Best Vacation Homes in Brewster
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $339/Night
For 7 Nights US $2,376
2766.32 ft²
9 Guests
4 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $248/Night
For 7 Nights US $1,738
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Balcony/Terrace
- Kitchen
- Parking
US $206/Night
For 7 Nights US $1,441
3 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Internet
- Child Friendly
US $151/Night
For 7 Nights US $1,054
US $187/Night
For 7 Nights US $1,307
520 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $516/Night
For 7 Nights US $3,614
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cabin
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $354/Night
For 7 Nights US $2,479
3000 ft²
11 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $824/Night
For 7 Nights US $5,771
Brewster Luxury Rentals
4800 ft²
19 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,539/Night
For 7 Nights US $10,773
16 Guests
11 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Pet Friendly
US $999/Night
For 7 Nights US $6,992
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $978/Night
For 7 Nights US $6,843
2769 ft²
9 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $572/Night
For 7 Nights US $4,003
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $565/Night
For 7 Nights US $3,953
2841.67 ft²
8 Guests
1 Bedroom
3 Bathrooms
House
- Fireplace/Heating
- Pool
- Parking
US $544/Night
For 7 Nights US $3,808
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Ski Chalet
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $484/Night
For 7 Nights US $3,387
2600 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $461/Night
For 7 Nights US $3,230
Brewster Pet Friendly Vacation Rentals
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $416/Night
For 7 Nights US $2,913
968.75 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $243/Night
For 7 Nights US $1,701
5 Guests
1 Bedroom
1 Bathroom
Pet Friendly
Apartment
- Pet Friendly
- Child Friendly
- Security/Safety
US $310/Night
For 7 Nights US $2,170
459.26 ft²
10 Guests
107 Bedrooms
1 Bathroom
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $409/Night
For 7 Nights US $2,863
2900 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $614/Night
For 7 Nights US $4,299
750 ft²
3 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $277/Night
For 7 Nights US $1,940
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Child Friendly
US $162/Night
For 7 Nights US $1,134
973 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $307/Night
For 7 Nights US $2,152
Brewster Large Vacation Homes
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $173/Night
For 7 Nights US $1,214
2700 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $601/Night
For 7 Nights US $4,210
8251 ft²
20 Guests
12 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
US $1,450/Night
For 7 Nights US $10,150
12 Guests
5 Bedrooms
6 Bathrooms
Family Friendly
House
- Breakfast
- Pet Friendly
- Child Friendly
US $1,250/Night
For 7 Nights US $8,750
6000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,102/Night
For 7 Nights US $7,713
US $467/Night
For 7 Nights US $3,269
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $858/Night
For 7 Nights US $6,008
10 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $682/Night
For 7 Nights US $4,773
Why Choose Rent By Owner for your Brewster Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Brewster
When should you plan your Vacation Rentals stay?
Choosing the best time to visit this region ensures you can enjoy its natural beauty and tranquility, making your stay in Brewster, New York, USA, truly memorable and stress-free.
Peak Season Highlights
Summer (June to August)
During the summer months, you'll experience warm weather ideal for outdoor activities and enjoying the scenic beauty of this destination.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Autumn offers vibrant foliage and pleasant weather, making it a perfect time to explore the area's natural landscapes and book cozy vacation rentals.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Winter (December to February)
The winter season brings cooler temperatures and fewer visitors, providing a more tranquil setting for your stay in the region.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
Spring (March to May)
In early spring, you'll find fewer crowds and a peaceful atmosphere as the area begins to awaken with new growth and mild weather.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Brewster
How to Book Your Brewster Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Brewster
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or deck perfect for relaxing and dining al fresco.
- Make the most of scenic views with outdoor seating areas that showcase the natural beauty of the area.
- Take advantage of spacious yards or gardens ideal for outdoor activities and family gatherings.
- Utilize well-maintained outdoor grills for barbecues during your stay in this charming destination.
- Use the outdoor pool, if available, to unwind and cool off during warm summer days.
- Explore nearby hiking trails or nature paths directly from your rental’s doorstep.
- Benefit from access to outdoor recreational facilities such as tennis courts or sports courts in the region.
Top Attractions Around Brewster
What attractions are nearby?
Within this scenic area, you can enjoy a variety of outdoor activities, explore charming local shops, and experience the natural beauty that makes Brewster a perfect destination for your next getaway.
Family Activities
- Brewster Ice Arena: Enjoy family-friendly ice skating sessions at this popular destination in the area, perfect for active fun indoors.
- Giant's Workshop Children's Museum: Engage your children with hands-on exhibits and interactive learning experiences designed specifically for young visitors here.
- Brookfield Conservation Area: Discover outdoor adventures with scenic walking trails and picnic spots that make for a relaxing day in nature.
- Putnam Trailway: Explore this scenic trail suitable for biking and walking, offering an excellent way to experience the natural beauty of the region with your family.
Adult Activities
- Brewster Historical Society Museum: Discover the rich history of the area through engaging exhibits and preserved artifacts that offer a glimpse into the region’s past.
- Skiing at Mount Peter Ski Area: Enjoy outdoor winter adventures by hitting the slopes at this popular nearby ski resort, ideal for both beginners and seasoned skiers.
- Golfing at Thunder Ridge Golf Club: Tee off amidst scenic views at this well-maintained golf course, perfect for relaxing afternoons in the region.
- Horseback Riding Tours: Explore the natural beauty of this destination on guided horseback rides that provide a unique perspective of the area's landscapes.
Other Places to Stay in Brewster, NY
Peach Lake
Town of Southeast
Brewster Public Library
Brewster Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the area's charming eateries to enjoy authentic regional cuisine during your stay.
- Plan Outdoor Activities: Make the most of the region's natural beauty by scheduling outdoor adventures such as hiking or nature walks around your rental.
- Visit Nearby Attractions: Discover popular local attractions close to your accommodation to enrich your experience here.
- Check Amenities and Accessibility: Ensure your vacation rental offers the comforts and conveniences you desire for a relaxing stay in this destination.
Transportation Options
- Metro-North Railroad: You can easily access commuter rail services from Brewster, connecting you to New York City and beyond for convenient regional travel.
- Local Bus Services: The regional bus options provide flexible transportation around the area, making it simple to explore here without a car.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing apps are available for quick, reliable transportation within this destination and nearby communities.
- Car Rentals: Renting a vehicle provides the freedom to explore more of the region at your own pace, with many companies offering service here for your convenience.
Local Customs Options
- Traditional Dutch-Inspired Homes: You will notice the region's charming Dutch influence reflected in many of the local architecture styles, adding a unique character to your stay.
- Seasonal Farm-to-Table Dining: During your visit, embracing the area's agricultural roots through seasonal, farm-fresh cuisine is a cherished custom for many residents and visitors alike.
- Community Festivals and Events: Participating in local festivals that celebrate the area's heritage offers a warm way to connect with the community during your vacation in this destination.
- Emphasis on Outdoor Recreation: The region encourages outdoor activities such as hiking and boating, reflecting the local appreciation for nature and active lifestyles.
Brewster Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Brewster?
There are a lot of options in Brewster. If you plan on staying in the Brewster area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Brewster:
- 6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED
- Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
- Charming Grand View/Lake Loft in Brewster with WiFi, AC
- Lakefront Brewster Vacation Rental w/Private Dock
- The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.
- Serene Hudson Valley Escape w/Pool & Grill
- The Hideaway
- Lux Haven Oasis retreat just 1 Hr from NYC Fully Furnished Rental in Carmel, NY!
- Lake Carmel Access Waterfront Home with Deck!
- Charming cottage on historic estate
2. How many vacation rentals have private pools in Brewster?
There are 3 vacation rentals with private pools near Brewster. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Brewster are best for families?
If you are looking for a family-friendly vacation home in Brewster, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Brewster:
4. How many Rentbyowner vacation rentals are available in Brewster?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 71 in the Brewster area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Brewster.
5. What is the cancellation policy for vacation rentals in Brewster, New York?
Cancellation policies vary by listing. Please review the specific property's policy on the listing page or contact the property owner directly for detailed information.
6. How do I find available dates and rates for vacation rentals in Brewster?
You can check availability and rates by entering your preferred travel dates on the property listing page. For personalized assistance, reaching out to the host is recommended.
7. Are there any specific house rules I should be aware of before booking?
Yes, each vacation rental includes specific house rules outlined in the listing. It’s important to review these details and communicate with the host if you have questions.
8. Is there a minimum stay requirement for booking in this area?
Minimum stay requirements vary between properties. You can find this information on the listing details or by contacting the property owner directly.
9. What amenities are typically included in a vacation rental here?
Amenities differ per property but commonly include essentials such as Wi-Fi, parking, and kitchen facilities. Check the individual listing for a complete list of available amenities.
Brewster Top Rated Vacation Rentals
432 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $203/Night
For 7 Nights US $1,421
288 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $217/Night
For 7 Nights US $1,519
2841 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $386/Night
For 7 Nights US $2,700
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
US $146/Night
For 7 Nights US $1,022
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Parking
US $279/Night
For 7 Nights US $1,950
306.77 ft²
14 Guests
34 Bedrooms
4 Bathrooms
Free Cancellation
Hotel
- Oceanfront
- Skiing
- Fireplace/Heating
US $160/Night
For 7 Nights US $1,120
US $140/Night
For 7 Nights US $982
US $120/Night
For 7 Nights US $841
