A windmill in a grassy field with trees in the background.

Search Cottages in Brewster

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Brewster cottages

A two-story house with a wooden exterior, a front porch, and a staircase leading to the entrance.

1. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (25 reviews)
"Absolute comfortable stay. Everything you need and fantastic host!! Will be back."
United States
Lisa
The price is AED 617
AED 1,710 total
includes taxes & fees
15 Nov - 16 Nov
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A two-story house with a balcony, surrounded by lush greenery.

2. Quiet Solitude with Firepit, Electric Stove & Private Deck

Quiet Solitude with Firepit, Electric Stove & Private Deck
Hopewell Junction
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Sara's place. Unfortunately due to all the rain we couldn't enjoy the outside facilities. The bedroom loft is charming and everything you need is there. Thanks for a great stay!"
United States
stephanie a.
The price is AED 651
AED 1,963 total
includes taxes & fees
15 Nov - 16 Nov
Quiet Solitude with Firepit, Electric Stove & Private Deck
A house with a view of a bridge and mountains.

3. 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, (150 reviews)
"We had a great stay!!"
United States
Jasmine
The price is AED 727
AED 1,115 total
includes taxes & fees
16 Nov - 17 Nov
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A wooden deck with a railing overlooking a body of water and trees.

4. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (28 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is AED 918
AED 1,483 total
includes taxes & fees
13 Nov - 14 Nov
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A wooden deck with a railing overlooking a well-maintained lawn and trees.

5. Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
9.8 out of 10, Exceptional, (11 reviews)
"Beautiful setting, and plenty of room for a family of four. Accommodations were very clean and spacious. Thank you for hosting us!"
United States
Susan K.
The price is AED 1,154
AED 2,456 total
includes taxes & fees
29 Nov - 30 Nov
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Brewster Hotel Reviews

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"We had to wait two hours and a half for our dinner in the large hall. Not even tells us why it took so long."
Linda 1-night trip
Posted 1 hour ago
Overlook Lodge at Bear Mountain

Frequently asked questions

Why book your cottage in Brewster with Expedia?
Expedia has some superb cottages in Brewster, so get ready for an unforgettable vacation on nature's doorstep. If you have a budget, choose how much you're willing to spend and the star rating of your property. Or, use our handy filters to search for cottages with a kitchen or a pool. We'll help you find the right fit whatever your plans or style of travel.
How can I find cheap cottages in Brewster?
The best way to find cheap cottages in Brewster is with Expedia's handy filter tool. Tailor your search results by star rating, amenities and budget to snag excellent rates in a couple of clicks.