Title: Town of Lewisboro Vacation Home Rentals from CA $197: Search Top Private Vacation Homes for Rent | Expedia.ca

  

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# Town of Lewisboro Vacation Rentals

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## Check prices for these dates

Next weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Cities in Town of Lewisboro

![](https://mediaim.expedia.com/destination/2/f982fdf104102ad635b6a554672a811e.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Cross River

[](https://expedia.ca/Cross-River-Private-Vacation-Homes.d3000448270-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Featured Vacation Homes in Town of Lewisboro

![Property grounds](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/7ce63cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/32fb7c3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/c1311c5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/70b02142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Greenwich

9.6/10

Exceptional

(18)

"Perfect place to rest. Excellent service! "

![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg)

Lucymar

CA $94

CA $267 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Greenwich-Hotels-2-Bedroom-And-1-Full-Bath-In-Lakeside-Home-With-Private-Dock.h114606188.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75290000/75284500/75284422/4093dfa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75290000/75284500/75284422/3d4de8b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75290000/75284500/75284422/w1170h872x0y1-b8cb7f0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75290000/75284500/75284422/f51bbd29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Hopewell Junction

9.0/10

Wonderful

(42)

"The house is clean and nice. Location is really good, quiet and not to far from the city."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cecilia G.

[](https://www.expedia.ca/Hopewell-Junction-Hotels-1-HR-NYC-Getaway-Awesome-Newly-Renovated-Home-On-4-Acres.h75284422.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/98000000/97480000/97470900/97470860/9f8971d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/98000000/97480000/97470900/97470860/29e9c151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/98000000/97480000/97470900/97470860/f1288f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/98000000/97480000/97470900/97470860/9ac447c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Business or Weekend escape

Stratford

9.2/10

Wonderful

(50)

"Clean room, easy check-in, parking available on-site "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cindy

CA $112

CA $197 total

includes taxes & fees

Oct 28 - Oct 29

[](https://www.expedia.ca/Stratford-Hotels-Business-Or-Weekend-Escape.h97470860.Hotel-Information)

![Dining tables](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/7d1ae479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/0da715d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/ee5fa657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/113000000/112590000/112584800/112584776/377f36e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chestnut on Willow Lake

Fishkill

9.4/10

Exceptional

(3)

"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Doria W.

CA $560

CA $819 total

includes taxes & fees

Oct 28 - Oct 29

[](https://www.expedia.ca/Fishkill-Hotels-Charming-3-Bedroom-Cottage-In-Wonderful-Fishkill.h112584776.Hotel-Information)

![Children's area](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/b2662bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/244ebd87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/9d74f7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/3c974e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hickory on Willow Lake

Fishkill

9.6/10

Exceptional

(4)

"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rachel C.

CA $595

CA $865 total

includes taxes & fees

Oct 28 - Oct 29

[](https://www.expedia.ca/Fishkill-Hotels-Hickory-On-Willow-Lake.h112586795.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/113000000/112400000/112396200/112396103/6f9ea498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112400000/112396200/112396103/78231fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112400000/112396200/112396103/f0b6363b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112400000/112396200/112396103/671e1512.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom house with WiFi, AC in Fairfield

Fairfield

8.4/10

Very good

(9)

"Amalfi’s place was as described. It was clean and comfortable and mostly quiet. Amalfi was excellent with communication. Would certainly stay again when visiting family."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tom F.

CA $208

CA $485 total

includes taxes & fees

Nov 7 - Nov 8

[](https://www.expedia.ca/Fairfield-Hotels-Charming-2-Bedroom-House-With-WiFi.h112396103.Hotel-Information)

![Outdoor banquet area](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/76b5d504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/df2c75ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/e858b8f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/fe2ef847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Ossining

9.0/10

Wonderful

(6)

"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Matthew W.

[](https://www.expedia.ca/Ossining-Hotels-Castle-Cozy-Winter-Wonderland-Events.h101852343.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/95000000/94780000/94775200/94775128/618d1a43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94780000/94775200/94775128/b154cc6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/95000000/94780000/94775200/94775128/1b2cda6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/95000000/94780000/94775200/94775128/3a72d1f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

New Fairfield

9.4/10

Exceptional

(30)

"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

[](https://www.expedia.ca/New-Fairfield-Hotels-Lakehouse-Boat-Dock.h94775128.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71960000/71952400/71952323/f6623e06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71960000/71952400/71952323/550eef50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/72000000/71960000/71952400/71952323/0229fe97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/72000000/71960000/71952400/71952323/5aa43ade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Carmel Hamlet

10/10

Exceptional

(92)

"My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hector L.

[](https://www.expedia.ca/Carmel-Hotels-Lost-In-The-Woods.h71952323.Hotel-Information)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/cde347d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/8e1f1f20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/3089dd8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/101000000/100170000/100167400/100167349/23242491.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

New Fairfield

10/10

Exceptional

(13)

"The house worked very well for our family holiday. Very clean, had everything we needed "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Audrey P.

CA $319

CA $770 total

includes taxes & fees

Oct 28 - Oct 29

[](https://www.expedia.ca/New-Fairfield-Hotels-Peaceful-All-Season-Lake-Community-Home.h100167349.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/95000000/94940000/94940000/94939970/3ccd6435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/95000000/94940000/94940000/94939970/5a76e25b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/95000000/94940000/94940000/94939970/6720343b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/95000000/94940000/94940000/94939970/92e5b9ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stay at Black Rock Harbor

Black Rock Historic District

10/10

Exceptional

(24)

"Beautifully appointed home, comfortable furnishings, and fantastic location. We enjoyed the indoor and outdoor space, as well as the nearby beach, restaurants and freeway access. Everything was in fine working order and our stay was enjoyable! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeni B.

[](https://www.expedia.ca/Bridgeport-Hotels-Catch-Some-Zzz-At-Black-Rock-Harbor.h94939970.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/3138ca99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/2730f6d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/880d2845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/ebebe95b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterside

10/10

Exceptional

(5)

"Lovely little home in Stamford."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Pat A.

CA $220

CA $466 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Stamford-Hotels-Charming-2-Bedroom-House-In-Fabulous-Stamford-With-AC.h112364813.Hotel-Information)

![Miscellaneous](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345699/5209eb45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345699/1b3764d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345699/74e2f6c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 4-bedroom house in charming Rye with AC

Rye

CA $2,799

CA $3,479 total

includes taxes & fees

Oct 28 - Oct 29

[](https://www.expedia.ca/Rye-Hotels-Spacious-4-Bedroom-House-In-Charming-Rye-With-AC.h115345699.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/116000000/115680000/115677600/115677574/00c649a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115680000/115677600/115677574/c3a9ca25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115680000/115677600/115677574/8cf0af96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115680000/115677600/115677574/292fd06b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Brookfield

10/10

Exceptional

(2)

"This is a property that is very good for large family gatherings, which is how we gathered for a birthday celebration. This area of CT. is great and has lots to do.The house is in the perfect location to do all of it.Again, suits large groups well. Room for everyone."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paula R.

[](https://www.expedia.ca/Brookfield-Hotels-LakesideSleeps20HotTubGameRoom2AcresFirepit.h115677574.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/97000000/96850000/96842000/96841918/10c9994b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96850000/96842000/96841918/c9e7f08f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/97000000/96850000/96842000/96841918/8165e236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96850000/96842000/96841918/53df77e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

Nyack

9.0/10

Wonderful

(6)

"Large comfortable home in great location with multiple views of the Hudson. Our family had a pleasant stay and would definitely return to Castle in the Sky."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dr. Andrea W.

[](https://www.expedia.ca/Nyack-Hotels-Castle-In-The-Sky-Beautifully-Renovated-Victorian-One-Block-From-Main-St.h96841918.Hotel-Information)

![Smart TV, stereo](https://images.trvl-media.com/lodging/113000000/112050000/112048300/112048293/40355023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112050000/112048300/112048293/355638a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, stereo](https://images.trvl-media.com/lodging/113000000/112050000/112048300/112048293/7643b925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112050000/112048300/112048293/b5a9021c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

Bridgeport

9.6/10

Exceptional

(4)

"Very clean house. set up very nicely, landlord was very responsive and helpful. perfect for what we needed "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nancy H.

CA $1,008

CA $1,903 total

includes taxes & fees

Oct 28 - Oct 29

[](https://www.expedia.ca/Bridgeport-Hotels-Charming-Colonial-Retreat-Perfect-For-Family-Getaways.h112048293.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/121000000/120730000/120730000/120729940/2a65b106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120730000/120730000/120729940/91435553.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120730000/120730000/120729940/f41b18e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120730000/120730000/120729940/9a31e2b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Vintage Home with Private Lake in Redding, CT.

Redding

10/10

Exceptional

(1)

"Several of us stayed for one night for our kids soccer tournament. The home was spacious and had all the amenities needed to make our short stay comfortable. The host was very responsive and accommodating. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Annette H.

CA $693

CA $1,064 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Redding-Hotels-Spacious-5-Bedroom-House-In-Charming-Redding-With-The-Private-Lake.h120729940.Hotel-Information)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120870000/120863000/120862934/872038b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/121000000/120870000/120863000/120862934/3286c482.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120870000/120863000/120862934/w2128h1419x0y1-8c1b1aef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120870000/120863000/120862934/22f2526f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury NY Home with Game Room & Free Parking

White Plains

[](https://www.expedia.ca/White-Plains-Hotels-Luxury-NY-Home-With-Game-Room-Free-Parking.h120862934.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112100000/112096500/112096424/b893714f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112100000/112096500/112096424/0792229e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/113000000/112100000/112096500/112096424/14e0385b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112100000/112096500/112096424/1519aa82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-bedroom house with WiFi, AC in serene Fairfield

Fairfield

9.0/10

Wonderful

(9)

"Thank you for the stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Josh P.

[](https://www.expedia.ca/Fairfield-Hotels-Charming-3-Bedroom-House-With-WiFi.h112096424.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/e73b5292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/ee686000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/339c4da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/e5f1d678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### House on the Babbling Brook- Quiet 2BR + King Bed!

Highland Falls

10/10

Exceptional

(2)

"Good stay, awesome place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott G.

CA $186

CA $559 total

includes taxes & fees

Oct 28 - Oct 29

[](https://www.expedia.ca/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2025-11-10&endDate=2025-11-11&regionId=553248635976002127&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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Save an average of 15% on thousands of hotels when you're signed in

[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Lewisboro-Private-Vacation-Homes.d553248635976002127-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Lewisboro-Private-Vacation-Homes.d553248635976002127-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Town of Lewisboro Hotel Reviews

![Hampton Inn White Plains/Tarrytown](//images.trvl-media.com/lodging/1000000/30000/23300/23291/d5b0e16e_y.jpg)

### Hampton Inn White Plains/Tarrytown

10/10 Excellent

"The check in was quick and efficient. It was a very nice touch offering a selection of drinks and snacks! The room was clean abd comfortable. The bathroom is small but it is manageable. Breakfast offered many options which were readily available. Check out was also quick a d efficient. I would stay here again."

[](https://expedia.ca/White-Plains-Hotels-Hampton-Inn-White-Plains.h23291.Hotel-Information)

![Overlook Lodge at Bear Mountain](//images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg)

### Overlook Lodge at Bear Mountain

10/10 Excellent

"Clean room"

[](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information)

![Norwalk Inn & Conference Center](//images.trvl-media.com/lodging/1000000/20000/15200/15114/13ab5174_y.jpg)

### Norwalk Inn & Conference Center

10/10 Excellent

"Great place to stay"

[](https://expedia.ca/Stamford-Hotels-Norwalk-Inn.h15114.Hotel-Information)

![Hyatt Regency Greenwich](//images.trvl-media.com/lodging/1000000/20000/18200/18180/19d28016_y.jpg)

### Hyatt Regency Greenwich

10/10 Excellent

"Fabulous location next to great restaurants and shopping. Dramatic lobby, fabulous common spaces and fabulous bar. Half way between Greenwich and Stamford Ct. An architectural gem Close to Long Island Sound"

[](https://expedia.ca/Stamford-Hotels-Hyatt-Regency-Greenwich.h18180.Hotel-Information)

![DoubleTree by Hilton Stamford](//images.trvl-media.com/lodging/1000000/10000/5300/5292/f2f8be91_y.jpg)

### DoubleTree by Hilton Stamford

10/10 Excellent

"Very accommodating, clean and modern"

[](https://expedia.ca/Stamford-Hotels-Hilton-Stamford-Hotel-Executive-Meeting-Center.h5292.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Stamford / New York City](//images.trvl-media.com/lodging/1000000/30000/25000/24963/af81668d_y.jpg)

### La Quinta Inn & Suites by Wyndham Stamford / New York City

10/10 Excellent

"Liked the location. Needs updating, which you are now doing."

[](https://expedia.ca/Stamford-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Stamford-New-York-City.h24963.Hotel-Information)

![Tarrytown House Estate](//images.trvl-media.com/lodging/1000000/50000/49700/49674/a89a02a1_y.jpg)

### Tarrytown House Estate

10/10 Excellent

"Fantastic property and location. Incredible history and staff was helpful. "

[](https://expedia.ca/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information)

![The Stamford Hotel](//images.trvl-media.com/lodging/1000000/50000/42300/42258/d312d428_y.jpg)

### The Stamford Hotel

10/10 Excellent

"Very good place to stay "

[](https://expedia.ca/Stamford-Hotels-The-Stamford-Hotel.h42258.Hotel-Information)

![Hotel Nyack, a JdV by Hyatt Hotel](//images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/a38df02c_y.jpg)

### Hotel Nyack, a JdV by Hyatt Hotel

10/10 Excellent

"Very nice hotel!!! "

[](https://expedia.ca/Nyack-Hotels-Hotel-Nyack.h11943081.Hotel-Information)

## Find out more about Town of Lewisboro

## Town of Lewisboro Vacation Homes information

| Number of reviews | 309 |
| --- | --- |
| Accommodation | 437 Vacation Homes |
| Lowest Price | CA $197 |
| Highest Price | CA $3,479 |

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-   [Book Vacation Homes in Town of Lewisboro on Expedia.com](https://www.expedia.com/Town-Of-Lewisboro-Private-Vacation-Homes.d553248635976002127-aaPrivateVacationHomes.Travel-Guide-Accommodation)