Brewster holiday lettings

We found 92 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Brewster to find one that's perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll have the amenities that you expect and more, which might include a fireplace and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

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Why people love visiting friendly Brewster

Enjoy the entertainment and other features of Brewster. Revered for its shopping, restaurants and wildlife, this city is both welcoming and relaxing. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Brewster

Are you searching for attractions to visit in the city? Venture out of your holiday home and experience everything that Brewster has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Centennial Golf Club (2.9 mi / 4.7 km)
  • Richter Park Golf Course (5.2 mi / 8.3 km)
  • Putnam County Golf Course (7.4 mi / 11.9 km)
  • Thunder Ridge Ski Resort (7.9 mi / 12.7 km)
  • Beekman Golf Course (15.8 mi / 25.5 km)
  • Fishkill Golf Course (16.6 mi / 26.7 km)

Exploring the natural features in Brewster

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Brewster is a great place to spend some time outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Ives Concert Park (6.1 mi / 9.8 km)
  • Lake Mahopac (6.5 mi / 10.5 km)
  • Tarrywile Park and Mansion (8.6 mi / 13.9 km)
  • Candlewood Lake (10.9 mi / 17.6 km)
  • Oscawana Lake (12 mi / 19.4 km)
  • Boscobel House and Gardens (16.7 mi / 26.8 km)

Transport to and around Brewster

The nearest airport is in Danbury, CT (DXR-Danbury Municipal), located 7 mi (11.3 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into White Plains, NY (HPN-Westchester County), which is 23.1 mi (37.2 km) away.

If you prefer train travel, make your way to Brewster Train Station or Southeast Station and explore the city from there.

Frequently asked questions

What is the best area to stay in Brewster when booking a holiday rental?
When considering a holiday rental in Brewster, New York, the area around the town centre is particularly appealing. This neighbourhood offers a charming small-town atmosphere, making it a great base for exploring the surrounding region. Here, you'll find a variety of properties ranging from cozy cottages to spacious homes, suiting different preferences and group sizes.

One of the highlights of staying in this area is its proximity to the scenic Brewster Train Station, which is not only a functional transport hub but also a lovely spot to appreciate the local architecture. A short drive away, you can enjoy the picturesque lakes and hiking trails at nearby parks, great for outdoor enthusiasts. Additionally, the town is close to the stunning Putnam County Golf Course, which is a fantastic attraction for those looking to enjoy a round of golf amidst breathtaking views.

The neighbourhood also provides convenient access to local shops and eateries, allowing visitors to immerse themselves in the community's culture.
How much does it cost to rent a holiday home in Brewster?
Prices for holiday rentals in Brewster 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Brewster to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Brewster holiday house rentals?
You can find great discounts on house rentals in Brewster on Vrbo, 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.
What is the most popular type of holiday rental accomodation in Brewster?
In Brewster, cottages are the most popular type of holiday rental, with several available throughout the area. These charming properties often feature rustic interiors, cosy living spaces, and fully equipped kitchens, making them ideal for a home-away-from-home experience. Many cottages are set in picturesque surroundings, allowing guests to enjoy the natural beauty of the region.

Apartments are also commonly found in Brewster, providing a more compact option for travellers. These typically include essential amenities such as kitchen facilities and comfortable seating areas, superb for couples or solo adventurers. Additionally, there are several villas available, offering spacious rooms that often come with multiple bedrooms and outdoor spaces for relaxation.
Are there any family house rentals in Brewster?
In Brewster, New York, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The town is surrounded by beautiful natural landscapes and offers easy access to recreational activities. Many of these homes feature spacious interiors, full kitchens, and outdoor areas, great for family gatherings and barbecues.

Visitors can enjoy amenities such as Wi-Fi, air conditioning, and sometimes even game rooms or private gardens, providing plenty of space for kids to play. The nearby Putnam County offers various outdoor activities, including hiking trails and parks, which are ideal for family outings. Additionally, Brewster's charming downtown area features shops and dining options, enhancing the family experience.
Can I rent a holiday home with a pool or hot tub in Brewster?
In Brewster, New York, there are several holiday homes available for rent that feature pools and hot tubs, making it an appealing destination for travellers seeking relaxation and recreation. The area is known for its beautiful natural surroundings and proximity to scenic spots such as Lake Gleneida, where visitors can enjoy outdoor activities.

Many of the holiday rentals in Brewster offer amenities like private swimming pools, hot tubs, and spacious outdoor areas, great for unwinding after a day of exploring the local attractions. Additionally, these properties often come equipped with full kitchens and comfortable living spaces, suiting families or groups looking for a home away from home.
Can I find long-stay holiday rentals in Brewster?
A long-stay holiday rental in Brewster 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Brewster?
In Brewster, there are several pet-friendly house rentals available, making it a great choice for travellers looking to explore the area with their furry companions. Many of these holiday homes come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, providing a welcoming environment for both guests and pets.

The town is conveniently located near several parks, including the scenic Brewster Park, which offers walking paths and open spaces ideal for pet exercise and play. Additionally, the nearby Putnam County Trailway provides a lovely setting for walking or biking, allowing pets to enjoy the outdoors alongside their owners.
Are there any remote work holiday rentals in Brewster?
In Brewster, New York, there are approximately 12 holiday rentals that cater to remote workers, providing a conducive environment for those needing to balance work and leisure. Many of these properties are equipped with essential amenities such as high-speed Wi-Fi, dedicated desk spaces, and comfortable work areas, ensuring a productive atmosphere.

The picturesque surroundings of Brewster offer a peaceful retreat, with opportunities for outdoor activities like hiking in the nearby Appalachian Trail or enjoying the scenic views around the local lakes. Additionally, the charming town centre features quaint shops and eateries, adding convenience for those working remotely while also wanting to explore the local culture. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Brewster holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Brewster 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 on Vrbo 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.
What are popular rental amenities in Brewster?
In Brewster, popular rental amenities include cosy fireplaces, fully equipped kitchens, and inviting patios, making for a comfortable and home-like atmosphere. Many properties also feature books for leisurely reading and coffee or tea makers to enjoy a warm beverage while relaxing.
When is the best time to visit Brewster for a holiday rental?
The peak season for visiting Brewster typically spans from May to July, with July being the most popular month for holiday rentals. During this time, the warm weather invites visitors to partake in outdoor activities like hiking, biking, and exploring the beautiful nearby parks, making it an ideal period for travellers.

In July, you can expect delightful temperatures ranging from the mid-teens to mid-twenties Celsius, great for enjoying the scenic beauty of the area and engaging in leisurely pursuits, such as picnicking by the lakes or exploring local nature trails. The vibrant setting during this peak season is enhanced by community events and festivals, making it a lively time to experience Brewster's charm.

If you're looking for a more budget-friendly option, consider visiting in November. This month offers a serene atmosphere, allowing you to enjoy the tranquil beauty of Brewster without the hustle and bustle of peak tourist traffic. The crisp autumn air and stunning fall foliage create a picturesque setting for leisurely walks and scenic drives, all while benefiting from lower rental prices.
How early should I book a Brewster holiday rental?
Book your Brewster holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Brewster?
In Brewster, visitors can enjoy a mix of natural beauty and local charm. One of the main attractions is the nearby Candlewood Lake, great for outdoor activities such as fishing, boating, and picnicking along its scenic shores. The town is also home to the Brewster Historical Society, which offers insights into the area's rich history and heritage.

For those interested in nature, the nearby Putnam County Trailway provides excellent walking and biking paths through beautiful landscapes. The Appalachian Trail, accessible from Brewster, offers hiking opportunities with stunning views and a chance to explore the great outdoors.

Additionally, Brewster's quaint downtown area features local shops and eateries, providing a glimpse into the community's vibrant setting.
Can I change or cancel my Brewster home rental booking on Vrbo?
To find Brewster holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Brewster holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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