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Holidays to Cudjoe Head

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Accommodation, flights, car rentals, things to do and more - for your holiday in Cudjoe Head choose Expedia! Find everything you need to organise your trip to Cudjoe Head in one place. Enter your dates in the search bar above or scroll to our top deals below!

Top Hotel Deals

Most Amazing View in Town
Most Amazing View in Town
The price is £102 per night from 15 Apr to 16 Apr

Located in the heart of Cudjoe Head, this villa is within 3 miles (5 km) of Little Bay, Woodlands Beach and Rendezvous Beach. Montserrat Volcano Observatory ...

4/5Very Good! (2 reviews)

"Amazing views;very helpful manager Luckily the weather was very good and warm because no hot water in the house."…"

Reviewed on 17 Feb 2020

Most Amazing View in Town
Miles Away Resort
Miles Away Resort
2.5 out of 5
Mayfield Valley View Rd, Olveston
The price is £113 per night from 15 Apr to 16 Apr

Situated by the sea, this hotel is within 3 mi (5 km) of Montserrat Volcano Observatory, Lime Kiln Beach and Woodlands Beach. Foxes Bay Beach and Little Bay ...

4.8/5Exceptional! (20 reviews)

"Had a great time. The owner was very friendly professional and just bobbly / if I ever travel back to Montserrat I will stay here again. Beautiful property. Amazing location. The view amazing. ❤️❤️❤️❤️"…"

Reviewed on 29 Mar 2020

Miles Away Resort
Spacious 1 Bedroom Apartment to Rent in Montserrat West Indies
Spacious 1 Bedroom Apartment to Rent in Montserrat West Indies

Situated in St. John's, this apartment building is 1.7 mi (2.8 km) from Little Bay and 2.7 mi (4.4 km) from Rendezvous Beach. Woodlands Beach and Montserrat ...

5/5Exceptional! (1 review)
Just wonderful

"I have to say that since I have been visiting Montserrat, this apartment is the best have I stayed in.The view is beautiful from all windows, the neighbors very friendly and our privacy respected. It was like a home from home! Everything we needed for a comfortable stay was there including WiFi and ..."…"

Reviewed on 13 Aug 2018

Spacious 1 Bedroom Apartment to Rent in Montserrat West Indies
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.

Plan your Cudjoe Head holiday with Expedia

  • Book your 2021 holiday package deals now! Buy your accommodation, flight or car together and get extra savings on your next trip!
  • We have selected for you amazing deals on incredible hotels in Cudjoe Head. Have a look simply by using the search bar above.
  • Most hotels come with free cancellation, because we believe that flexibility matters now more than ever!

For more information, visit our COVID-19 information page
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*Some hotels require you to cancel at least 24-48 hours before check-in.

Frequently asked questions

If I'm not able to travel, can I cancel my Cudjoe Head holiday package?
You can change or cancel your booking, but whether you’ll incur a fee depends on what and when you booked. If you’ve locked in a Cudjoe Head holiday package in the last 24 hours, you may be able to cancel or change your itinerary for free. If it’s been more than 24 hours, your airline, hotel or car rental company may impose a fee. Have a look at our Customer Service Portal for more information.
When is the best time of year to visit Cudjoe Head?
There’s no right or wrong time to holiday in Cudjoe Head. But if you’d like to save big on your getaway, consider the month of . Airfares and hotel prices tend to be at their highest in . Cudjoe Head can be a busy place in , so if you want to dodge the masses, pack your bags for .
How far in advance should I book my Cudjoe Head holiday?
Reserving your flights early with Expedia means one less thing to worry about. Most air carriers advertise prices up to a year in advance. This is typically the cheapest time to book. If circumstances have left you booking late, discount prices to Cudjoe Head are still known to appear a few weeks before departure.
What should I know before booking a Cudjoe Head travel package?
When you book your flights, hotels and car rentals together, you’ll land awesome discounts. Whether you’re organising a wilderness getaway in a cabin or want to stay in a ritzy city hotel, Expedia can help make it happen.
Does Expedia offer Book Now, Pay Later Cudjoe Head holiday packages?
If you like to spread the cost of your activities and hotel over multiple payments, Expedia is here to help. Paying the full amount for your journey upfront isn’t always the best way to pay for your holiday, so we’ve teamed up with online lender Affirm to give you financial freedom. Book Now, Pay Later and reduce the stress of saving to travel.