Brewster Vacation Rentals

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Vacation Rentals in Brewster

The Hideaway

10.0 out of 10, Exceptional, (4)
"Me and my family stayed here for a quick get-away out of the city. Very pretty location, and loved our stay here! Thanks!"
$287 nightly
The price is $311
Sep 14 - Sep 15
Total with taxes and fees
The Hideaway

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (28)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (29)
"Great place for a quiet stay"
$293 nightly
The price is $331
Sep 21 - Sep 22
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

8.8 out of 10, Excellent, (22)
"We were very happy with the accommodations. The cottage was neat, clean and well kept, as was the property. All the amenities were as described. We had a great weekend and would highly recommend this lake house."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (120)
"It has an incredible mountain and water view. "
$272 nightly
The price is $308
Sep 1 - Sep 2
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (87)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

9.8 out of 10, Exceptional, (7)
"Patrick and Katherine are excellent hosts with an incredible property in an amazing location. We had such an incredible time. The carriage house is so comfortable and welcoming. I absolutely loved just sitting on the balcony enjoying the beautiful view, birds, and my coffee. This was my first time using Vrbo, (glad to have found an alternative to another site I no longer support). Wow, I have been missing out!! The stocked fridge was such a lovely surprise. Everything was just fantastic. Our...
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
$369 nightly
The price is $419
Sep 2 - Sep 3
Total with taxes and fees
Rustic Cabin in Fishkill!

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

3.0 star property
10.0 out of 10, Exceptional, (2)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

10.0 out of 10, Exceptional, (191)
"We loved the house, it was very quiet, the view of the lake was beautiful (even though it was rainy and cloudy). The decoration was really nice and it felt super cozy. The host was also very responsive. "
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (45)
"Wonderful property with a great location."
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

10.0 out of 10, Exceptional, (11)
"The house worked very well for our family holiday. Very clean, had everything we needed "
$563 nightly
The price is $637
Sep 4 - Sep 5
Total with taxes and fees
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Private lake escape

Private lake escape

Litchfield County Four Season Country Paradise

9.6 out of 10, Exceptional, (48)
"Overall rating 5/5. I would recommend this home to other families and would stay again. "
Litchfield County Four Season Country Paradise

Spectacular Lake front house

9.6 out of 10, Exceptional, (4)
"This beautiful home offered plenty of space for our family of 6 adults and 2 children to enjoy a week together. "
Spectacular Lake front house

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (30)
"The property was everything it was advertised as. Nick and Jess reached out multiple times during our stay to make sure we had everything we needed, which we did. The home was large, comfortable and the kitchen lived up to the billing. The morning view from the upper bedroom areas over the lake was phenomenal. There was plenty of room for six adults and three kids and the bedrooms and bathrooms were very spacious. We loved the home, enjoyed the area and look forward to a stay again next year....
Lakeview Estate - Chef's Kitchen - NYC Getaway

Waterfront Family Retreat on Candlewood Lake

10.0 out of 10, Exceptional, (46)
"Wonderful! Elizabeth and John made everything seamless and enjoyable. Terrific location! "
$1,634 nightly
The price is $1,849
Sep 6 - Sep 7
Total with taxes and fees
Waterfront Family Retreat on Candlewood Lake

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (26)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT

10.0 out of 10, Exceptional, (13)
"Beautiful location and lots of space for a large group. This rental is really about the outdoor space and activities. Would love to return!"
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
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.
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Top Brewster Hotel Reviews

Find out more about Brewster

Find out more about Brewster

Everything you need to know about Brewster vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Brewster vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Brewster vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Brewster vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Brewster. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Brewster in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $308 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Brewster rentals

At Expedia, we put the best Brewster vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Brewster rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Brewster vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Brewster. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Brewster?

Yes, we offer vacation rentals close to popular local attractions in Brewster, or you can choose a 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's the top vacation rental that Brewster has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental outside of Brewster offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Brewster?

With 4 Expedia vacation rentals, you're sure 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 a family-friendly sight such as SplashDown Beach. Brewster Public Library and Centennial Golf Club are a couple of places you'll find in the larger area.

What’s a vacation rental in Brewster like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Brewster. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for families.