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Holidays to Woodlands

Choose two or more items and save on your trip:

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

Top Hotel Deals

Miles Away Resort
Miles Away Resort
2.5 out of 5
Mayfield Valley View Rd, Olveston
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
Sea Song Caribbean Villa
Sea Song Caribbean Villa
3.5 out of 5
Sea Song, Olveston, Olveston
Situated near the beach, this holiday home is 0.1 mi (0.1 km) from Woodlands Beach and within 3 miles (5 km) of Montserrat Volcano Observatory and Lime Kiln ...
Sea Song Caribbean Villa
Secluded 2 Bedroom Villa With Breathtaking Views Over the Caribbean Sea
Secluded 2 Bedroom Villa With Breathtaking Views Over the Caribbean Sea
This family-friendly Olveston villa is located by the ocean, within 3 mi (5 km) of Woodlands Beach, Montserrat Volcano Observatory and Lime Kiln Beach. Little ...
4/5Very Good! (9 reviews)
Great location
"Clean and welcoming, the owner was very communicative and helpful. Will definitely be back."

Reviewed on 1 Aug 2021

Secluded 2 Bedroom Villa With Breathtaking Views Over the Caribbean Sea
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.

Frequently asked questions

Woodlands Beach Holiday

Listen to the waves crashing onto the shore and stare out over the shimmering waters on your Woodlands holiday. If you're in need of some time out, a trip to Woodlands is your ticket to rest and relaxation. We have a great range of Woodlands packages to select from. Snap up one close to Woodlands Beach, just 0.3 miles from the centre of town, and live out your holiday dreams without blowing your budget.

Plan your Woodlands 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 Woodlands. 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.