Top Town of Lewisboro Hotels: 2026 Best Hotels in Town of Lewisboro - Expedia

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Town of Lewisboro
New York
United States of America
Hotels
Expedia.com

Vacation Rentals in Town of Lewisboro Car Rentals in Town of Lewisboro Town of Lewisboro Vacations

A calm lake reflecting a forested hill during sunset.

A calm lake reflecting a forested hill during sunset.

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Top Cities in Town of Lewisboro

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Our top choices for Town of Lewisboro hotels

A lakeside view with a sandy beach, a row of blue Adirondack chairs, and a wooden dock extending into the water.

A spacious living area with a spiral staircase, a kitchen, and a large window offering a view of greenery.

A spacious living area with a high ceiling, a spiral staircase, a sofa, a floral armchair, and a dining area with a table and chairs.

A lakeside park with picnic tables, a wooden deck, and a walking path.

1. South Salem Vacation Rental w/ Furnished Deck!

South Salem Vacation Rental w/ Furnished Deck!

South Salem

9.6 out of 10, Exceptional, (7 reviews)

9.6/10

Exceptional

(7 reviews)

"Location was great! Look forward to using the deck more on future visits!"

"Location was great! Look forward to using the deck more on future visits!"

United States

elizabeth r.

South Salem Vacation Rental w/ Furnished Deck!

A large, two-story house with a stone wall in front, multiple windows, and a well-maintained lawn.

A hot tub in front of a house with a covered patio and a windowed room.

A spacious room with a large window, a rocking chair, and a framed artwork on the wall.

A spacious kitchen with a wooden table and bench, a chandelier, and large windows.

2. Over Sized Colonial on Private Road.

Over Sized Colonial on Private Road.

Pound Ridge

9.6 out of 10, Exceptional, (53 reviews)

9.6/10

Exceptional

(53 reviews)

"Perfect location and accommodations for our family gathering. "

"Perfect location and accommodations for our family gathering. "

United States

Linda J.

Over Sized Colonial on Private Road.

A spacious kitchen with a dining area, large windows, and potted plants.

A spacious living room with a leather sofa, a glass coffee table, and a fireplace.

A spacious living room with a large window, a wooden dining table, and a cozy seating area.

An outdoor patio with a fire pit, wooden chairs, and a table set for dining.

3. Peaceful Light-Filled Guesthouse salt pool/sauna - 1 Hour From NYC

Peaceful Light-Filled Guesthouse salt pool/sauna - 1 Hour From NYC

Pound Ridge

10.0 out of 10, Exceptional, (10 reviews)

10/10

Exceptional

(10 reviews)

"Great stay all around. Beautiful accommodation and property. Excellent communication from host. "

"Great stay all around. Beautiful accommodation and property. Excellent communication from host. "

United States

Bobby R.

Peaceful Light-Filled Guesthouse salt pool/sauna - 1 Hour From NYC

A modern living room with a stone fireplace, a sofa, a coffee table, and a TV.

A modern living room with a grey sofa, a white coffee table, and a patterned rug.

A modern kitchen with white appliances, a stone fireplace, and a dining area with a view.

A park with a playground, picnic tables, and a lake.

4. Pet Friendly Lake Cottage w/Fireplace & Fire Pit W/D

Pet Friendly Lake Cottage w/Fireplace & Fire Pit W/D

North Salem

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

"House was clean. The only problem was there was nowhere to put clothes in bedrooms or a nightstand/ bedside lamp. Otherwise house was nice. "

"House was clean. The only problem was there was nowhere to put clothes in bedrooms or a nightstand/ bedside lamp. Otherwise house was nice. "

United States

Brian S.

Pet Friendly Lake Cottage w/Fireplace & Fire Pit W/D

A modern living room with a sectional sofa, a coffee table, and a fireplace.

An outdoor dining area with a table set for four, surrounded by chairs, under a large umbrella.

A modern kitchen with white cabinetry, a stainless steel refrigerator, a marble countertop, and a built-in island with a sink.

A bedroom with a bed, nightstand, lamp, and a door.

5. Waccabuc Lake House by Avantstay Lakefront + Pool + Kayak Fish the Lake

Waccabuc Lake House by Avantstay Lakefront + Pool + Kayak Fish the Lake

3.0 star property

Waccabuc

Waccabuc Lake House by Avantstay Lakefront + Pool + Kayak Fish the Lake

A sandy beach with a bench and a small table, overlooking a calm lake with trees in the background.

A garden pathway with a pergola structure and blooming pink flowers.

A dining area with a round table, four chairs, a chandelier, a clock, and a large window with a view of trees.

A kitchen with wooden flooring, a stainless steel trash bin, and a chandelier.

6. Historic Hideaway with Lake Access!

Historic Hideaway with Lake Access!

South Salem

9.8 out of 10, Exceptional, (29 reviews)

9.8/10

Exceptional

(29 reviews)

"Awesome antique cottage…great location!!We didn’t want to leave!"

"Awesome antique cottage…great location!!We didn’t want to leave!"

United States

Kari W.

Historic Hideaway with Lake Access!

A two-story house with a stone facade, a central entrance with a wooden door, and a stone chimney. There are two small windows on the upper floor and a covered porch with columns.

A dining room with a wooden table, white chairs, a patterned rug, and a chandelier.

A poolside area with lounge chairs, umbrellas, and a clear view of the surrounding landscape.

A modern kitchen with white cabinetry, a marble island, stainless steel appliances, and a large window providing natural light.

7. Outdoor Entertainment Areas: Spacious Katonah Gem!

Outdoor Entertainment Areas: Spacious Katonah Gem!

3.0 star property

Katonah

Outdoor Entertainment Areas: Spacious Katonah Gem!

A modern house with a sloped roof, large windows, and a stone pathway leading to the entrance.

A kitchen with wooden cabinets, a large island, and pendant lighting.

A spacious living room with a stone fireplace, wooden beams, a flat-screen TV, and a dining area in the background.

A patio area with a wooden deck, outdoor seating, and a grill.

8. beautiful contemporary house , only one hour from Manhattan

beautiful contemporary house , only one hour from Manhattan

Pound Ridge

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

"This is a wonderful oasis tucked into the quiet and peaceful woods in Pound Ridge. So quiet and seemingly remote and yet minutes from excellent restaurants and shopping."

"This is a wonderful oasis tucked into the quiet and peaceful woods in Pound Ridge. So quiet and seemingly remote and yet minutes from excellent restaurants and shopping."

United States

Michael E.

beautiful contemporary house , only one hour from Manhattan

A modern kitchen with white cabinetry, a blue island, and a skylight.

A modern living room with a sofa, a coffee table, a TV mounted on the wall, and a window with a view of trees.

A covered patio with a white table set for dining, surrounded by white chairs, and a bench.

A dining area with a wooden table, blue upholstered chairs, and a chandelier.

9. Private Pool + Swim + Fish the Lake + Kayak | Waccabuc Lake House

Private Pool + Swim + Fish the Lake + Kayak | Waccabuc Lake House

Waccabuc

Private Pool + Swim + Fish the Lake + Kayak | Waccabuc Lake House

A stone staircase leading up to a building with large windows.

A cozy room with a wooden ceiling, a large window with a view of trees, a bookshelf, a sofa, a chair, and a table with books.

A cozy room with a wooden ceiling, a round table with books and a globe, a chair, a vase with flowers, and a window with a view of trees.

A cozy reading nook with a green armchair, a wooden desk, a bookshelf, and a large window with natural light.

10. Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

Pound Ridge

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"A cozy, well-maintained cottage, conveniently located near our son and his family who we were visiting. Modern appliances in the kitchen. Exterior and interior were as shown on VRBO. The property manager and owner were very helpful whenever we needed anything. Highly recommended. We would definitely like to stay here again whenever we visit our son."

"A cozy, well-maintained cottage, conveniently located near our son and his family who we were visiting. Modern appliances in the kitchen. Exterior and interior were as shown on VRBO. The property manager and owner were very helpful whenever we needed anything. Highly recommended. We would definitely like to stay here again whenever we visit our son."

United States

Peter B.

Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

A historic stone building with a turret, arched entrance, and a covered patio area.

A spacious lobby with a high ceiling, patterned walls, and a central seating area with ottomans and a coffee table.

A spacious lobby with a staircase, seating area, and large windows offering a view of the outdoors.

A large building with a white facade and columns, surrounded by a lawn with outdoor seating and string lights.

11. Tarrytown House Estate

Tarrytown House Estate

3.5 star property

Tarrytown

8.2 out of 10, Very good, (1,356 reviews)

8.2/10

Very good

(1,356 reviews)

"The grounds were beautiful and the staff was great."

"The grounds were beautiful and the staff was great."

United States

Denise

$181 nightly

The price is $207

$207 total

Nov 8 - Nov 9

Total with taxes and fees

Tarrytown House Estate

A spacious room with a stone fireplace, white sofas, and a large window offering a view of the outdoors.

An outdoor patio with tables and chairs, surrounded by large umbrellas.

A modern building with a stone facade and wooden beams, surrounded by a well-maintained lawn and trees.

A spacious corridor with stone walls, large windows, and a central chandelier.

12. Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham

3.5 star property

Tarrytown

7.0 out of 10, Good, (1,002 reviews)

7.0/10

Good

(1,002 reviews)

"Beautiful hotel with friendly staff"

"Beautiful hotel with friendly staff"

United States

Michelle

$143 nightly

The price is $164

$164 total

Nov 1 - Nov 2

Total with taxes and fees

Sleepy Hollow Hotel, a Dolce by Wyndham

A checkered floor, a potted plant, and two metal ladders in a room with large windows.

A modern building with a glass facade, surrounded by a landscaped garden with various plants and a classical-style urn.

A modern office space with a large desk, multiple printers, and comfortable seating.

A hotel lobby with a sofa, armchairs, a glass table, and lamps.

13. West Gate Inn Nyack

West Gate Inn Nyack

3.0 star property

Nyack

7.4 out of 10, Good, (1,469 reviews)

7.4/10

Good

(1,469 reviews)

"It was a great stay. Hotel was well equipped and came with lovely breakfast."

"It was a great stay. Hotel was well equipped and came with lovely breakfast."

United States

Stuart

$90 nightly

The price is $103

$103 total

Oct 20 - Oct 21

Total with taxes and fees

West Gate Inn Nyack

A spacious dining area with multiple tables and chairs, a stone wall with a mounted deer head, and a fireplace.

A large, multi-story stone building with a prominent arched entrance and multiple windows.

A wooden reception desk with a man standing behind it, a staircase, and a wooden interior.

A large outdoor swimming pool surrounded by trees and a covered pavilion.

14. Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property

Bear Mountain

8.4 out of 10, Very good, (1,001 reviews)

8.4/10

Very good

(1,001 reviews)

"Very nice place to stay. Very beautiful"

"Very nice place to stay. Very beautiful"

United States

Lawrence

$99 nightly

The price is $117

$117 total

Nov 9 - Nov 10

Total with taxes and fees

Overlook Lodge at Bear Mountain

A modern kitchen with a large island, bar stools, a flat-screen TV, and a stone backsplash.

A gym with treadmills, elliptical machines, and weightlifting equipment.

A snack and beverage vending area with a refrigerator and shelves stocked with various snacks and drinks.

A lobby with teal patterned chairs, a fireplace, and a flat-screen TV mounted above it.

15. Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3.0 star property

Elmsford

8.0 out of 10, Very good, (1,713 reviews)

8.0/10

Very good

(1,713 reviews)

"Nice hotel and great staff"

"Nice hotel and great staff"

United States

James

$122 nightly

The price is $140

$140 total

Nov 1 - Nov 2

Total with taxes and fees

Hampton Inn White Plains/Tarrytown

A modern bar area with a bar counter, multiple stools, and a seating area with a sofa and chairs.

A modern building with a glass facade, a red door, and a staircase leading to the entrance.

Room

A modern dining area with a wooden table, cushioned seating, pendant lighting, and a large window offering a view of the outdoors.

16. Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

4.0 star property

Nyack

8.6 out of 10, Excellent, (1,318 reviews)

8.6/10

Excellent

(1,318 reviews)

"Great hotel!"

"Great hotel!"

United States

Jessica

$136 nightly

The price is $155

$155 total

Nov 15 - Nov 16

Total with taxes and fees

Hotel Nyack, a JdV by Hyatt Hotel

A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.

A hotel corridor with a patterned carpet, a railing, and a reception desk with a glass partition.

A hotel room with a large bed, a desk, and a chair. There is a window with curtains and a wall with a geometric patterned design.

A modern hotel lobby with a seating area, a kitchen, and a bar.

17. Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 star property

Elmsford

8.4 out of 10, Very good, (1,886 reviews)

8.4/10

Very good

(1,886 reviews)

"Really close to everything to do in Sleepy Hollow for a great price and very nice!"

"Really close to everything to do in Sleepy Hollow for a great price and very nice!"

United States

Amanda

$137 nightly

The price is $156

$156 total

Nov 1 - Nov 2

Total with taxes and fees

Baymont by Wyndham White Plains - Elmsford

A spacious lobby with a reception desk, sofas, and a coffee table. There are multiple seating areas and a large window providing natural light.

A gym with exercise equipment, large windows, and a wooden reception desk.

A Sheraton hotel with a modern facade, multiple floors, and a prominent entrance.

An indoor swimming pool with a 3 feet 10 inches deep sign, surrounded by a white tiled area, benches, and a glass door leading to another room.

18. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel

3.5 star property

Tarrytown

8.4 out of 10, Very good, (1,006 reviews)

8.4/10

Very good

(1,006 reviews)

"Nice stay"

"Nice stay"

United States

Kerry-Anna

$143 nightly

The price is $164

$164 total

Nov 1 - Nov 2

Total with taxes and fees

Sheraton Tarrytown Hotel

A spacious lobby with a high ceiling, wooden beams, a central green wall with plants, seating areas, and a bar.

A spacious indoor area with multiple seating arrangements, including sofas and round tables, and a central decorative table with flowers.

A modern hotel lobby with a self-service beverage station, a small refrigerator, and a reception desk.

A spacious atrium with a central water feature, multiple seating areas, and a bar.

19. Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 star property

Suffern

9.0 out of 10, Wonderful, (1,050 reviews)

9.0/10

Wonderful

(1,050 reviews)

"An excellent location for the purpose of our visit - clean and quiet with a very helpful staff."

"An excellent location for the purpose of our visit - clean and quiet with a very helpful staff."

United States

mary

$122 nightly

The price is $142

$142 total

Nov 15 - Nov 16

Total with taxes and fees

Crowne Plaza Suffern - Mahwah by IHG

An outdoor seating area with wicker chairs and tables, surrounded by greenery and a modern lamp structure.

A modern lobby with a reception desk, seating area, and a kitchen in the background.

A formal dining setup with multiple tables, each set with clear glassware, plates, and cutlery.

Lounge

20. Westchester Marriott

Westchester Marriott

4.5 star property

Tarrytown

9.0 out of 10, Wonderful, (671 reviews)

9.0/10

Wonderful

(671 reviews)

$197 nightly

The price is $225

$225 total

Nov 1 - Nov 2

Total with taxes and fees

Westchester Marriott

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.

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 Town of Lewisboro Hotel Reviews

Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent

"Really enjoyed the hotel"

Katherine 1-night trip

Posted 1 hour ago

Hyatt Regency Greenwich

The Circle Hotel Fairfield

The Circle Hotel Fairfield

10/10 Excellent

"We didn't use much of the amenities so I cannot speak to that but the bed was the comfiest bed we've ever experienced. The front desk were friendly and the room was clean. The remote check-in/check-out was super convenient, too. We will absolutely stay again when visiting family."

Caeleigh 1-night trip

Posted 3 days ago

The Circle Hotel Fairfield

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