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
Price was $2,324, price is now $2,071 per person
$2,071
per person
Jul 23 - Jul 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 $2,082, price is now $1,948 per person
$1,948
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
New York (JFK) 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 $2,324, price is now $2,071 per person
$2,071
per person
Jul 23 - Jul 27
found 1 day 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 $2,725, price is now $2,275 per person
$2,275
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Price was $4,213, price is now $3,868 per person
$3,868
per person
Aug 1 - Aug 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.

Mon, Jun 15 - Mon, Jun 22
YYZ
Toronto
KIN
Kingston
$341 Roundtrip, found 1 day ago
$341
Roundtrip
found 1 day ago
Select Flair Airlines flight, departing Mon, Jun 15 from Toronto to Kingston, returning Mon, Jun 22, priced at $341 found 1 day ago
Sat, Sep 12 - Mon, Sep 21
MIA
Miami
KIN
Kingston
$389 Roundtrip, found 4 days ago
$389
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Sep 12 from Miami to Kingston, returning Mon, Sep 21, priced at $389 found 4 days ago
Sun, Sep 20 - Mon, Sep 28
FLL
Fort Lauderdale
KIN
Kingston
$389 Roundtrip, found 1 day ago
$389
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Sep 20 from Fort Lauderdale to Kingston, returning Mon, Sep 28, priced at $389 found 1 day 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
Jul 1 - Jul 2
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
$165 nightly
The price is $184 total per night
$184 total
Jun 28 - Jun 29
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
Jun 14 - Jun 15
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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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.