Title: Town of Lewisboro Villas from CA $2,190 | Expedia.ca [Town of Lewisboro Hotels](https://expedia.ca/Destinations-In-Town-Of-Lewisboro.d553248635976002127.Hotel-Destinations)[Vacation Rentals in Town of Lewisboro](https://expedia.ca/Destinations-In-Town-Of-Lewisboro.d553248635976002127.Vacation-Rental-Destinations)[Town of Lewisboro Car Rentals](https://expedia.ca/Destinations-In-Town-Of-Lewisboro.d553248635976002127.Car-Rental-Destinations)[Town of Lewisboro Vacations](https://expedia.ca/Town-Of-Lewisboro.d553248635976002127.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/f982fdf104102ad635b6a554672a811e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Marina Timo # Search Town of Lewisboro Villa Rentals from CA $2,190 ## Compare and save - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VILLA&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-Villas.d3000448270-aaVillas.Travel-Guide-Accommodation) ## Featured Villas in Town of Lewisboro ![Exterior](https://images.trvl-media.com/lodging/120000000/119730000/119724400/119724381/9959c91a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119730000/119724400/119724381/c5ab9006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/120000000/119730000/119724400/119724381/45d643be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119730000/119724400/119724381/3e1f9309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 6 BR Mansion , Celebration Welcomes Norwalk 10/10 Exceptional (2) "Lots of space and very convenient " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael J. [](https://www.expedia.ca/Norwalk-Hotels-6-BR-Mansion.h119724381.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118870000/118869300/118869279/05de4058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118870000/118869300/118869279/65834f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118870000/118869300/118869279/1a8c928b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![10 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/119000000/118870000/118869300/118869279/6e29adf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge Stony Point [](https://www.expedia.ca/Stony-Point-Hotels-Luxury-10BR-Escape-W-Pool.h118869279.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113610000/113603200/113603125/d28d79cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113610000/113603200/113603125/e8ace80f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113610000/113603200/113603125/91bdd53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/114000000/113610000/113603200/113603125/d745a3e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Retreat w/ Pool, Hot Tub & Game Room Stony Point 4.0/10 (1) "The house itself was fine but the pool was unusable and not maintained. We were frequently promised it would be fixed each day but there was no maintenance done. Even going through support, there was no attempt to make things right and we were unable to use the pool during a hot summer weekend. (There aren't even any pool towels for use)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin L. [](https://www.expedia.ca/Stony-Point-Hotels-Spacious-Retreat-W-Pool.h113603125.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/abd47b85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/77444f8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/w1896h1262x4y4-cfbd0bcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/31f65901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT Brewster 9.2/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) LaTisha B. CA $1,189 CA $2,190 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Brewster-Hotels-Upstate-Historical-Artist-Villa-W-Firepit.h101878310.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75820000/75814300/75814274/8033fecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75820000/75814300/75814274/857f4fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/76000000/75820000/75814300/75814274/a155f00d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75820000/75814300/75814274/907d7e4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 bedroom villa in bridgeport Bridgeport 9.8/10 Exceptional (8) "Great house. Perfect for visiting students at Sacred Heart. Only thing that would have made location better was the weather. Beautiful view I wish we could have enjoyed more. House was very high tec! We will definitely be back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine M. [](https://www.expedia.ca/Bridgeport-Hotels-Vrbo-Property.h75814274.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107830000/107826200/107826191/eadd18aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/108000000/107830000/107826200/107826191/0df11d05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/108000000/107830000/107826200/107826191/7512a663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107830000/107826200/107826191/0fd6b5a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Retreat with Autumn Views and Game Room Stony Point 10/10 Exceptional (3) "Stayed for 3 nights with friends and family had an absolute blast! Amazing house! 100% would book this house again. I highly recommend this house. Very clean and very comfortable. If you had any questions owner would get back to you very quickly. Overall 10/10 stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregg S. [](https://www.expedia.ca/Stony-Point-Hotels-5-Bdrm-Luxury-Near-West-Point-With-Gym.h107826191.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/112000000/111480000/111471200/111471114/1db73b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111480000/111471200/111471114/3b20b97f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111480000/111471200/111471114/f4044c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111480000/111471200/111471114/e89833ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hudson Valley Estate on 4 Acres w/ Private Pool! Nyack [](https://www.expedia.ca/Nyack-Hotels-Hudson-Valley-Estate-On-4-Acres-W-Private-Pool.h111471114.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/49000000/48760000/48754300/48754225/351f4f43_edited_671d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/49000000/48760000/48754300/48754225/cc1b8c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/49000000/48760000/48754300/48754225/0e28770b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/49000000/48760000/48754300/48754225/340300f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Castle 1876 13 Mins to Wing Foot cc border of GREENWICH and New York Rye Brook [](https://www.expedia.ca/White-Plains-Hotels-Historic-Castle-1876-13-Mins-To-Wing-Foot-Cc-Border-Of-Greenwich-And-New-York.h48754225.Hotel-Information) ![Villa](https://images.trvl-media.com/lodging/115000000/114320000/114311000/114310925/1415e71a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa](https://images.trvl-media.com/lodging/115000000/114320000/114311000/114310925/e3942d3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa](https://images.trvl-media.com/lodging/115000000/114320000/114311000/114310925/4892c54b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa](https://images.trvl-media.com/lodging/115000000/114320000/114311000/114310925/34f3e338.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Retreat With Autumn Views and Fireplace Stony Point [](https://www.expedia.ca/Stony-Point-Hotels-Luxury-5-Bdrm-Getaway-Near-West-Point.h114310925.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/109000000/108460000/108457500/108457494/w1170h778x0y21-c749911c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108460000/108457500/108457494/w1170h765x0y1-420694a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/109000000/108460000/108457500/108457494/w1170h800x0y11-79646726.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/109000000/108460000/108457500/108457494/w1170h777x0y16-fc127d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom villa in serene Holmes with AC, WiFi Holmes [](https://www.expedia.ca/Holmes-Hotels-Charming-2-Bedroom-Villa-In-Serene-Holmes-With-AC.h108457494.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120440000/120435300/120435279/d7399c79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120440000/120435300/120435279/9d4b6714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120440000/120435300/120435279/87d07d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120440000/120435300/120435279/0fdfa155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Storybook 330 Year Old Enchanting Estate Newtown [](https://www.expedia.ca/Newtown-Hotels-NEW-Storybook-330-Year-Old-Enchanting-Estate.h120435279.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=2025-11-15&endDate=2025-11-16®ionId=553248635976002127&adults=2&lodging=VILLA&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) 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-Villas.d553248635976002127-aaVillas.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Lewisboro-Villas.d553248635976002127-aaVillas.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 "." [](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 "staff was very helpful and the view was very nice" [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![The Circle Hotel Fairfield](//images.trvl-media.com/lodging/10000000/9820000/9816500/9816438/b1e811bb_y.jpg) ### The Circle Hotel Fairfield 10/10 Excellent "Easy check in process " [](https://expedia.ca/New-Haven-Hotels-The-Circle-Hotel-Fairfield.h9816438.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 "The staff was great. " [](https://expedia.ca/Stamford-Hotels-Norwalk-Inn.h15114.Hotel-Information) ![Baymont by Wyndham White Plains - Elmsford](//images.trvl-media.com/lodging/1000000/10000/500/438/w8985h6000x10y0-9d556f34_y.jpg) ### Baymont by Wyndham White Plains - Elmsford 10/10 Excellent "Room was excellent and my only complaint would be the outdated television and remote. Many channels were not available and also no info on any channels what you were watching " [](https://expedia.ca/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.Hotel-Information) ![The Armon Stamford Hotel & Conference](//images.trvl-media.com/lodging/90000000/89820000/89818900/89818854/99ae042b_y.jpg) ### The Armon Stamford Hotel & Conference 10/10 Excellent "Excellent! Will be glad to be back for sure!" [](https://expedia.ca/Stamford-Hotels-The-Armon-Hotel-Conference.h89818854.Hotel-Information) ![Amsterdam Hotel](//images.trvl-media.com/lodging/1000000/30000/20800/20793/f5bb9592_y.jpg) ### Amsterdam Hotel 10/10 Excellent "Very nice stay" [](https://expedia.ca/Stamford-Hotels-Amsterdam-Hotel.h20793.Hotel-Information) ![Tarrytown House Estate](//images.trvl-media.com/lodging/1000000/50000/49700/49674/a89a02a1_y.jpg) ### Tarrytown House Estate 10/10 Excellent "Great place " [](https://expedia.ca/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information) ![Hyatt Regency Greenwich](//images.trvl-media.com/lodging/1000000/20000/18200/18180/19d28016_y.jpg) ### Hyatt Regency Greenwich 10/10 Excellent "Beautiful hotel. Nice stay. Comfortable bed. Will come again. " [](https://expedia.ca/Stamford-Hotels-Hyatt-Regency-Greenwich.h18180.Hotel-Information) ## Find out more about Town of Lewisboro ## Town of Lewisboro Villas information | Number of reviews | 20 | | --- | --- | | Accommodation | 10 Villas | | Lowest Price | CA $2,190 | | Highest Price | CA $2,190 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [B&B in Bedford](https://www.expedia.ca/Bedford-Bed-And-Breakfast.d553248628384502029-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Castles in Bedford](https://www.expedia.ca/Bedford-Castles.d553248628384502029-aaCastles.Travel-Guide-Accommodation) - [Chalets in Bedford](https://www.expedia.ca/Bedford-Chalets.d553248628384502029-aaChalets.Travel-Guide-Accommodation) - [Aparthotels in Bedford Hills](https://www.expedia.ca/Bedford-Hills-Apart-Hotels.d3000448022-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Bedford Hills](https://www.expedia.ca/Bedford-Hills-Bed-And-Breakfast.d3000448022-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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