Brewster Holiday Rentals

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Holiday Rentals in Brewster

The Hideaway
10.0 out of 10, Exceptional, 1 review
"We enjoyed our short stay with Renee, who was very helpful! Plenty of room for our XL dogs to walk - ( 90lbs and 188lbs). Thank you for your hospitality! We’ll see you again, if we’re in the area!"
The price is NZ$450
includes taxes & fees
2 Jun - 3 Jun
The Hideaway
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, 35 reviews
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, 35 reviews
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
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Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, 96 reviews
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is NZ$473
includes taxes & fees
10 Jun - 11 Jun
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, 75 reviews
"We had such an awesome stay! Check in process was easy! Amazing scenery amazing adventure we had with our two furr babies!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, 58 reviews
"Property manager was very kind and responsive. Greatly enjoyed the views of the pond and the basement pool and ping pong tables. Great time playing these games with mybson as the weather wasn't conducive for water activities."
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Westport Beach Town Mid-Century Vibe Retreat - Pet friendly, walk to downtown shops & restaurants
Westport Beach Town Mid-Century Vibe Retreat - Pet friendly, walk to downtown shops & restaurants
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, 17 reviews
"My husband, dog and I had a great Memorial Day weekend at this lakeside property. The house is a short drive away from NYC and is situated perfectly between the quaint towns of Ridgefield and Katonah. We had a good time enjoying the lake and nearby hikes."
Serenity Awaits at this Cozy Lakeside Bungalow
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, 74 reviews
"For the groomsman it was perfect crazy fun."
Spectacular Short Term Vacation Rental in Kent
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, 17 reviews
"The property is lovely and well prepared for guests. The location is wonderful. One of our highlights was watching a bald eagle soar over the lake."
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, 8 reviews
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, 21 reviews
"This house has an ideal location to see lots of local sites of interest in the Hyde Park and Poughkeepsie area. Easy trip from there to West Point, Hyde Park and the Culinary Institute from the location, and great restaurant, Tiramasu, is very close. The house is immaculate! The beds were very comfortable, linens were provided, the bathrooms were spacious and the five of us had plenty of room for our toiletries. The house has steps to its multiple levels for all essential rooms, not accessible....
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, 168 reviews
"If you need a relaxing few days in the winter, very good place. Great views and quiet is the key."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Lake Luxury
10.0 out of 10, Exceptional, 8 reviews
"We loved our stay at this home. Plenty of space so we didn’t feel like we were on top of each other, gorgeous kitchen (plus a separate butler’s kitchen!), and lux bathrooms made this rental exactly what we needed. Thanks Gianna!"
Lake Luxury
Peaceful apartment on 3.5 acres w/ artist studio.
10.0 out of 10, Exceptional, 11 reviews
"Cute."
The price is NZ$348
includes taxes & fees
10 Jun - 11 Jun
Peaceful apartment on 3.5 acres w/ artist studio.
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, 16 reviews
"What a beautiful home with a spectacular view. We had the most relaxing, fun filled vacation!! The amenities were over and beyond what any of us ever expected."
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, 18 reviews
"We had a very pleasant stay! We came for our son’s graduation from West Point. Pat was a gracious host and made sure that we had up to date info. There were lots of thoughtful amenities, the beds and couches were very comfortable, we used the grill and sat on the deck which overlooks a wooded hill. The location is peaceful and in the country just down the street from a horse pasture. You can hear the brook bubbling across the way. The WiFi worked great and although there is just a window air...
The price is NZ$473
includes taxes & fees
30 Jun - 1 Jul
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Adorable 1-Bedroom Cottage in Weston, CT
10.0 out of 10, Exceptional, 26 reviews
"Everything was extremely lovely. The location is so beautiful and the house is very quaint and cozy, loved it!"
The price is NZ$487
includes taxes & fees
21 Jun - 22 Jun
Adorable 1-Bedroom Cottage in Weston, CT
Lakefront New York Abode w/ Deck, Grill & Fire Pit
9.6 out of 10, Exceptional, 4 reviews
"Clean, spacious, and many activities in a nice quiet town. The house comfortably fit our 10 people."
Lakefront New York Abode w/ Deck, Grill & Fire Pit
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See all available properties in Brewster
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.

Other types of properties in Brewster you may be interested in

Comfort Inn
2.5 star property
8.8 out of 10, Excellent, 303 reviews
"Our refrigerator is not working luckily we booked two rooms and stored our refrigerated items there. We have not let management know, but will notify them in the morning. Good night."
The price is NZ$261
includes taxes & fees
16 Jun - 17 Jun
Comfort Inn
Heidi's Inn
2.5 star property
8.6 out of 10, Excellent, 580 reviews
"We spent four nights over the Memorial Day weekend 2024. The room, the property grounds and dining area were very clean and well maintained. The stuff was friendly and very helpful. The pool did not work though but they will fix it. We definitely will come back soon!"
The price is NZ$221
includes taxes & fees
6 Jun - 7 Jun
Heidi's Inn
EVEN Hotel Norwalk, an IHG Hotel
3.5 star property
8.2 out of 10, Very good, 1,001 reviews
"We had to book the last minute. Our reservation for a Vrbo booking had been cancelled. The customer service representative found an available room at the Even Hotel in Norwalk. Check in was quick. The room was comfortable and clean. I really appreciated the friendly staff. "
The price is NZ$254
includes taxes & fees
6 Jun - 7 Jun
EVEN Hotel Norwalk, an IHG Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Brewster holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Brewster. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Brewster. Seeing all the best attractions is bound to make you fall in love with Brewster. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Brewster short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Brewster?

Yes, there are holiday rentals close to the most popular sights in Brewster, or you can select a more secluded option if you're looking for a relaxing stay. Brewster is known for its shopping and restaurants. Make sure you have time to check out the entertainment choices and live music during your trip.

What are some of the best holiday rentals that Brewster has to offer?

Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond: This holiday home rental outside of Brewster is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Brewster?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Brewster stay.

What’s there to see and do in Brewster?

Explore the area and cultural attractions such as Kouros Sculpture Center, or visit one of the family-friendly sights such as SplashDown Beach. Brewster Public Library and Matrix Conference and Banquet Center are a couple of places you'll find in the wider area.

What’s a holiday rental in Brewster like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Brewster. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.

Recent reviews of Brewster properties
Expedia verified reviews