Woodlands holiday rentals

We found 39 holiday rentals — enter your dates for availability
Discover a selection of 5 villas and other holiday rentals in Woodlands that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the best amenities for hanging out with the people that matter most, which might include parking and a fireplace. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
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Why visit Woodlands

  • Pristine beaches: Enjoy the serene coastline with unspoilt sandy shores perfect for relaxation and seaside strolls.
  • Breathtaking lookouts: Marvel at the panoramic vistas from coastal trails, capturing the essence of tropical beauty.
  • Volcanic landscapes: Explore intriguing volcanic features that add a unique geological charm to the area.
  • Local cultural immersion: Experience the vibrant local traditions and welcoming atmosphere of the community.
  • Outdoor adventures: Engage in various activities that blend beach leisure with exciting explorations.

Popular types of accommodation in Woodlands

Discover Woodlands, Olveston, Saint Peter Parish, Montserrat, a charming city offering a variety of holiday rentals. Enjoy your stay in one of our villas, apartments or private holiday homes, each providing comfort and convenience. Explore local attractions, landmarks and authentic experiences unique to Woodlands, while enjoying affordable and select olveston accommodation options that cater to your holiday needs.

  • Villas: The most sought-after option, offering spacious, upscale retreats perfect for families or groups.
  • Apartments: A stylish alternative, ideal for travellers seeking modern comforts and convenient locations.
  • Private Holiday Homes: Charming standalone dwellings providing a cosy, independent stay in a peaceful setting.**

Top attractions in and around Woodlands

Woodlands, Olveston, Saint Peter Parish, Montserrat, is a delightful destination perfect for outdoor enthusiasts seeking adventure and stunning scenery. Visitors can enjoy the beautiful beaches, breathtaking lookouts, and explore the intriguing volcanic landscapes. A visit to St. Peter is also recommended for those looking to immerse themselves in local culture. This charming locale offers a unique blend of relaxation and excitement for all types of travellers.

  • Woodlands Beach: A picturesque stretch of sand perfect for relaxation, swimming, and sunbathing, offering serene beach vibes and beautiful views of the Caribbean Sea.
  • Little Bay: Located a short distance away, this beach features calm waters ideal for snorkelling and enjoying a tranquil day by the sea, surrounded by lush scenery.
  • Rendezvous Beach: A charming beach, perfect for unwinding and soaking up the sun, known for its inviting atmosphere and stunning coastal views.

Things to do recommended for couples

For a romantic getaway in Woodlands, indulge in a candlelit dinner at a seaside restaurant, followed by a moonlit stroll along the beach. Experience the local culture with a couples' dance class or enjoy a relaxing couple's massage at a nearby spa, creating cherished memories together.

Things to do recommended for families

Families visiting Woodlands in Montserrat can explore the beautiful beaches, enjoy snorkelling in crystal-clear waters, and embark on guided nature walks to discover local wildlife. Don't miss the chance to taste authentic Caribbean cuisine at family-friendly restaurants in the area.

Things to do recommended for groups

Groups visiting Woodlands can enjoy thrilling hikes through lush landscapes, partake in vibrant community festivals, and savour traditional Montserratian cuisine at local eateries. Additionally, a guided tour of the island’s historical sites offers a rich cultural experience that fosters camaraderie among travellers.

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

What do I need to keep in mind when booking a vacation in Woodlands

If you’re travelling with a group, family, pets, or seeking extended stays, it’s important to apply the right filters according to your priorities. Here are some helpful booking tips for using Stayz.

  • Traveling to Woodlands with a group: Think about how many bedrooms you'll require, along with amenities like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Stayz.
  • Traveling to Woodlands with young kids: Traveling with young children can present its own set of challenges. It is essential to prioritise their comfort and safety, ensuring access to age-appropriate facilities, such as a private swimming pool. Additionally, it is advisable to consider the closeness of family-friendly attractions.
  • Taking your pets with you to Woodlands: For many, a family holiday is not complete without the presence of their four-legged companion. If you identify with this, then have a look at Stayz properties that welcome pets. The majority of these pet-friendly properties offer feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Woodlands: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right destination. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in Woodlands

Woodlands in Saint Peter Parish offers a serene tropical retreat with captivating outdoor adventures and stunning scenery. Visitors can explore the charming village's pristine beach, enjoy leisurely walks along coastal trails, and immerse themselves in the local culture of Saint Peter. This ideal destination is perfect for those seeking a blend of beach relaxation and adventure in a picturesque setting.

  • Salem: Salem is a charming village located a mere 966m from Woodlands. This picturesque spot is perfect for outdoor enthusiasts seeking adventure and stunning scenery. Visitors can explore local landmarks such as breathtaking lookouts, the intriguing volcano, and the inviting beach. The combination of natural beauty and accessible activities makes Salem an ideal destination for those wanting to immerse themselves in Montserrat’s lush landscape.
  • Old Towne: Situated 1km from Woodlands, Old Towne is a vibrant city that draws travellers for its outdoor adventures and captivating beach experiences. Here, you can enjoy the sun and surf at the beach, hike to stunning volcanic views, and take in the spectacular lookouts that showcase the island's unique geography. Old Towne offers a delightful blend of leisure and exploration, making it a great stop for anyone visiting Montserrat.
  • Olveston: As the city where Woodlands is located, Olveston is a hub for adventure seekers and those in search of romantic experiences. Explore the nearby beach, marvel at the lookout points, and discover the majestic volcano that defines this stunning area. Olveston’s charm lies in its vibrant community and the myriad outdoor activities available, making it an excellent base for your Montserrat holiday.

Best time to go to Woodlands

If you're planning a trip to Woodlands, it's a good idea to check both the weather and property rates. The warmest month is September. Peak season runs from January to March, while off-peak times, like September to November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January78.1°F (25.6°C)No Rain (Dry)Mostly SunnyHighAverage
February77.7°F (25.4°C)No Rain (Dry)Mostly SunnyHighAverage
March77.7°F (25.4°C)No Rain (Dry)Mostly SunnyHighAverage
April78.6°F (25.9°C)No Rain (Dry)Mostly SunnyAverageAverage
May80.2°F (26.8°C)Light RainMostly SunnyAverageSlightly Low
June81.3°F (27.4°C)No Rain (Dry)Mostly SunnyAverageSlightly High
July81.7°F (27.6°C)Light RainMostly SunnyAverageSlightly High
August82.2°F (27.9°C)Light RainMostly SunnyAverageSlightly Low
September82.6°F (28.1°C)Light RainMostly SunnyLowSlightly Low
October82.0°F (27.8°C)Light RainMostly SunnyLowSlightly High
November80.8°F (27.1°C)Light RainMostly SunnyLowAverage
December79.3°F (26.3°C)Light RainMostly SunnyAverageAverage

Booking with Stayz is simple

Are you hoping to save on your next holiday? It may be beneficial to remain flexible with your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Stayz property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board provides a convenient platform for you to plan new adventures, manage your existing arrangements, or review your bookings. Your saved or reserved properties are neatly categorised into Potential, Upcoming, or Current Trips. To discover the features of Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Choose a holiday rental for your Woodlands getaway

Learn about the unique charm of Woodlands with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Exploring the natural features in Woodlands

Whether you're looking for fun outdoor activities or just want to take in the scenery, Woodlands is a great place to get out in nature. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Woodlands Beach (0.4 mi / 0.6 km)
  • Lime Kiln Beach (0.8 mi / 1.2 km)
  • Montserrat Volcano Observatory (0.9 mi / 1.5 km)
  • Foxes Bay Beach (2.4 mi / 3.9 km)
  • Little Bay (3.2 mi / 5.2 km)
  • Rendezvous Beach (3.7 mi / 6 km)

Transport to and around Woodlands

Fly into Plymouth (MNI-Gerald's Field), the closest airport, located 3.1 mi (5.1 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Woodlands?
Based on our data, villas are the most in-demand property type in Woodlands. But of course, everyone's idea of an epic stay isn't going to be the same. Stayz has holiday homes with every shape, size and budget in mind, so you're sure to discover your ideal fit.
How much does it cost to rent a holiday home in Woodlands?
A range of factors can determine how much you pay for a holiday home in Woodlands, like the length of stay, type of property and season. However, all of our holiday homes have something in common — unbeatable value. Simply add your travel dates to find your dream escape.
How much does it cost to rent a beach house in Woodlands?
The average price for a holiday home near the beach in Woodlands depends on when you're visiting the area and the type and size of property you're searching for. Find prices quickly and easily on Stayz by entering the dates you'll be travelling. Then use the handy filters to pick the number of bedrooms and amenities that you prefer, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday homes in Woodlands?
Pack up a suitcase for your canine companion because Woodlands has eight properties that welcome pets with open arms. Let your furriest friend join in on the family trip at one of our pet-friendly holiday homes on Stayz. Simply enter your travel dates then check our "Pets allowed" filter box.
Can I rent a house with a pool in Woodlands?
Check the "pool" box in our handy filter tool and take your pick of eight houses with private pools in Woodlands on Stayz. Morning soak, afternoon splash or midnight swim? How you spend your leisure time is up to you when your Stayz holiday property comes with a swimming pool.
What are popular home amenities in Woodlands?
When it comes to home amenities that guests look for in Woodlands, a barbecue grill, nearby museums and a swimming pool rank the highest. With Stayz holiday homes, you'll enjoy choices to fit your style and taste, whether you're taking a trip with your partner, your family or even pets.
Are there large group holiday homes in Woodlands?
Woodlands has two holiday homes that can accommodate 10 or more people. These properties come with all the space you need to enjoy good times with friends and family.
Are there holiday homes in Woodlands that welcome kids?
Woodlands has eight family-friendly holiday homes to pick from. And booking a stay that welcomes kiddos is super easy with Stayz's "Properties good for families" filter. Besides having the entire place to yourselves, you'll enjoy access to amenities and perks like bunk beds, full kitchens and yards.
What are the top attractions for families in Woodlands?
Woodlands Beach will keep the kiddos happy during your Woodlands break. This family-friendly attraction is located within easy reach of the centre.
Can I find two-bedroom holiday homes in Woodlands?
Gather your besties and relax in total privacy and comfort in one of the two two-bedroom holiday properties Woodlands has to offer.
Are there holiday homes with WiFi in Woodlands?
Take your pick of four holiday homes with WiFi in Woodlands. If you want to disconnect from the world on your trip, but still need to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Woodlands?
Woodlands has three holiday homes where you'll be able to relax and recharge in air-conditioned comfort. To book a property on Stayz that comes with this perk, choose your travel dates and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Woodlands?
The minimum required age is generally 16, 18 or 21. It can change from property to property on Stayz, so check the rules of your preferred Woodlands holiday home before booking your stay.
How long can I rent a holiday home in Woodlands for?
How long you can rent a holiday home in Woodlands differs according to the property. Just enter your preferred travel dates to look at a list of options offering extended stays. With plenty of amenities such as kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get somewhere perfect to call your home away from home in Woodlands.