
Middlesex County Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Middlesex County Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.

Ocho Rios Villa at The Palms
Save 100% on your flight
Price was $2,699, price is now $1,469 per person
$1,469
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Montego Bay (MBJ)
Book a stay at this family-friendly villa in St. Ann's Bay. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Dunn's River Falls and Mystic Mountain are located nearby.
All staff were professional, courteous and friendly. They all went out of their way to grant your requests. The ambience is very nice. The electrical outlets on the patio didn't always work. Had to be creative in getting plugs to stay in. They also need to upgrade from 110v to 220v. Just kidding, but they should have something for travelers from Europe. Internet service was pretty good. Everyone in my group were pleased and would return. The tour setup for us by the manager was fun!!!! Good people, fantastic accommodations. Recommended...
Reviewed on May 8, 2019

Hotel Riu Palace Aquarelle - All Inclusive
Falmouth Historic Town Centre
Save 100% on your flight
Price was $4,451, price is now $2,343 per person
$2,343
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Montego Bay (MBJ)
Book a stay at this beach hotel in Falmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Water Square and Martha Brae River are located nearby.

Ocean Eden Bay - Adults Only - All inclusive
Save 100% on your flight
Price was $3,442, price is now $1,815 per person
$1,815
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Montego Bay (MBJ)
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the restaurant in our reviews. Popular attractions Burwood Beach and Blue Waters Beach Club are located nearby.
This trip was the best birthday ever! The staff was amazing and acknowledged my birthday along with a few others who shared the same birthday. Thank you for making my day special!
Reviewed on Nov 3, 2026

Hotel Riu Montego Bay - Adults Only - All Inclusive
Save 100% on your flight
Price was $3,413, price is now $1,924 per person
$1,924
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Montego Bay (MBJ)
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Doctor's Cave Beach and Rose Hall Great House are located nearby.
I went for my birthday. Ive stayed in several JA hotels and this one was just ok. Im 39 and I will say its definitely a scene for the younger crowd but i blend with everyone. One of the things i didnt like is that the pool closes at 6 sharp and music cuts off at 5 sharp. Food was average and there was NO oxtail for those oxtail lovers. I checked in on my bday and my friends requested for the hotel to decorate my room upon arrival. My friend said she spoke with staff several times and they did it a day late. The staff in charge of the pool towels refused to give me a towel because I didnt have the card even though I explained to them that I dropped off the towel when they closed and never received a card towel in return. He suggested that go to the front desk which I wasnt gonna do because I was already at the pool and it was too damn hot. Besides him all.the other staff were pretty cool. The walking is a lot if ur in a building far away. Rooms were basic but clean. Elevator is old so I always took the steps because one time the doors wouldnt close. Its definitely a 1 time visit for me. If ur not looking for luxury or anything special and just want to party then this is def the hotel for it
Reviewed on Nov 2, 2026

Hotel Riu Ocho Rios - All Inclusive
Save 100% on your flight
Price was $3,574, price is now $2,108 per person
$2,108
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Montego Bay (MBJ)
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Dunn's River Falls and Turtle Beach are located nearby.
Comfortable
Reviewed on Nov 2, 2026

Princess Grand Jamaica Resort - All Inclusive
Save 100% on your flight
Price was $4,031, price is now $2,411 per person
$2,411
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Montego Bay (MBJ)
Book a stay at this luxury resort in Green Island. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Half Moon Beach and Samuel's Bay National Marine Park are located nearby.
Good food, clean environment, nice staff
Reviewed on Nov 2, 2026
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See all available trips from Columbus to Middlesex County
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Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only- Renovated 2026
Salt Coppers Runaway Bay Saint Ann
39.99 km from city center
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Cardiff Hall Beach and ...

Couples Tower Isle All Inclusive
Tower Isle Tower Isle Saint Mary
36.95 km from city center
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Turtle Beach and ...

The Garden Hotel Mandeville
4 Hotel St Mandeville Manchester Parish
33.29 km from city center
Book a stay at this business-friendly B&B in Mandeville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Reliance Centre and Mandeville ...

Jewel Paradise Cove Adult Beach Resort & Spa – All Inclusive
Paradise Cove Drive Runaway Bay Saint Ann
39.64 km from city center
Book a stay at this beach resort in Runaway Bay. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...

Bahia Principe Explore Jamaica - Hyatt Inclusive Collection - All Inclusive - Totally Refurbished in 2026
Salt Coppers Villa Runaway Bay Saint Ann
39.96 km from city center
Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Cardiff Hall Beach and ...

Sea Shell Palms
Pompano Bay, Tower Isle Tower Isle
37.06 km from city center
Book a stay at this business-friendly hotel in Tower Isle. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...

The Cardiff Hotel & Spa
8 Riketts Ave. Runaway Bay Saint Ann
38.66 km from city center
Book a stay at this luxury resort in Runaway Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...

Franklyn D. Resort & Spa
201 Runaway Bay Runaway Bay Saint Ann
39.51 km from city center
Book a stay at this spa hotel in Runaway Bay. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...

GoldenEye
Oracabessa Oracabessa St. Mary
42.03 km from city center
Book a stay at this spa hotel in Oracabessa. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...

Golf View Hotel
5 1/2 Caledonia Road Mandeville Manchester
33.59 km from city center
Book a stay at this spa hotel in Mandeville. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...

Serenity Cove Resorts
87 Mammee Bay Rd Ocho Rios St. Ann Parish
33.74 km from city center
Stay at this resort in Ocho Rios. Enjoy free WiFi, free parking, and 2 bars/lounges. Popular attractions Dunn's River Falls and Turtle Beach are located ...

Tiamo Beach Resort and Spa
Pear Tree Bottom, Runaway Bay St. Ann
40.17 km from city center
Book a stay at this beach hotel in Runaway Bay. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cardiff Hall Beach and Ocean View Beach ...

Villa Sonate
18 MarySunley Crescent Runaway Bay Saint Ann
38.5 km from city center
Book a stay at this beach guesthouse in Runaway Bay. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Ocean View Beach and Flavours ...
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See all available properties in Middlesex County
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Nov 9 - Thu, Nov 12
JFK
John F. Kennedy Intl.
MBJ
Sir Donald Sangster Intl.
$358 Roundtrip, found 19 hours ago
$358
Roundtrip
found 19 hours ago

Sat, Nov 14 - Tue, Nov 24
ATL
Hartsfield-Jackson Atlanta Intl.
MBJ
Sir Donald Sangster Intl.
$370 Roundtrip, found 5 days ago
$370
Roundtrip
found 5 days ago

Mon, Nov 30 - Thu, Dec 17
JFK
John F. Kennedy Intl.
MBJ
Sir Donald Sangster Intl.
$384 Roundtrip, found 19 hours ago
$384
Roundtrip
found 19 hours ago

Wed, Feb 24 - Mon, Mar 1
FLL
Fort Lauderdale - Hollywood Intl.
MBJ
Sir Donald Sangster Intl.
$401 Roundtrip, found 3 days ago
$401
Roundtrip
found 3 days ago

Tue, Dec 1 - Thu, Dec 10
JFK
John F. Kennedy Intl.
MBJ
Sir Donald Sangster Intl.
$403 Roundtrip, found 4 days ago
$403
Roundtrip
found 4 days ago

