Cheap Vacations in Portland

Choose two or more items and save on your trip:

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
Save 100% on your flight
Price was $3,081, price is now $2,686 per person
$2,686
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,865, price is now $1,763 per person
$1,763
per person
Dec 1 - Dec 4
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $2,265, price is now $2,043 per person
$2,043
per person
Nov 27 - Dec 1
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $3,031, price is now $2,710 per person
$2,710
per person
Dec 3 - Dec 8
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Ocho Rios (OCJ)

6-7 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
Save 100% on your flight
Price was $3,081, price is now $2,686 per person
$2,686
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Thu, Nov 12 - Thu, Dec 24
YYZ
Toronto
KIN
Kingston
$415 Roundtrip, found 8 hours ago
$415
Roundtrip
found 8 hours ago
Select Flair Airlines flight, departing Thu, Nov 12 from Toronto to Kingston, returning Thu, Dec 24, priced at $415 found 8 hours ago
Tue, Dec 1 - Sat, Dec 5
EWR
New York
KIN
Kingston
$441 Roundtrip, found 20 hours ago
$441
Roundtrip
found 20 hours ago
Select Arajet flight, departing Tue, Dec 1 from New York to Kingston, returning Sat, Dec 5, priced at $441 found 20 hours ago
Sun, Dec 6 - Fri, Dec 11
JFK
New York
KIN
Kingston
$491 Roundtrip, found 6 days ago
$491
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, Dec 6 from New York to Kingston, returning Fri, Dec 11, priced at $491 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
11.75 mi from city center
$199 nightly
The price is $217 total per night
$217 total
Nov 3 - Nov 4
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
$138 nightly
The price is $153 total per night
$153 total
Oct 29 - Oct 30
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
$425 nightly
The price is $475 total per night
$475 total
Oct 29 - Oct 30
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
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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.