Cheap Vacations in Portland

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Portland vacations

Price found within the past 48 hours. Click for updated prices.
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $2,439, price is now $2,179 per person
$2,179
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip 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.
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $1,853, price is now $1,561 per person
$1,561
per person
Sep 25 - Sep 28
found 23 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)

4-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $2,439, price is now $2,179 per person
$2,179
per person
Sep 2 - Sep 6
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.
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $2,829, price is now $2,333 per person
$2,333
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)

Top places to visit in Portland

A beach with clear turquoise water, a rocky coastline, and a small structure on a cliff.
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.

Sat, Sep 26 - Mon, Oct 5
YYZ
Toronto
KIN
Kingston
$350 Roundtrip, found 1 day ago
$350
Roundtrip
found 1 day ago
Select Arajet flight, departing Sat, Sep 26 from Toronto to Kingston, returning Mon, Oct 5, priced at $350 found 1 day ago
Tue, Oct 27 - Wed, Nov 4
LGA
New York
KIN
Kingston
$367 Roundtrip, found 1 day ago
$367
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 27 from New York to Kingston, returning Wed, Nov 4, priced at $367 found 1 day ago
Tue, Nov 10 - Tue, Nov 17
JFK
New York
KIN
Kingston
$367 Roundtrip, found 4 hours ago
$367
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Tue, Nov 10 from New York to Kingston, returning Tue, Nov 17, priced at $367 found 4 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
$136 nightly
The price is $149 total per night
$149 total
Aug 9 - Aug 10
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.
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
$165 nightly
The price is $184 total per night
$184 total
Aug 14 - Aug 15
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.
LF Jungle Retreat

LF Jungle Retreat

3 out of 5
Lots 32-40, Willamsfield Port Antonio
Free Cancellation
Reserve now, pay when you stay
2.15 mi from city center
$97 nightly
The price is $108 total per night
$108 total
Aug 6 - Aug 7
Total with taxes and fees
With a stay at LF Jungle Retreat in Port Antonio, you'll be within a 5-minute drive of Trident Castle and San San Beach.
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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.