
Jun 19 - Jun 21
found 21 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $5,607, price is now $3,048 per person
$3,048
per person
May 23 - May 25
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.
Tropical Beach Suite

Tropical Beach Suite

3 out of 5
Price was $1,057, price is now $1,023 per person
$1,023
per person
May 22 - May 25
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 $1,258, price is now $1,174 per person
$1,174
per person
May 28 - May 31
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 $2,120, price is now $1,987 per person
$1,987
per person
May 23 - May 26
found 23 hours 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 $3,815, price is now $1,514 per person
$1,514
per person
May 23 - May 25
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 $3,836, price is now $1,924 per person
$1,924
per person
Jun 19 - Jun 21
found 21 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $5,607, price is now $3,048 per person
$3,048
per person
May 23 - May 25
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 $879, price is now $704 per person
$704
per person
May 31 - Jun 4
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 $7,276, price is now $5,861 per person
$5,861
per person
Jun 16 - Jun 20
found 1 day 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 $2,177, price is now $1,850 per person
$1,850
per person
Jun 15 - Jun 19
found 23 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $4,984, price is now $4,349 per person
$4,349
per person
Jun 16 - Jun 20
found 1 day 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 $1,412, price is now $1,286 per person
$1,286
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip non-stop 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 $1,716, price is now $1,565 per person
$1,565
per person
Jun 16 - Jun 20
found 1 day 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 $952, price is now $879 per person
$879
per person
Jun 11 - Jun 15
found 1 day 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 $740, price is now $717 per person
$717
per person
Jun 6 - Jun 10
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 $844, price is now $781 per person
$781
per person
Jun 16 - Jun 21
found 1 day ago
Roundtrip non-stop 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 $1,118, price is now $977 per person
$977
per person
Jun 16 - Jun 21
found 1 day 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 $1,079, price is now $956 per person
$956
per person
Jun 6 - Jun 11
found 14 hours ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,389, price is now $1,235 per person
$1,235
per person
Jun 13 - Jun 18
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 $3,166, price is now $2,855 per person
$2,855
per person
Jun 2 - Jun 7
found 1 day 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.
The Dream Nest At Csompo Silver Manor

The Dream Nest At Csompo Silver Manor

3 out of 5
Price was $1,036, price is now $857 per person
$857
per person
May 22 - May 29
found 1 day ago
Roundtrip 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 $11,666, price is now $9,000 per person
$9,000
per person
May 22 - May 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,566, price is now $1,260 per person
$1,260
per person
May 23 - May 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $7,562, price is now $6,217 per person
$6,217
per person
May 22 - May 29
found 1 day ago
Roundtrip 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 $1,567, price is now $1,331 per person
$1,331
per person
May 22 - May 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $4,008, price is now $3,528 per person
$3,528
per person
May 22 - May 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Tropical Beach Suite

Tropical Beach Suite

3 out of 5
Price was $953, price is now $874 per person
$874
per person
Jun 1 - Jun 8
found 1 day ago
Roundtrip flight included
New York (JFK) 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 6 days ago
$327
Roundtrip
found 6 days ago
Select Flair Airlines flight, departing Fri, May 8 from Toronto to Kingston, returning Fri, May 22, priced at $327 found 6 days ago
Mon, Apr 27 - Mon, May 4
FLL
Fort Lauderdale
KIN
Kingston
$338 Roundtrip, found 5 days ago
$338
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Mon, Apr 27 from Fort Lauderdale to Kingston, returning Mon, May 4, priced at $338 found 5 days ago
Tue, Jun 9 - Mon, Jun 22
EWR
New York
KIN
Kingston
$389 Roundtrip, found 6 days ago
$389
Roundtrip
found 6 days ago
Select Arajet flight, departing Tue, Jun 9 from New York to Kingston, returning Mon, Jun 22, priced at $389 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
$136 nightly
The price is $149 total per night
$149 total
Apr 24 - Apr 25
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
$161 nightly
The price is $179 total per night
$179 total
May 23 - May 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 26 - Apr 27
Total with taxes and fees
Located in Port Antonio, Geejam is a 3-minute drive from Trident Castle and 9 minutes from Rio Grande.
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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.