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.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • Little Bay (3.2 mi / 5.2 km)
  • Soufriere Hills Volcano (4.6 mi / 7.4 km)
  • Katy Hill (1.7 mi / 2.7 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 best area to stay in Woodlands when booking a holiday rental?
When considering a holiday rental in Woodlands, Saint Peter Parish, Montserrat, a popular area to stay is near the coast, where you'll find a lovely blend of tranquillity and stunning views. This coastal area is known for its beautiful beaches and inviting atmosphere, making it great for relaxation and exploration.A standout feature of this region is the nearby Little Bay, a charming beach that offers opportunities for swimming, sunbathing, and enjoying the local scenery. Additionally, the Montserrat Volcano Observatory, not far from Woodlands, provides fascinating insights into the island's volcanic activity, making it an intriguing visit for those interested in natural wonders.In terms of properties, there are a variety of holiday rentals available in the Woodlands area, suiting different preferences and budgets. Whether you're seeking a cosy cottage or a more spacious villa, you're likely to find something that suits your needs here.
What are the top attractions in Woodlands?
In Woodlands, Saint Peter Parish, Montserrat, visitors can explore the beautiful natural landscapes and rich cultural heritage of the island. One of the main attractions is the Montserrat Volcano Observatory, where travellers can learn about the island's volcanic history and enjoy panoramic views of the surrounding area.Additionally, the nearby Woodlands Beach offers a tranquil setting for relaxation and swimming, with its soft sands and crystal-clear waters. For those interested in hiking, the scenic trails of the Centre Hills provide opportunities to witness Montserrat's lush flora and fauna, along with breathtaking vistas of the coastline.The charming local village atmosphere in Woodlands allows visitors to experience the warm hospitality of the island, with traditional eateries and shops showcasing Montserrat's unique culture.
Are all fees included in the Woodlands holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Woodlands holiday homes with parking?
Stayz offers a wide selection of holiday homes in Woodlands with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Woodlands holiday homes?
You can find great discounts on holiday homes in Woodlands on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Woodlands holiday home booking on Stayz?
To find Woodlands holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Woodlands?
A long-stay holiday home in Woodlands is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Woodlands holiday home?
Book your Woodlands holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Woodlands?
Prices for holiday homes in Woodlands vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Woodlands to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.