Title: Town of Lewisboro Villas from CA $1,260 | 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 $1,260 ## Compare and save ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Featured Villas in Town of Lewisboro ![Exterior](https://images.trvl-media.com/lodging/119000000/118870000/118869300/118869279/05de4058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118870000/118869300/118869279/bffdf7f9.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) ![Exterior](https://images.trvl-media.com/lodging/119000000/118870000/118869300/118869279/65834f2a.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) ![Living area](https://images.trvl-media.com/lodging/114000000/113610000/113603200/113603125/d745a3e2.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) ![Private kitchen](https://images.trvl-media.com/lodging/114000000/113610000/113603200/113603125/84a1c5b0.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)" [](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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/77444f8f.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) "Property was exactly what we were looking for with a group as large as ours (14 people). Plenty of indoor and outdoor space. Great kitchen as well (cooked all of our meals in the house for the whole group)." CA $1,184 CA $2,063 total includes taxes & fees Oct 13 - Oct 14 [](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) ![Sport court](https://images.trvl-media.com/lodging/76000000/75820000/75814300/75814274/a155f00d.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) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75820000/75814300/75814274/aa42b2e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 bedroom villa in bridgeport Bridgeport 9.8/10 Exceptional (8) "This was a great house. Very clean, centrally located right on the lake. I enjoyed my weekend there. I definitely will book this again" [](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) ![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) ![Interior](https://images.trvl-media.com/lodging/108000000/107830000/107826200/107826191/9d428ffc.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) ### 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!" [](https://www.expedia.ca/Stony-Point-Hotels-5-Bdrm-Luxury-Near-West-Point-With-Gym.h107826191.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119730000/119724400/119724381/c5ab9006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119730000/119724400/119724381/f970a650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/120000000/119730000/119724400/119724381/cb7ba131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/120000000/119730000/119724400/119724381/ebcfc23f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 7BD Mention Celebration Welcomes Norwalk 10/10 Exceptional (1) "I had a wonderful stay at this house. It was very clean, comfortable, and beautifully maintained.Everything was exactly as described, and I really appreciated the welcoming atmosphere. Even though I only stayed for one day, it was an amazing experience. I would definitely recommend this place and would love to stay again in the future." CA $836 CA $1,260 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Norwalk-Hotels-Spacious-7-Bedroom-House-In-Delightful-Norwalk-With-AC.h119724381.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/d7b8b432.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) ![Interior](https://images.trvl-media.com/lodging/112000000/111480000/111471200/111471114/3b20b97f.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) ![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/w3000h2168x0y0-977f5e01.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/115000000/114320000/114311000/114310925/34f3e338.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) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108460000/108457500/108457494/w1170h775x0y0-956d3b61.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) ### 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/49000000/48760000/48754300/48754225/351f4f43_edited_671d.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) ![Interior](https://images.trvl-media.com/lodging/49000000/48760000/48754300/48754225/w1440h962x0y0-5a36ee0c.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) ### 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) ![Exterior](https://images.trvl-media.com/lodging/121000000/120440000/120435300/120435279/d7399c79.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) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120440000/120435300/120435279/9d4b6714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/121000000/120440000/120435300/120435279/aae5b383.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=2025-10-12&endDate=2025-10-13®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 ![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 "Facility wax clean and quiet. We were visiting our daughter in college. Very Disappointing the facility offered not food, especially coffee on location. " [](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 "N/A. Wi-Fi was adequate. " [](https://expedia.ca/Stamford-Hotels-Amsterdam-Hotel.h20793.Hotel-Information) ![Trumbull Marriott Shelton](//images.trvl-media.com/lodging/1000000/10000/1200/1166/b3c487eb_y.jpg) ### Trumbull Marriott Shelton 10/10 Excellent "The best" [](https://expedia.ca/New-Haven-Hotels-Trumbull-Marriott-Shelton.h1166.Hotel-Information) ![Tarrytown House Estate](//images.trvl-media.com/lodging/1000000/50000/49700/49674/a89a02a1_y.jpg) ### Tarrytown House Estate 10/10 Excellent "Room was awesome and staff was very courteous " [](https://expedia.ca/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.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 "Short stay however. The Front desk was very nice. Clean hotel at a fair price. Happy overall." [](https://expedia.ca/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.Hotel-Information) ![EVEN Hotel Norwalk by IHG](//images.trvl-media.com/lodging/1000000/10000/2600/2584/4cb7d7eb_y.jpg) ### EVEN Hotel Norwalk by IHG 10/10 Excellent "Excellent service" [](https://expedia.ca/Stamford-Hotels-EVEN-Hotel-Norwalk.h2584.Hotel-Information) ![Microtel Inn & Suites by Wyndham Bethel/Danbury](//images.trvl-media.com/lodging/1000000/580000/579300/579216/ef7dd368_y.jpg) ### Microtel Inn & Suites by Wyndham Bethel/Danbury 10/10 Excellent "Excellent service" [](https://expedia.ca/Danbury-Hotels-Microtel-Inn-Suites-By-Wyndham-BethelDanbury.h579216.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 "Staff at the front desk and restaurant were thoughtful and responsive. The hotel and room were beautifully designed. The decor made it feel very much like a boutique hotel. Thanks!" [](https://expedia.ca/Nyack-Hotels-Hotel-Nyack.h11943081.Hotel-Information) ![West Gate Inn Nyack](//images.trvl-media.com/lodging/6000000/5850000/5843400/5843352/393dcf26_y.jpg) ### West Gate Inn Nyack 10/10 Excellent "This place basic but super clean and comfortable. The welcome was warm and I’m actually excited to try the hot breakfast buffet in the morning! I have a feeling it’s going to be pretty great. Easy highway access, plenty of stuff around including a c-store across the street. Taco Boys is a fantastic neighborhood spot up the street definitely worth a try. Loved it!!" [](https://expedia.ca/Nyack-Hotels-West-Gate-Inn-Nyack.h5843352.Hotel-Information) ## Find out more about Town of Lewisboro ## Town of Lewisboro Villas information | Number of reviews | 17 | | --- | --- | | Accommodation | 10 Villas | | Lowest Price | CA $1,260 | | Highest Price | CA $2,063 | ## 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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