Hotels in Windward Side

Find the best Windward Side hotel for your dates, by price or preference

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Look out for Windward Side hotels with free cancellation or excellent ratings

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Prices may change – pop in your dates for the best estimate. Note that prices are based on previous traveller searches and partner prices.
Prices may change – pop in your dates for the best estimate. Note that prices are based on previous traveller searches and partner prices.
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Find a Windward Side hotel in the heart of the action

Beat the queues at the top Windward Side attractions by staying close to them.

Fast facts

Sleep easy, armed with the stuff that's good to know before you go.
Highest rated hotelEl Momo Cottages – 4.2

How to find the best hotel deals in Windward Side

Want to use the same magic that powers our award-winning flight search to find the best room rates on the internet? Here are a few tips to help you search and save in seconds.

How to find the best hotel deal in Windward Side

  • You've found the right flight. Now let that same smart search engine find you the lowest rates on Windward Side hotels. These tips will get you one step closer to packing your bags.

  • Save on your Windward Side hotel and be first in line for the best rooms when you book early. You'll also have more time to compare and choose the ideal place.

  • However, you could still come across last-minute deals. Although prices typically rise closer to your stay, some places cut rates a day or two before to fill vacant rooms, especially in low season.

  • Another secret to scoring cheaper hotels? Flexibility. If your plans aren't locked in, check prices across different dates and discover what kind of savings are on offer.

  • Search for accommodation options with free cancellation and book with peace of mind. You can amend or cancel your stay without fees if your plans change or a better deal shows up.

Where to stay in Windward Side

Central Windward Side

  • Central Windward Side is where the city comes alive. If sightseeing is a big part of your plans, stay at any of these hotels and be moments from some headline attractions.

  • If you'd like to stay nice and close to Mount Scenery Trailhead, book a room at Scout''s Place. This Windward Side hotel is around 0.32 kilometres from this sight.

  • When it comes to hotels near Mount Scenery, Queen's Garden Resort & Spa stands out from the crowd. Wheel your suitcase into this 4-star hotel in Windward Side and you'll be about 2 kilometres away.

  • Hotels near Mt. Scenery Scenic View 1 are other options to keep in mind. Saba Arawak Hotel is 0.97 kilometres or so from this sight. It's a great base for discovering the city at large.

When to go to Windward Side

  • Good weather can make all the difference. If you prefer warmer conditions, September typically delivers with temperatures that reach a high of 29ºC (84ºF).

  • Lows hit 23ºC (73ºF) in February, the coolest time of year.

  • Browse around for Windward Side hotels in January to enjoy mostly clear skies. Averaging one day of rain, it's the driest month.

  • It's rainiest in October, which gets around ten days of wet weather.

Best hotels with a pool

  • Turn up the fun factor on your trip with a pool. If you pick a city hotel, expect indoor or rooftop options. Resorts? They often go all out with expansive outdoor layouts and maybe a swim-up bar or two. Book a pool hotel in Windward Side and make waves on your next adventure.

  • Make relaxing poolside a priority at El Momo Cottages. With an outdoor swimming pool, internet access and a restaurant, this Windward Side hotel makes it easy to recharge your batteries.

  • Saba Arawak Hotel gives you plenty of reasons to bring your swimsuit and goggles. Choose this popular option and take advantage of an outdoor swimming pool, a restaurant and a bar.

Finding cheap hotels in Windward Side: FAQs

You can always cancel or amend your hotel reservation if you need to, but look out for hotels in Windward Side with free cancellation or flexible booking options if you want to protect your money. Some hotels allow you to cancel and get your money back if your plans change.

Of course - the cheapest hotel deal we found within the next seven days is $155 per night. If you need somewhere in the next 24 hours, we've found you somewhere to stay for $157 per night.
The average price of a hotel during the week is $187 per night, and the average price on weekends is $188. Overall, it looks like the cheapest day to stay in Windward Side could be Sunday.
We crunched some numbers on our calendar and found that Sunday is the cheapest day to stay in Windward Side. And the most expensive day seems to be Thursday
Get your morning laps in at Saba Arawak Hotel and El Momo Cottages.