Middlesex Holidays from NZ$1,321

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Middlesex Holiday Deals

Price found within the past 48 hours. Click for updated prices.
237 Bratton Ave
Hotel Riu Palace Jamaica - Adults Only - All Inclusive
Deja Resort All Inclusive
Round Hill Hotel And Villas
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

Middlesex Holiday

Our pick of the best Middlesex Hotel Deals

Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
Industry Cove Green Island Hanover
The price is NZ$871 per night from 4 May to 5 May
NZ$871
4 May - 5 May
includes taxes & fees
8.8/10 Excellent! (810 reviews)
Fantastic stay. Friendly staff. Only issue was a la carte wait times. Just would have preferred an estimate of time.

Reviewed on 5 Apr 2026

Princess Grand Jamaica Resort - All Inclusive
Deja Resort All Inclusive

Deja Resort All Inclusive

3.5 out of 5
92 Gloucester Avenue Montego Bay Saint James
The price is NZ$395 per night from 6 May to 7 May
NZ$395
6 May - 7 May
includes taxes & fees
8/10 Very Good! (1,667 reviews)
3.5 ⭐ – Good stay overall Clean rooms, friendly staff, and very good food. Be aware the hotel is not directly on the beach — you need to cross the strip (staff assist), and beach chairs cost extra. Minibar could be better stocked with local beer options. Overall, we enjoyed our stay, just important ...

Reviewed on 4 Apr 2026

Deja Resort All Inclusive
Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

4 out of 5
Industry Cove Green Island Hanover
The price is NZ$1,309 per night from 20 Apr to 21 Apr
NZ$1,309
20 Apr - 21 Apr
includes taxes & fees
9.2/10 Wonderful! (579 reviews)
Enjoyed the property especially since it was Adults only!

Reviewed on 4 Apr 2026

Princess Senses The Mangrove Resort - Adults Only
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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.