Brewster Vacation Rentals

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Tonight
Nov 12 - Nov 13
Tomorrow
Nov 13 - Nov 14
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation Rentals in Brewster

Property grounds
Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT

Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT

Brewster
9.2 out of 10, Wonderful, (7)
"Check in was easy. Pet friendly. Very spacious. Very clean 👌 👏. Pool was great. I was so happy the air conditioner was working great because it was 95 degrees. The property was near to shopping areas. I will stay again.."
United States
LaTisha B.
The price is ￥124,326
￥234,916 total
includes taxes & fees
Dec 10 - Dec 11
Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

Fishkill
9.6 out of 10, Exceptional, (45)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
United States
Lisa B.
The price is ￥39,902
￥51,413 total
includes taxes & fees
Nov 30 - Dec 1
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
9.8 out of 10, Exceptional, (126)
"I cannot say enough on this location. Peaceful, and the view was extraordinary. Highly recommend this to anyone that wants a getaway."
United States
Daniel R.
The price is ￥28,963
￥47,406 total
includes taxes & fees
Nov 16 - Nov 17
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Outdoor dining
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

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

New Fairfield
9.4 out of 10, Exceptional, (31)
"I stayed here for three nights with my elderly mom. The home is lovely and very comfortable, with lovely linens, updated bathrooms, and luxurious beds. The kitchen is wonderfully equipped for anything you might want to prepare. This would be an excellent spot for a family with children. The hosts were very responsive and gracious. Above all else, the view is absolutely spectacular. I wish i could wake up to it every day. I hope to go back in the fall when the leaves are changing. Highly...
United States
Virginia F.
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Dining
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

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

Brookfield
9.6 out of 10, Exceptional, (4)
"The host was very kind and welcoming. The home was spacious and the perfect setting for our celebration weekend. Everyone had their own space and we had multiple spaces for group activities. We enjoyed our time and appreciate the hospitality. "
United States
Valerie V.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Exterior
Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!

Fishkill
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is ￥46,603
￥69,640 total
includes taxes & fees
Nov 17 - Nov 18
Rustic Cabin in Fishkill!
Exterior
New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury

Southbury
9.8 out of 10, Exceptional, (16)
"Excellent stay !!!! Everything was perfect. Communication was phenomenal.!!!!"
United States
daniellle
The price is ￥13,865
￥19,026 total
includes taxes & fees
Nov 23 - Nov 24
New One Bedroom Apartment Centrally Located in Southbury
Interior
Contemporary Cozy Cottage

Contemporary Cozy Cottage

Lake Peekskill
10.0 out of 10, Exceptional, (30)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥34,664
￥65,197 total
includes taxes & fees
Nov 23 - Nov 24
Contemporary Cozy Cottage
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

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

Carmel Hamlet
10.0 out of 10, Exceptional, (94)
"We loved our stay. It was great for a family Thanksgiving"
United States
Edmund F.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Dining
Peaceful Vintage Home with Private Lake in Redding, CT.

Peaceful Vintage Home with Private Lake in Redding, CT.

2.0 star property
Redding
10.0 out of 10, Exceptional, (2)
"Property was beautiful in a very quiet and peaceful area. Our host Kadriia was so amazing and would respond so quickly to any questions we had and communicated clearly. My wife and our friends had a Halloween themed wedding party for our friends who couldn’t make it to the actual wedding and we couldn’t have had a better time. "
United States
Connor K.
The price is ￥55,462
￥90,434 total
includes taxes & fees
Nov 16 - Nov 17
Peaceful Vintage Home with Private Lake in Redding, CT.
Property grounds
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Danbury
10.0 out of 10, Exceptional, (24)
"Beautiful house with amazing views. Can’t wait to stay again. Great location too! Close to everything (shopping/food/activities) but located on a very quiet dead end. Owners were easy to communicate with and very friendly. "
United States
Mary M.
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Interior
Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.

Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.

Waccabuc
4.0 out of 10, (2)
"Clean but minimalist, big empty basement, good for a cheap stay near Caramoor"
United States
Patrick M.
The price is ￥22,678
￥31,436 total
includes taxes & fees
Nov 13 - Nov 14
Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.
Exterior
Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!

Highland Falls
9.8 out of 10, Exceptional, (19)
"Well equipped space and great communication from the host"
United States
Beth
The price is ￥27,661
￥45,997 total
includes taxes & fees
Dec 10 - Dec 11
Walk to WP Gate + Free Parking!
Children's area
Hickory on Willow Lake

Hickory on Willow Lake

Fishkill
9.6 out of 10, Exceptional, (4)
"We stayed one night. Would loved to have stayed longer. Beautiful property. "
United States
Christine B.
The price is ￥80,496
￥113,326 total
includes taxes & fees
Nov 25 - Nov 26
Hickory on Willow Lake
Terrace/patio
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

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

Holmes
10.0 out of 10, Exceptional, (196)
"A sweet little cabin on a quiet lake was exactly what I was looking for. My overall experience was absolutely wonderful."
United States
Janine H.
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
Outdoor dining
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

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

Croton-on-Hudson
9.6 out of 10, Exceptional, (15)
"Nice secluded place to get away"
United States
Orion O.
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Smart TV, fireplace, books
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

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

New Fairfield
10.0 out of 10, Exceptional, (14)
"Was a great find. Updated, spacious and clean."
United States
Paul B.
The price is ￥27,969
￥75,635 total
includes taxes & fees
Nov 16 - Nov 17
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
Fridge, microwave, oven, stovetop
Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!

Highland Falls
8.0 out of 10, Very Good, (2)
"Great place. Close to West Point activity. Clean and new."
United States
Joanne V.
The price is ￥26,691
￥50,407 total
includes taxes & fees
Nov 17 - Nov 18
Fabulous 3bdrm Home w/parking!
1 bedroom, WiFi, bed sheets
Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC

Carmel Hamlet
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is ￥18,729
￥40,512 total
includes taxes & fees
Nov 18 - Nov 19
Charming 1-bedroom apartment in Carmel with WiFi, AC
Outdoor dining
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

New Fairfield
9.8 out of 10, Exceptional, (35)
"We stayed for 3 weeks it was lovely!"
United States
Sarah T.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
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

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

10/10 Excellent
"Hotel alobby and Room were clean. Workout area had a good set of dumbells and cardio equipment."
Christian 1-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Find out more about Brewster

Search for holiday rentals in Brewster on Expedia! You can easily find your home rentals, villas, holiday apartments in Brewster using one of the methods below:

  • View our selection of featured holiday rentals in Brewster
  • Use the map to find apartments and other holiday homes in the Brewster neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Brewster while they last

Look no further and take a look at our great range of rental properties in Brewster!

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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental outside of Brewster offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and a coffee maker, 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 3 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.