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 $2,691, price is now $2,411 per person
$2,411
per person
Oct 22 - Oct 27
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 $2,892, price is now $2,558 per person
$2,558
per person
Oct 16 - Oct 19
found 6 hours ago
Roundtrip non-stop 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 $2,434, price is now $2,279 per person
$2,279
per person
Oct 22 - Oct 26
found 21 hours ago
Roundtrip non-stop flight included
Nashville (BNA) 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 $2,691, price is now $2,411 per person
$2,411
per person
Oct 22 - Oct 27
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.

Wed, Jun 2 - Wed, Jun 9
LGA
New York
KIN
Kingston
$335 Roundtrip, found 2 days ago
$335
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Jun 2 from New York to Kingston, returning Wed, Jun 9, priced at $335 found 2 days ago
Fri, Oct 16 - Thu, Oct 29
YYZ
Toronto
KIN
Kingston
$365 Roundtrip, found 5 days ago
$365
Roundtrip
found 5 days ago
Select Flair Airlines flight, departing Fri, Oct 16 from Toronto to Kingston, returning Thu, Oct 29, priced at $365 found 5 days ago
Sun, Apr 11 - Sat, Apr 17
JFK
New York
KIN
Kingston
$381 Roundtrip, found 2 days ago
$381
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sun, Apr 11 from New York to Kingston, returning Sat, Apr 17, priced at $381 found 2 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
Sep 15 - Sep 16
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
Sep 14 - Sep 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.
Pool
Breakfast included
Match Resort Hotel

Match Resort Hotel

3 out of 5
Dolphin Bay Port Antonio
Free Cancellation
Reserve now, pay when you stay
1.39 mi from city center
$94 nightly
The price is $104 total per night
$104 total
Sep 14 - Sep 15
Total with taxes and fees
When you stay at Match Resort Hotel in Port Antonio, you'll be near the beach and within a short 3-minute drive from Trident Castle.
Pool
Parking included
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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.