A calm lake reflecting a forested hill during sunset.

Cottages in Town of Lewisboro

Compare and save

  • 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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Town of Lewisboro cottages

A spacious living room with a fireplace, a television, and a dining area.

1. Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT

Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Bethel
10.0 out of 10, Exceptional, (18 reviews)
"Just a wonderful place to stay! We will be back…"
United States
Carole R.
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
A house with a view of a bridge and mountains.

2. 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, (147 reviews)
"We had a great stay!!"
United States
Jasmine
The price is AED 727
AED 1,215 total
includes taxes & fees
6 Oct - 7 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A covered porch with a light green door, white railings, and a mailbox.

3. Cozy 2-bedroom cottage in peaceful Danbury with AC

Cozy 2-bedroom cottage in peaceful Danbury with AC
Danbury
10.0 out of 10, Exceptional, (1 review)
"We were in town for Christmas with the family. The house was a perfect fit for us and the host responded almost immediately whenever we reached out to him. The house looks like a new renovation, and they did not skimp on finishings - very well done. It was very cold outside, but nice and warm inside. The snow didn’t slow us down. Great spot, will have to come back in the summer to enjoy the lake. Highly recommended! Thanks for letting us stay!!"
United States
Thomas H. H.
Cozy 2-bedroom cottage in peaceful Danbury with AC
A view from a boat deck with a metal railing, a bench, and a circular table.

4. Magnificent View on Whaley Lake

Magnificent View on Whaley Lake
Holmes
10.0 out of 10, Exceptional, (1 review)
"Great Place to stay, and friendly host!"
United States
Noah L.
Magnificent View on Whaley Lake
A wooden deck with a railing overlooking a body of water and trees.

5. 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, (24 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 1,563 total
includes taxes & fees
5 Oct - 6 Oct
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A two-story house with a wooden exterior, a front porch, and a staircase leading to the entrance.

6. 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)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A modern two-story house with a paved driveway, a stone wall, and a small outdoor seating area.

7. Charming Studio-Cottage with WiFi & TV free parking in Greenwich

Charming Studio-Cottage with WiFi & TV free parking in Greenwich
Greenwich
9.0 out of 10, Wonderful, (2 reviews)
"Excellent stay"
United States
Kathleen C.
Charming Studio-Cottage with WiFi & TV free parking in Greenwich
A building with a covered porch, a chimney, and a tree in the background.

8. Westport "Gold Coast" across from Southport beach

Westport "Gold Coast" across from Southport beach
Fairfield
10.0 out of 10, Exceptional, (104 reviews)
"Everything was wonderful, love staying there. "
United States
Shelley M.
Westport "Gold Coast" across from Southport beach
A wooden house with a stone pathway leading to a wooden deck.

9. Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC

Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Greenwich
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful and restful"
United States
Lisa H.
The price is AED 3,287
AED 6,161 total
includes taxes & fees
2 Nov - 3 Nov
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
A hot tub with a view of a forested area.

10. Great Fall pricing! Magical Views & Peaceful Vibes; private dock, kayaks, firepit, office!

Great Fall pricing! Magical Views & Peaceful Vibes; private dock, kayaks, firepit, office!
Newtown
8.8 out of 10, Excellent, (5 reviews)
"Charming cabin, great location… comfy and cozy"
United States
MaryJane B.
Great Fall pricing! Magical Views & Peaceful Vibes; private dock, kayaks, firepit, office!
A snow-covered landscape with a house in the background.

11. Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?

Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Weston
10.0 out of 10, Exceptional, (16 reviews)
"Wonderful stay!"
United States
james v.
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a wooden dining table with two chairs.

12. Stylish Loft with Parking Near NYC + Hospital

Stylish Loft with Parking Near NYC + Hospital
West Side
9.6 out of 10, Exceptional, (18 reviews)
"I stayed there for 3 nights while my place was being worked on. This place is a no brainer! It was even perfect since we had two cats. They appreciated the quite environment. The place was clean, well kept, and fairly modern. The host was super responsive we I needed them. Get this instead of a hotel it's, also uper spacious."
United States
Jerrydsen
Stylish Loft with Parking Near NYC + Hospital
A rustic cabin nestled in a forest, surrounded by lush greenery and a stone wall.

13. Lakefront Brewster Vacation Rental w/ Private Dock

Lakefront Brewster Vacation Rental w/ Private Dock
Brewster
10.0 out of 10, Exceptional, (15 reviews)
"We had a wonderful stay"
United States
SALVATORE D.
Lakefront Brewster Vacation Rental w/ Private Dock
A deck with wicker furniture, a table with a vase, and a large umbrella.

14. Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Putnam Valley
9.6 out of 10, Exceptional, (16 reviews)
"Beautiful property and a wonderful host. Would definitely stay here again. "
United States
Heather T.
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
A white building with a porch, a vehicle parked in front, and a stone wall.

15. Cos Cob Cottage- Full Kitchen, Pet Friendly

Cos Cob Cottage- Full Kitchen, Pet Friendly
Greenwich
9.6 out of 10, Exceptional, (5 reviews)
"Great Property. Driveway parking a bit of a challenge"
United States
Janet L.
Cos Cob Cottage- Full Kitchen, Pet Friendly
A wooden deck with a railing overlooking a well-maintained lawn and trees.

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

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
9.6 out of 10, Exceptional, (9 reviews)
"lovely porch and backyard."
United States
Kaia W.
The price is AED 1,466
AED 3,840 total
includes taxes & fees
4 Nov - 5 Nov
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
A two-story house with a white picket fence, a garage, and a tree in front.

17. Nama-stay, sweet pink Saugatuck Shores beach cottage

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.2 out of 10, Wonderful, (17 reviews)
"Great fenced in yard for our pup"
United States
Deb S.
Nama-stay, sweet pink Saugatuck Shores beach cottage
A covered outdoor seating area with a table, chairs, and a bench.

18. Pet-Friendly Cottage, 2 Mi to Saugatuck Falls

Pet-Friendly Cottage, 2 Mi to Saugatuck Falls
Redding
8.0 out of 10, Very good, (3 reviews)
"Host was very communicative and helpful. "
United States
Jaclyn N.
Pet-Friendly Cottage, 2 Mi to Saugatuck Falls
A single-story house with a garage, a front lawn, and a small garden area.

19. Cozy Lake Community Cottage with private beach & hot tub - ideal for long stays

Cozy Lake Community Cottage with private beach & hot tub - ideal for long stays
New Fairfield
10.0 out of 10, Exceptional, (3 reviews)
"Lovely little 2/2 house in a great location with just about everything we needed. Very quiet too. Our host, Jonathan was very responsive when we had questions or concerns. We would highly recommend!"
United States
Mary Anne O.
Cozy Lake Community Cottage with private beach & hot tub - ideal for long stays
A residential area with houses, a driveway, and a view of the sea.

20. Charming Fairfield Beach Cottage

Charming Fairfield Beach Cottage
Fairfield Beach
10.0 out of 10, Exceptional, (36 reviews)
"Overall a very smooth and enjoyable experience. "
United States
Dora M.
Charming Fairfield Beach Cottage
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 Town of Lewisboro Hotel Reviews

Amsterdam Hotel

Amsterdam Hotel

10/10 Excellent
"We love this hotel! It is our "go to" place to stay when we are in the area. It's extremely affordable and clean. The staff is super friendly and helpful. Its also walking distance to the train station, we stayed here and took the train to NYC. Great stay!!"
Angie 1-night trip
Posted 1 hour ago
Amsterdam Hotel

Explore a world of travel with Expedia