Middle Region Holidays from £789

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected
Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was £1,592, price is now £789 per person
£789
per person
14 Jul - 19 Jul
found 10 hours ago
Return direct flight included
Port of Spain (POS) to Philipsburg (SXM)
8.8/10 Excellent! (1,665 reviews)
The marina room we had was perfect. It was a mini apartment. Property was easy walking distance to groceries stores and restaurants surrounding property. We also lived the onsite property guarded parking. Would definently stay and recommend this property to anyone.

Reviewed on 1 May 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was £3,332, price is now £1,997 per person
£1,997
per person
2 Jul - 9 Jul
found 1 day ago
Return direct flight included
London (LHR) to Philipsburg (SXM)
9.2/10 Wonderful! (1,386 reviews)
We really enjoyed our visit, the villa was very nice, very clean, although the bathroom was a little dated. The staff were very helpful and attentive, always with a smile. We would recommend staying there to anyone, the onsite food was excellent and plenty of pool/beach options. Lots of within walking distance options for dining and recreation.

Reviewed on 1 May 2026

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was £2,605, price is now £2,002 per person
£2,002
per person
21 Jul - 28 Jul
found 1 day ago
Return direct flight included
London (LHR) to Philipsburg (SXM)
9.4/10 Exceptional! (687 reviews)
The American Breakfast was very good!

Reviewed on 29 Apr 2026

Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was £2,524, price is now £1,999 per person
£1,999
per person
2 Jul - 9 Jul
found 1 day ago
Return direct flight included
London (LHR) to Philipsburg (SXM)
9.6/10 Exceptional! (50 reviews)
My stay in Sint Maarten was nothing short of amazing. The apartment was clean, spacious, and beautifully maintained, making it feel like a home away from home. From the moment I arrived, everything was set up perfectly, and the attention to detail really stood out. The location was ideal—close to the beach, restaurants, and local attractions, yet still peaceful enough to relax and unwind. Waking up to the island breeze and scenic views every day was a highlight of the trip. The amenities were exactly as described, and everything worked smoothly. Whether it was lounging inside or stepping out to explore, the apartment provided the perfect balance of comfort and convenience. Overall, this was a great experience, and I would definitely stay here again. I highly recommend it to anyone looking for a relaxing and enjoyable stay in Sint Maarten.

Reviewed on 22 Apr 2026

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was £2,459, price is now £1,977 per person
£1,977
per person
2 Jul - 9 Jul
found 1 day ago
Return direct flight included
London (LHR) to Philipsburg (SXM)
8.2/10 Very Good! (1,007 reviews)
Very clean property, rooms were so clean and very nice. Staff were friendly, great beach front , clean pools.

Reviewed on 1 May 2026

Top hotels in Middle Region

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
The price is £288 per night from 5 May to 6 May
£288
5 May - 6 May
includes taxes & fees
9/10 Wonderful! (2,109 reviews)
The doors need to close safety hazard

Reviewed on 1 May 2026

The Morgan Resort Spa Village
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
1 Rhine Road Lowlands
The price is £300 per night from 19 May to 20 May
£300
19 May - 20 May
includes taxes & fees
8/10 Very Good! (2,929 reviews)
Pleasant staff

Reviewed on 1 May 2026

Sonesta Maho Beach All Inclusive Resort Casino & Spa
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
The price is £211 per night from 25 May to 26 May
£211
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (1,684 reviews)
The marina room we had was perfect. It was a mini apartment. Property was easy walking distance to groceries stores and restaurants surrounding property. We also lived the onsite property guarded parking. Would definently stay and recommend this property to anyone.

Reviewed on 1 May 2026

Simpson Bay Resort, Marina & Spa
See all 3,593 properties in Middle Region
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Middle Region travel package cost?
We make it simple to see the world, with Middle Region packages starting from as little as £789. You'll have the flexibility to combine your favourite hotels, airlines and car rental. For the ultimate escape, why not add a few tours and experiences to your itinerary?
If I'm not able to travel, can I cancel my Middle Region travel package?
Whether it's your flight or hotel, you can cancel or change it. Locked in your Middle Region travel package in the last 24 hours? You may be able to make changes at no cost. For bookings made more than 24 hours ago, you may incur a charge from your airline, hotel or car rental company. For more information, check out our Customer Service Portal. We'll help you each step of the way.
How do I get a cheap travel package to Middle Region?
Search for flights that fit your busy schedule, add a hotel room to your booking and watch the savings rack up with a Middle Region travel package. It's as easy as that! From hotels and flights to rental cars and tours, Expedia makes travelling cheaply a cinch. And with more than 550 partner airlines and 1,000,000 hotels all over the world to choose from, you won't be short of choice.
Does Expedia offer Book Now, Pay Later Middle Region holidays?
Your bank balance shouldn't prevent you from going on holiday, so Expedia has come up with a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a terrific getaway without eating away at your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's monthly instalment plans. If paying small amounts each month sounds right for you, choose this option during the checkout process.
  • Pay in instalments holidays: If you'd prefer to pay off your getaway across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you see an amazing deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you secure your getaway.

What are the top hotels in Middle Region?
Whether you'll be staying for one night or longer in Middle Region, you'll get a solid night's sleep at Stunning Beachfront Condo In Cupecoy Walk To Auc. This option is popular with plenty of travellers.
How far in advance should I book my Middle Region holiday?
It depends on the airline, but you can normally browse through international airfares on Expedia up to a year in advance. While it's generally recommended to book ahead of time, lucky travellers will sometimes nab a cheaper ticket only weeks before departure dates.
What does an Expedia Middle Region travel package include?
With Expedia, you can choose any combination of flights, car rentals and hotels to build your ideal Middle Region travel package. Once you've made your booking, you can add on fun stuff like tours and activities. Don't forget, the more you bundle, the more you stand to save!
What should I know before booking a Middle Region travel package?
Our prices are always low. However, you'll enjoy even more bargains if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and a terrific range of choice.
Can I choose my airline with a Middle Region Expedia travel package?
You can, and with more than 550 airlines to choose from all over the world, you have loads of choice. Have a look through the available options and find out which airline best suits your budget and needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.