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.
Sea Shell Palms

Sea Shell Palms

2.5 out of 5
Price was $715, price is now $653 per person
$653
per person
Apr 20 - Apr 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,248, price is now $1,001 per person
$1,001
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Ocho Rios (OCJ)
Paradisiac Euphoria Beach Access Pool 24hr Gated

Paradisiac Euphoria Beach Access Pool 24hr Gated

2 out of 5
Price was $1,571, price is now $1,323 per person
$1,323
per person
Apr 4 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Price was $1,658, price is now $1,421 per person
$1,421
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $761, price is now $657 per person
$657
per person
Apr 26 - Apr 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Coastal Escape in Riviera Tower Isle Beach Nearby

Coastal Escape in Riviera Tower Isle Beach Nearby

2 out of 5
Price was $1,282, price is now $1,119 per person
$1,119
per person
Apr 22 - Apr 26
found 8 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

3 out of 5
Save 100% on your flight
Price was $4,687, price is now $4,098 per person
$4,098
per person
Apr 21 - Apr 24
found 8 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa in Tower Isle

Luxury Oceanfront Villa in Tower Isle

2 out of 5
Save 100% on your flight
Price was $5,290, price is now $4,680 per person
$4,680
per person
Apr 21 - Apr 24
found 8 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,063, price is now $954 per person
$954
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Cozy Cove Villa in Drax Hall

Cozy Cove Villa in Drax Hall

2 out of 5
Price was $1,015, price is now $911 per person
$911
per person
Apr 10 - Apr 13
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)

3-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Seapalms

Seapalms

3 out of 5
Price was $618, price is now $557 per person
$557
per person
Apr 30 - May 3
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $854, price is now $678 per person
$678
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Save 100% on your flight
Price was $3,521, price is now $3,010 per person
$3,010
per person
Apr 30 - May 3
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Price was $1,658, price is now $1,421 per person
$1,421
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $761, price is now $657 per person
$657
per person
Apr 26 - Apr 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

3 out of 5
Save 100% on your flight
Price was $4,687, price is now $4,098 per person
$4,098
per person
Apr 21 - Apr 24
found 8 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Panoramic Cliffside Luxe Villa

Panoramic Cliffside Luxe Villa

2 out of 5
Price was $5,199, price is now $4,584 per person
$4,584
per person
Apr 4 - Apr 7
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Luxury Oceanfront Villa in Tower Isle

Luxury Oceanfront Villa in Tower Isle

2 out of 5
Save 100% on your flight
Price was $5,290, price is now $4,680 per person
$4,680
per person
Apr 21 - Apr 24
found 8 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Paradisiac Euphoria Beach Access Pool 24hr Gated

Paradisiac Euphoria Beach Access Pool 24hr Gated

2 out of 5
Price was $1,044, price is now $929 per person
$929
per person
Apr 4 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Coastal Escape Tower Isle Beach Nearby

Coastal Escape Tower Isle Beach Nearby

2.5 out of 5
Price was $936, price is now $837 per person
$837
per person
Apr 21 - Apr 24
found 8 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Cozy Cove Villa in Drax Hall

Cozy Cove Villa in Drax Hall

2 out of 5
Price was $1,015, price is now $911 per person
$911
per person
Apr 10 - Apr 13
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $779, price is now $705 per person
$705
per person
Apr 26 - Apr 29
found 20 hours ago
Roundtrip 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.
Cozy Cove Villa in Drax Hall

Cozy Cove Villa in Drax Hall

2 out of 5
Price was $1,025, price is now $890 per person
$890
per person
Apr 9 - Apr 13
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
The Emrald of the North

The Emrald of the North

3.5 out of 5
Price was $1,926, price is now $1,276 per person
$1,276
per person
Apr 16 - Apr 20
found 10 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,248, price is now $1,001 per person
$1,001
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $4,793, price is now $3,952 per person
$3,952
per person
Apr 5 - Apr 9
found 9 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Price was $2,031, price is now $1,704 per person
$1,704
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Paradisiac Euphoria Beach Access Pool 24hr Gated

Paradisiac Euphoria Beach Access Pool 24hr Gated

2 out of 5
Price was $1,104, price is now $959 per person
$959
per person
Apr 5 - Apr 9
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Ocho Rios (OCJ)
Panoramic Cliffside Luxe Villa

Panoramic Cliffside Luxe Villa

2 out of 5
Save 100% on your flight
Price was $6,584, price is now $5,725 per person
$5,725
per person
Apr 21 - Apr 25
found 8 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

3 out of 5
Save 100% on your flight
Price was $6,054, price is now $5,273 per person
$5,273
per person
Apr 21 - Apr 25
found 8 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Coastal Escape in Riviera Tower Isle Beach Nearby

Coastal Escape in Riviera Tower Isle Beach Nearby

2 out of 5
Price was $1,282, price is now $1,119 per person
$1,119
per person
Apr 22 - Apr 26
found 8 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $2,922, price is now $2,572 per person
$2,572
per person
Apr 6 - Apr 10
found 15 hours ago
Roundtrip flight included
New York (NYC) to Ocho Rios (OCJ)
Coastal Escape Tower Isle Beach Nearby

Coastal Escape Tower Isle Beach Nearby

2.5 out of 5
Price was $1,052, price is now $926 per person
$926
per person
Apr 21 - Apr 25
found 8 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa in Tower Isle

Luxury Oceanfront Villa in Tower Isle

2 out of 5
Save 100% on your flight
Price was $6,857, price is now $6,049 per person
$6,049
per person
Apr 21 - Apr 25
found 8 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)

5-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $1,014, price is now $843 per person
$843
per person
Apr 25 - Apr 30
found 1 day ago
Roundtrip 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
Price was $2,190, price is now $1,374 per person
$1,374
per person
Apr 9 - Apr 14
found 17 hours ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Panoramic Cliffside Luxe Villa

Panoramic Cliffside Luxe Villa

2 out of 5
Save 100% on your flight
Price was $9,012, price is now $6,897 per person
$6,897
per person
Apr 9 - Apr 14
found 2 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa in Tower Isle

Luxury Oceanfront Villa in Tower Isle

2 out of 5
Save 100% on your flight
Price was $9,353, price is now $7,227 per person
$7,227
per person
Apr 9 - Apr 14
found 2 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,516, price is now $1,205 per person
$1,205
per person
Apr 18 - Apr 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $6,635, price is now $5,422 per person
$5,422
per person
Apr 9 - Apr 14
found 2 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

3 out of 5
Save 100% on your flight
Price was $7,260, price is now $5,951 per person
$5,951
per person
Apr 28 - May 3
found 1 day ago
Roundtrip flight included
New York (NYC) to Ocho Rios (OCJ)
Sun-soaked Paradisiac Escape 3BR Private Beach Pool

Sun-soaked Paradisiac Escape 3BR Private Beach Pool

2 out of 5
Price was $1,559, price is now $1,286 per person
$1,286
per person
Apr 22 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Price was $2,445, price is now $2,042 per person
$2,042
per person
Apr 5 - Apr 10
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,568, price is now $1,327 per person
$1,327
per person
Apr 22 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Paradisiac Euphoria Beach Access Pool 24hr Gated

Paradisiac Euphoria Beach Access Pool 24hr Gated

2 out of 5
Price was $1,127, price is now $977 per person
$977
per person
Apr 9 - Apr 14
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Cozy Cove Villa in Drax Hall

Cozy Cove Villa in Drax Hall

2 out of 5
Price was $1,395, price is now $1,216 per person
$1,216
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)

6-7 night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Seapalms

Seapalms

3 out of 5
Price was $709, price is now $582 per person
$582
per person
Apr 26 - May 2
found 13 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,582, price is now $1,206 per person
$1,206
per person
Apr 18 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Save 100% on your flight
Price was $2,971, price is now $2,382 per person
$2,382
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Sun-soaked Paradisiac Escape 3BR Private Beach Pool

Sun-soaked Paradisiac Escape 3BR Private Beach Pool

2 out of 5
Price was $1,971, price is now $1,617 per person
$1,617
per person
Apr 8 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $2,064, price is now $1,706 per person
$1,706
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $8,351, price is now $6,980 per person
$6,980
per person
Apr 6 - Apr 12
found 20 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Paradisiac Euphoria Beach Access Pool 24hr Gated

Paradisiac Euphoria Beach Access Pool 24hr Gated

2 out of 5
Price was $1,571, price is now $1,323 per person
$1,323
per person
Apr 4 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Price was $3,557, price is now $3,009 per person
$3,009
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Ocho Rios (OCJ)
Cozy Cove Villa in Drax Hall

Cozy Cove Villa in Drax Hall

2 out of 5
Price was $1,604, price is now $1,377 per person
$1,377
per person
Apr 8 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Sea Shell Palms

Sea Shell Palms

2.5 out of 5
Price was $1,424, price is now $1,255 per person
$1,255
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Ocho Rios (OCJ)
Luxury Oceanfront Villa in Tower Isle

Luxury Oceanfront Villa in Tower Isle

2 out of 5
Save 100% on your flight
Price was $11,823, price is now $10,423 per person
$10,423
per person
Apr 11 - Apr 18
found 2 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Tuscany Sun Villa at Legacy Townhouse

Tuscany Sun Villa at Legacy Townhouse

2 out of 5
Price was $3,225, price is now $2,921 per person
$2,921
per person
Apr 8 - Apr 14
found 1 day 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, Apr 24 - Mon, Apr 27
FLL
Fort Lauderdale
KIN
Kingston
$265 Roundtrip, found 16 hours ago
$265
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Fri, Apr 24 from Fort Lauderdale to Kingston, returning Mon, Apr 27, priced at $265 found 16 hours ago
Wed, Mar 11 - Sat, Mar 14
MIA
Miami
KIN
Kingston
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Mar 11 from Miami to Kingston, returning Sat, Mar 14, priced at $299 found 1 day ago
Tue, Mar 17 - Tue, Mar 31
MCO
Orlando
KIN
Kingston
$326 Roundtrip, found 2 days ago
$326
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Mar 17 from Orlando to Kingston, returning Tue, Mar 31, priced at $326 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
Get rates
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
$169 nightly
The price is $188 total per night
$188 total
Mar 26 - Mar 27
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
$490 nightly
The price is $535 total per night
$535 total
Mar 5 - Mar 6
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
Don't see what you're looking for?
See all available properties in Portland
View all properties
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.