Book The Best Hotels in Cudjoe Head for 2026 from CA $261 - Fully Refundable Options

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Our top choices for Cudjoe Head hotels

Chez Mango Villas

Old Towne

Audrey

CA $261 total

includes taxes & fees

Jul 5 - Jul 6

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Top Cudjoe Head Hotel Reviews

Lucy's Sunny Villa apartments, spacious & modern, your ideal tropical retreat.

10/10 Excellent

"I really enjoyed having air conditioning and the instant hot shower was wonderful. Host was in the UK so communication was affected by the time difference. The local lady was very helpful when I needed something, though."

Oceanfront Luxury. Spectacular Sunsets and Mountain View. HHI Featured. Avalon.

10/10 Excellent

"It was a wonderful stay. We went about and had a fun time all over the island, seeing places, connecting and reconnecting with people. But coming back to the property every time was beyond beautiful and totally relaxing. The pool and the amazing view washed up my tired day and prepared me for relaxing nights. Thank you Marie for your assistance when was needed. You were great!"

Secluded 2 Bedroom Villa With Breathtaking Views Over the Caribbean Sea

8/10 Good

"Great location, close to beach, quiet and private. Nice covered veranda. Great view. Property manager, Yvette, was very helpful and available. Nice cleaning person with service included in rent."

Caribbean Villa with private pool & ocean view in the heart of Montserrat .

10/10 Excellent

"Adams Place was the best appointed VRBO of which I've had the pleasure of staying. The home is expansive with tropical gardens and has all the amenities of your own private home. Nothing is lacking. The owners and managers of the property are extremely attentive and accommodating. Our interactions were always positive and our stay was elevated because of them.Surrounding this wonderful home is the beautiful and unique island of Montserrat. Their marriage is perfect and they must be considered as one. Me and my party did not have any specific preconceptions of Montserrat; we were paralyzed by the beauty of the surroundings, the warmth of the people, and the island's singular history, both recent and more distant.If you need a reset. If you want to be remote ... just enough. This is the address.*Oh, and watching the sunrise over the ridgeline as clouds and mist pour across their apex, well that's just nuts."

Oceanfront luxury - 4 beds, AC, 3 bedrooms, king bed, WiFi, gated

10/10 Excellent

"Entering the home, you are instantly greeted with a view through the glass doors to the pool and the Caribbean Sea beyond. The family room is bright and spacious, leading either to the master bedroom and bath to the left, the two remaining bedrooms and bath to the right, or the indoor dining and kitchen area. Continuing through the well-appointed kitchen is a second access to the covered patio and large pool area.The entire home is clean and well-maintained. We did not utilize additional housekeeping services during our time here, but the option is there for you if you choose. While air conditioning is not always needed on the island due to constant trade winds, it was a welcome relief, especially during sleep, and the units worked flawlessly.The propane grill situated on the patio got heavy use during our stay and is a great way to keep added heat out of the kitchen during meals.As perfect as the home is, the patio and pool area are where it is all at! From the pool, you get 180 degrees of private Caribbean sea views looking North towards Woodland Beach and South to Old Town. An occasional passing sailboat or yacht only adds to the vibe. The large pool offered much-needed relief from the hours spent staring into the sea.We had zero issues during our 14-day stay and would not hesitate to stay at Villa Kurtena in the future and to recommend it to our family and friends. Thank you, David, for sharing your home with us."

More cheap stays in Cudjoe Head

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Davy Hill Davy Hill Saint Peter Parish

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Frequently asked questions

What is the best area to stay in Cudjoe Head?

The best area to stay in Cudjoe Head is the main village area itself, particularly around the central crossroads and the road leading towards the coast.

This area offers a concentration of local amenities and is well-connected for exploring the rest of the island. You'll find a few local shops and eateries within easy reach, and it acts as a convenient base for accessing the nearby beaches and natural attractions. The general layout is fairly spread out, with homes and guesthouses located amongst the green hillsides.

For couples seeking a peaceful retreat, staying in a guesthouse or villa just off the main road in Cudjoe Head can be ideal. You'll enjoy privacy and often stunning views of the Caribbean Sea, great for relaxing evenings. Many accommodations in this area provide private balconies or terraces where you can enjoy the natural surroundings.

Families will appreciate the convenience of being centrally located while still enjoying a relaxed environment. The proximity to local services means less travel time for essentials, and it's a good starting point for day trips to sites like the Montserrat Volcano Observatory or Rendezvous Beach, the island's only white sand beach.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Cudjoe Head.

How can I save on a Cudjoe Head hotel booking with Expedia?

Members always get our best prices. Find our best Cudjoe Head hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.

How much is the nightly rate at a Cudjoe Head hotel?

Prices for hotels in Cudjoe Head often vary, but you can find a great deal from CA $261 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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Our top choices for Cudjoe Head hotels

Chez Mango Villas

Top Cudjoe Head Hotel Reviews

Lucy's Sunny Villa apartments, spacious & modern, your ideal tropical retreat.

Chez Mango Villas

Lucy's Sunshine Villa Palm Loop, Spacious 3 Bed 2 Bathroom,

Oceanfront Luxury. Spectacular Sunsets and Mountain View. HHI Featured. Avalon.

Secluded 2 Bedroom Villa With Breathtaking Views Over the Caribbean Sea

Caribbean Villa with private pool & ocean view in the heart of Montserrat .

Oceanfront luxury - 4 beds, AC, 3 bedrooms, king bed, WiFi, gated

Luxury Spacious Villa with Aircon and Pool Table

More cheap stays in Cudjoe Head

Convenient location easy reach to main

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app

Find hotels in Cudjoe Head from CA $261

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Cudjoe Head

Check prices for these dates

Filter by

Guest rating

Star rating

Our top choices for Cudjoe Head hotels

Chez Mango Villas

Top Cudjoe Head Hotel Reviews

Lucy's Sunny Villa apartments, spacious & modern, your ideal tropical retreat.

More cheap stays in Cudjoe Head

Convenient location easy reach to main

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app