Montserrat Vacations & Trips from $4,432

Book a Hotel + Flight or Car together to unlock savings

Photo by Pav B

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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

    Plan, book, and manage your trip all in one place

Your Montserrat Vacation

Book a vacation package to Montserrat and make travel planning a breeze. With the logistics arranged before you depart, you can focus on enjoying every second in this lively destination. You'll have a long list of must-sees during your trip to Montserrat. One top city you'll want to spend some time in is Plymouth. Expedia has hotels, flights and all your other travel needs to help you curate your own tailored Montserrat vacation today.

The Latest Montserrat Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Chez Mango Villas

Chez Mango Villas

3.5 out of 5
Price was $4,560, price is now $4,432 per person
$4,432
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Plymouth (MNI)
7.2/10 Good! (26 reviews)
I like the bathroom spacious a mirror over the sink would’ve completed. We were there for a wedding so a workable iron would be nice there was an iron there but with English voltage and would need a transformer. I also wished there was a kettle as I need a cuppa to start my day otherwise it was delightful.

Reviewed on Aug 14, 2025

Best Places to Vacation in Montserrat

1. Experience Old Towne with a travel package

Old Towne in Saint Peter Parish, Montserrat offers a serene and picturesque atmosphere for outdoor vacation experiences. With its stunning beaches and beautiful landscapes, it is the perfect destination for beach lovers. The local vibe is laid-back and welcoming, allowing travelers to relax and unwind. Whether you want to swim in the crystal-clear waters, sunbathe on the golden sands, or explore the nearby hiking trails, Old Towne has something for everyone. The local community is friendly and hospitable, ensuring a memorable and enjoyable vacation experience. So come and immerse yourself in the natural beauty and tranquility of Old Towne.

  • Travelers tend to stay 3 days in Old Towne

2. Discover Olveston with our vacation deals

Olveston in Saint Peter Parish, Montserrat offers a unique outdoor vacation experience. With its stunning beaches and beautiful natural surroundings, it is the perfect destination for beach lovers. Explore the crystal-clear waters, go snorkeling or diving to witness the vibrant marine life, or simply relax on the sandy shores. The local atmosphere is laid-back and welcoming, allowing you to immerse yourself in the tranquil surroundings. Whether you want to sunbathe, swim, or indulge in water sports, Olveston has it all. Escape the hustle and bustle of everyday life and enjoy a peaceful and rejuvenating vacation in this idyllic beach town.

  • Travelers tend to stay 6 days in Olveston

3. Escape to Plymouth with a vacation package

Plymouth, Montserrat offers a unique and captivating outdoor vacation experience. The local atmosphere is filled with natural beauty and adventure. Explore the stunning natural parks, where you can hike through lush forests and discover breathtaking viewpoints. The beaches in Plymouth are a paradise for sunbathing, swimming, and water sports. Immerse yourself in the serene coastal atmosphere and enjoy the warm Caribbean waters. With its geographic affinities, Plymouth provides the perfect setting for an unforgettable outdoor vacation. Take in the stunning landscapes, indulge in thrilling activities, and create memories that will last a lifetime.

4. Book your ideal St. Peter's with a vacation package

St. Peter's in Montserrat offers a stunning outdoor vacation experience. The local atmosphere is serene and inviting, with breathtaking natural beauty at every turn. The parish is home to lush green mountains, pristine beaches, and crystal-clear waters, perfect for hiking, snorkeling, and diving. Explore the Blackwood Allen Trail, a picturesque hiking trail that winds through the rainforest, or relax on the golden sands of Rendezvous Bay. Immerse yourself in the local culture by visiting the Montserrat Cultural Centre, where you can learn about the island's history and enjoy live performances. St. Peter's promises an unforgettable outdoor adventure.

  • Travelers tend to stay 6 days in St. Peter's

6. Plan your dream getaway to Davy Hill

Gerald's in Saint Peter Parish, Montserrat offers a tranquil and breathtaking atmosphere for an outdoor vacation. Surrounded by lush greenery and stunning landscapes, visitors can immerse themselves in the natural beauty of the area. Explore the nearby hiking trails that lead to breathtaking viewpoints, or relax on the pristine beaches and enjoy the crystal-clear waters. Gerald's also provides opportunities for adventurous activities such as snorkeling, diving, and fishing. With its serene atmosphere and abundance of outdoor activities, Gerald's is the perfect destination for nature lovers seeking a peaceful and rejuvenating vacation.

  • Travelers tend to stay 2 days in Davy Hill

5. Create memories in St. John's with a vacation package

Davy Hill in Saint Peter Parish, Montserrat offers a tranquil and picturesque atmosphere for a beach vacation. With its stunning coastline, pristine white sand beaches, and crystal-clear turquoise waters, it is the perfect destination for relaxation and rejuvenation. The local atmosphere is laid-back and friendly, with a focus on enjoying the natural beauty of the surroundings. Visitors can indulge in various water activities such as swimming, snorkeling, and diving, or simply unwind on the beach and soak up the sun. The local cuisine offers a delicious blend of Caribbean flavors, adding to the overall experience of this idyllic beach getaway.

  • Travelers tend to stay 18 days in St. John's

Things to do in Montserrat

Montserrat offers a perfect blend of outdoor adventures and relaxation, making it ideal for beach vacations and scenic getaways. Popular activities include exploring local resorts, visiting the vibrant public market, and enjoying a round of golf. Don't miss out on top trips to Plymouth and other stunning areas, ensuring a memorable experience on this beautiful Caribbean island.

Shopping

In Montserrat, visit the Little Bay shopping area for unique local crafts and souvenirs. Check out the Montserrat Marketplace for fresh produce and handmade goods. You'll find charming boutiques in Plymouth offering artwork and jewelry, perfect for gifts to remember your trip.

Recreation

At the Montserrat Wellness Centre, indulge in rejuvenating massages and holistic therapies surrounded by lush landscapes. Explore the vibrant hiking trails of the Soufrière Hills, and unwind at the serene beaches where you can practice yoga or meditation, all while soaking in the island's tranquil atmosphere.

Adventure

Embark on the Blackwood Allen Trail for a scenic hike through lush landscapes, or tackle the Cot Trail to experience breathtaking views. The Duberry-Cassava Trail offers another thrilling adventure, showcasing Montserrat's stunning outdoor beauty and vibrant scenery that will leave you in awe.

Nightlife

In Montserrat, enjoy a vibrant nightlife with reggae and calypso music at local bars like the Olveston House and the famous beach bar at Little Bay. Look for live events at the Montserrat Cultural Centre, where you can dance and socialize with friendly locals under the stars.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Montserrat

Montserrat offers a perfect blend of outdoor adventures, stunning beaches, and breathtaking scenery for your vacation. Explore popular attractions like the Montserrat Monastery, scenic lookouts, and volcanic landscapes. Whether you're seeking a luxury travel experience or a relaxing beach getaway, Montserrat has something for everyone. Don't forget to check out the local hotels for a comfortable stay while you enjoy this beautiful Caribbean destination.

  • Montserrat Volcano Observatory: Experience breathtaking views from this lookout, where you can witness the power of nature firsthand. The observatory offers outdoor adventures and romantic settings, perfect for soaking in the stunning landscapes of Montserrat.
  • Woodlands Beach: Relax at this beautiful beach, known for its soft sands and inviting waters. With a laid-back beach vibe, Woodlands Beach is ideal for sunbathing, swimming, and enjoying the tranquil atmosphere of the Caribbean.
  • Soufriere Hills Volcano: Explore the majestic Soufriere Hills Volcano, where outdoor enthusiasts can hike and admire the dramatic scenery. This active volcano offers an adventurous experience, showcasing the raw beauty of Montserrat's natural environment.

Tips to save on your trip to Montserrat

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Find the Best Montserrat Vacation Packages

Montserrat Essential Information

Language
English
Currency
East Caribbean dollars
Closest Airport
Plymouth (MNI-Geralds Field)
Top Sights
Woodlands Beach, Lime Kiln Beach and Montserrat Volcano Observatory

Montserrat Hotel Deals

Chez Mango Villas

Chez Mango Villas

3.5 out of 5
Old Towne Old Towne
7.2/10 Good! (27 reviews)
I like the bathroom spacious a mirror over the sink would’ve completed. We were there for a wedding so a workable iron would be nice there was an iron there but with English voltage and would need a transformer. I also wished there was a kettle as I need a cuppa to start my day otherwise it was ...

Reviewed on Aug 14, 2025

Get rates
Chez Mango Villas
Cozy apartment in lovely Olveston with AC, WiFi. Close to Salem and Old town.

Cozy apartment in lovely Olveston with AC, WiFi. Close to Salem and Old town.

Olveston Saint Peter Parish
$366 nightly
The price is $366 total per night from Jan 13 to Jan 14
$366 total
Jan 13 - Jan 14
Total with taxes and fees
10/10 Exceptional! (1 review)
McAuthurs Ville
The overall experience was wonderful, the accommodation offered us everything that we wanted. The situation of the Ville was perferct for our needs, and within easy reach of the whole island.We would definitely want to stay there again.

Reviewed on May 18, 2025

Cozy apartment in lovely Olveston with AC, WiFi. Close to Salem and Old town.
Oceanfront luxury - 4 beds, AC, 3 bedrooms, king bed, WiFi, gated

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

Woodlands Saint Peter Parish
9.8/10 Exceptional! (14 reviews)
Everything about this property is superb. Stunning location, very clean, all amenities you could want and a beautiful island to explore.

Reviewed on Jan 2, 2026

Get rates
Oceanfront luxury - 4 beds, AC, 3 bedrooms, king bed, WiFi, gated
See all 40 properties in Montserrat
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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Montserrat vacation package cost?
From just $4,432, you can custom build your Montserrat package the way you want. Simply combine flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Montserrat?
Lock in flights that suit your schedule, add a hotel to your booking and watch the savings rack up with a Montserrat vacation package. It's as easy as that! From flights and hotels to activities and rental cars, Expedia makes traveling cheap and easy. And with more than 550 air carriers and 1,000,000 hotels around the globe to select from, you won't be short of choice.
What are the top hotels in Montserrat?
Chez Mango Villas and Luxurious Penthouse with Breathtaking Views know how to make their guests feel welcome in Old Towne. If your itinerary also includes Olveston, take a look at Rosedale Villa and Oceanfront luxury - 4 beds, AC, 3 bedrooms, king bed, WiFi, gated. Both are popular with travelers.
How far in advance should I book my Montserrat vacation?
Savvy travelers always book early. Air carriers typically advertise flights around a year prior to departure, and this is your chance to land some rock-bottom prices. Just been told you need to take all your vacation days next week? No problem! Expedia are never short of fantastic deals to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia Montserrat travel package include?
Expedia has all you need to book your Montserrat trip, but what your package looks like is totally up to you. Choose from any combination of flights, hotels and rental cars. Chasing some activities to fill in your time? Once you've made your booking, you can add them too. No matter your budget or style, there's a package to suit your needs.
What should I know before booking a Montserrat travel package?
Locking in all the parts of your trip together is an excellent way to save. Combine car rentals, airfares and hotels into a convenient little package. But you're not restricted to hotels. Expedia offers all sorts of properties, including vacation rentals such as beachside villas and spacious residences. Your choices are almost endless!
Can I choose my airline with a Montserrat Expedia vacation package?
Yes — that's the beauty of an Expedia package. You're in charge! We have more than 550 airline partners all over the world, so you have lots of choice when arranging your Montserrat adventure.
Does Expedia offer Book Now, Pay Later Montserrat vacation packages?
Thanks to the combined experience of Expedia and online lender Affirm, you can split the price of your package booking over several installments. For financial freedom, have a look at our Book Now, Pay Later option and structure a payment plan that suits your circumstances.
If I'm not able to travel, can I cancel my Montserrat vacation package?
Whether it's your hotel, flight or rental car, you can cancel and rebook it. Booked your Montserrat vacation package in the last 24 hours? You may be able to make changes or cancellations for free. For bookings older than that, you may be charged a fee by your airline, hotel or car rental company. For more information, take a look at our Customer Service Portal. We're here to help you each step of the way.

Discover the most popular places to visit in Montserrat

Lime Kiln Beach

Why not spend a carefree afternoon at Lime Kiln Beach during your travels in Salem?

Lime Kiln Beach

Little Bay

Why not spend a carefree afternoon at Little Bay during your travels in Gerald's?

Little Bay

Woodlands Beach

Why not spend a carefree afternoon at Woodlands Beach during your travels in Woodlands?

Woodlands Beach
Explore a world of travel with Expedia

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.