Cheap Vacations in Portland

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Portland vacations

Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at Coolshade V

Ocho Rios Villa at Coolshade V

3 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
per person
Jan 22 - Jan 27
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Ocho Rios Villa at the Palms II

Ocho Rios Villa at the Palms II

3.5 out of 5
Save 100% on your flight
per person
Feb 6 - Feb 11
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
The Emrald of the North

The Emrald of the North

3.5 out of 5
Save 100% on your flight
per person
Jan 25 - Feb 1
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
Ocho Rios Villa at the Palms IV

Ocho Rios Villa at the Palms IV

3 out of 5
Save 100% on your flight
per person
Feb 6 - Feb 11
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Ocho Rios Villa at Coolshade X

Ocho Rios Villa at Coolshade X

3.5 out of 5
Save 100% on your flight
per person
Feb 10 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Ocho Rios Villa at the Palms III

Ocho Rios Villa at the Palms III

3.5 out of 5
Save 100% on your flight
per person
Feb 6 - Feb 11
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Ocho Rios Villa at the Palms V

Ocho Rios Villa at the Palms V

3 out of 5
Save 100% on your flight
per person
Jan 22 - Jan 29
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Ocho Rios Villa at Coolshade IX

Ocho Rios Villa at Coolshade IX

3.5 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
Ocho Rios Treasure Villa at Coolshade XII

Ocho Rios Treasure Villa at Coolshade XII

3.5 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)

3-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Seacrest Beach Hotel

Seacrest Beach Hotel

3 out of 5
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Sea Breeze Villa at Coolshade

Sea Breeze Villa at Coolshade

3.5 out of 5
Save 100% on your flight
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Casa Maurice Ocho Rios Villa

Casa Maurice Ocho Rios Villa

4.5 out of 5
per person
Jan 21 - Jan 24
just found
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Ocho Rios Villa at the Palms VII

Ocho Rios Villa at the Palms VII

3 out of 5
per person
Feb 13 - Feb 16
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Ocho Rios Skyview Guest Apartment

Ocho Rios Skyview Guest Apartment

3.5 out of 5
per person
Feb 14 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Top Brass Ocean View Vacation Rental

Top Brass Ocean View Vacation Rental

3 out of 5
per person
Feb 14 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
123 Drax Hall Country Club Villa

123 Drax Hall Country Club Villa

3.5 out of 5
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
The Hamilton's Nature Villa

The Hamilton's Nature Villa

3 out of 5
per person
Feb 9 - Feb 12
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Sea Shell Palms

Sea Shell Palms

2.5 out of 5
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Avant Family Villa

Avant Family Villa

3.5 out of 5
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Destiny

Destiny

3 out of 5
per person
Feb 9 - Feb 12
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
per person
Feb 9 - Feb 12
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)

4-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Sea Breeze Villa at Coolshade

Sea Breeze Villa at Coolshade

3.5 out of 5
Save 100% on your flight
per person
Jan 30 - Feb 3
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
Save 100% on your flight
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Ocho Rios Villa at the Palms II

Ocho Rios Villa at the Palms II

3.5 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
Ocho Rios Villa at Coolshade X

Ocho Rios Villa at Coolshade X

3.5 out of 5
Save 100% on your flight
per person
Feb 10 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Ocho Rios Villa at the Palms V

Ocho Rios Villa at the Palms V

3 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
Ocho Rios Villa at the Palms III

Ocho Rios Villa at the Palms III

3.5 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
Ocho Rios Villa at Coolshade IX

Ocho Rios Villa at Coolshade IX

3.5 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
Ocho Rios Villa at Coolshade IV

Ocho Rios Villa at Coolshade IV

3.5 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
Ocho Rios Treasure Villa at Coolshade XII

Ocho Rios Treasure Villa at Coolshade XII

3.5 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
Ocho Rios Villa at Coolshade V

Ocho Rios Villa at Coolshade V

3 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
Ocho Rios Villa at the Palms VII

Ocho Rios Villa at the Palms VII

3 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
Ocho Rios Villa at The Palms VI

Ocho Rios Villa at The Palms VI

3.5 out of 5
Save 100% on your flight
per person
Jan 23 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)

5-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
The Crest Rental Management

The Crest Rental Management

3 out of 5
Save 100% on your flight
per person
Jan 22 - Jan 27
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
per person
Jan 22 - Jan 27
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Ocho Rios Villa at the Palms II

Ocho Rios Villa at the Palms II

3.5 out of 5
Save 100% on your flight
per person
Feb 6 - Feb 11
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Ocho Rios Villa at the Palms IV

Ocho Rios Villa at the Palms IV

3 out of 5
Save 100% on your flight
per person
Feb 6 - Feb 11
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Ocho Rios Villa at the Palms III

Ocho Rios Villa at the Palms III

3.5 out of 5
Save 100% on your flight
per person
Feb 6 - Feb 11
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Ocho Rios Villa at Coolshade X

Ocho Rios Villa at Coolshade X

3.5 out of 5
Save 100% on your flight
per person
Feb 15 - Feb 20
found 20 hours ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Ocho Rios Villa at Coolshade IV

Ocho Rios Villa at Coolshade IV

3.5 out of 5
Save 100% on your flight
per person
Feb 15 - Feb 20
found 20 hours ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Sea Breeze Villa at Coolshade

Sea Breeze Villa at Coolshade

3.5 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Top Brass Ocean View Vacation Rental

Top Brass Ocean View Vacation Rental

3 out of 5
per person
Feb 15 - Feb 20
found 20 hours ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Avant Family Villa

Avant Family Villa

3.5 out of 5
per person
Jan 22 - Jan 27
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Imperial Topaz At Richmond

Imperial Topaz At Richmond

3.5 out of 5
per person
Jan 22 - Jan 27
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
per person
Jan 22 - Jan 27
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)

6-7 night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Casa Maurice Ocho Rios Villa

Casa Maurice Ocho Rios Villa

4.5 out of 5
Save 100% on your flight
per person
Feb 8 - Feb 15
found 23 hours ago
Roundtrip non-stop flight included
Rochester (ROC) to Ocho Rios (OCJ)
Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
Save 100% on your flight
per person
Jan 22 - Jan 29
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
The Emrald of the North

The Emrald of the North

3.5 out of 5
Save 100% on your flight
per person
Jan 25 - Feb 1
found 8 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
Ocho Rios Villa at the Palms V

Ocho Rios Villa at the Palms V

3 out of 5
Save 100% on your flight
per person
Jan 22 - Jan 29
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Ocho Rios Villa at Coolshade X

Ocho Rios Villa at Coolshade X

3.5 out of 5
Save 100% on your flight
per person
Feb 14 - Feb 20
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Top Brass Ocean View Vacation Rental

Top Brass Ocean View Vacation Rental

3 out of 5
Save 100% on your flight
per person
Feb 8 - Feb 14
found 7 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Ocho Rios Skyview Guest Apartment

Ocho Rios Skyview Guest Apartment

3.5 out of 5
Save 100% on your flight
per person
Feb 8 - Feb 14
found 7 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Avant Family Villa

Avant Family Villa

3.5 out of 5
Save 100% on your flight
per person
Feb 8 - Feb 15
found 20 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
The Palms Richmond Oasis

The Palms Richmond Oasis

3 out of 5
per person
Jan 22 - Jan 29
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury 4-Bedroom villa

Luxury 4-Bedroom villa

5 out of 5
Save 100% on your flight
per person
Feb 5 - Feb 11
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Lot 40 Draxhall

Lot 40 Draxhall

3 out of 5
per person
Feb 9 - Feb 15
found 7 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Mahoe Villa Richmond Estate

Mahoe Villa Richmond Estate

3.5 out of 5
per person
Feb 14 - Feb 20
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)

Top places to visit in Portland

Winnifred Beach which includes general coastal views as well as a small group of people
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, Jan 24 - Mon, Feb 3
FLL
Fort Lauderdale
KIN
Kingston
$241 Roundtrip, found 5 hours ago
$241
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Fri, Jan 24 from Fort Lauderdale to Kingston, returning Mon, Feb 3, priced at $241 found 5 hours ago
Mon, Feb 24 - Fri, Feb 28
YYZ
Toronto
KIN
Kingston
$290 Roundtrip, found 5 days ago
$290
Roundtrip
found 5 days ago
Select Flair Airlines flight, departing Mon, Feb 24 from Toronto to Kingston, returning Fri, Feb 28, priced at $290 found 5 days ago
Thu, Jan 9 - Fri, Jan 17
BOS
Boston
KIN
Kingston
$314 Roundtrip, found 1 day ago
$314
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Jan 9 from Boston to Kingston, returning Fri, Jan 17, priced at $314 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
11.75 mi from city center
The price is $367 per night
$367
includes taxes & fees
$337 per night
Jan 4 - Jan 5, 2025
When you stay at Sea Cliff Resort in Long Bay, you'll be near the beach, within a 5-minute drive of Jamaica Beaches and Long Bay Beach.
Jamaica Palace Hotel

Jamaica Palace Hotel

3.5 out of 5
Williamsfield, Port Antonio, Portland
Free Cancellation
1.85 mi from city center
The price is $204 per night
$204
includes taxes & fees
$184 per night
Jan 5 - Jan 6, 2025
Located in Port Antonio, Jamaica Palace Hotel is by the ocean, a 1-minute drive from Trident Castle and 7 minutes from Rio Grande.
Geejam

Geejam

4.5 out of 5
San San, Port Antonio, Port Antonio, Portland
2.48 mi from city center
The price is $535 per night
$535
includes taxes & fees
$490 per night
Jan 6 - Jan 7, 2025
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.