Title: Town of Lewisboro Vacation Home Rentals from CA $204: Search Top Private Vacation Homes for Rent | 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 # Town of Lewisboro Vacation Rentals ## 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 Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&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 ![Outdoor dining](https://images.trvl-media.com/lodging/95000000/94780000/94775200/94775128/618d1a43.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) ![Game room](https://images.trvl-media.com/lodging/95000000/94780000/94775200/94775128/3fd5c0ea.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. " [](https://www.expedia.ca/New-Fairfield-Hotels-Lakehouse-Boat-Dock.h94775128.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/7ce63cd7.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) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/115000000/114610000/114606200/114606188/71684fe5.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) ### 2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock. Greenwich 9.4/10 Exceptional (13) "Perfect place to rest. Excellent service! " CA $105 CA $277 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Greenwich-Hotels-2-Bedroom-And-1-Full-Bath-In-Lakeside-Home-With-Private-Dock.h114606188.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) ![Beach](https://images.trvl-media.com/lodging/72000000/71960000/71952400/71952323/5aa43ade.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) ### Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. Carmel Hamlet 10/10 Exceptional (90) "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. " [](https://www.expedia.ca/Carmel-Hotels-Lost-In-The-Woods.h71952323.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95740000/95733800/95733752/c0b8b1e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95740000/95733800/95733752/0fd4003b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/96000000/95740000/95733800/95733752/1e25c7a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95740000/95733800/95733752/785bf5ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc! New Fairfield 8.8/10 Excellent (23) "We were very happy with the accommodations. The cottage was neat, clean and well kept, as was the property. All the amenities were as described. We had a great weekend and would highly recommend this lake house." [](https://www.expedia.ca/New-Fairfield-Hotels-Lakehouse-Cottage-W-Boat-Dock-Kayaks-1-Hour-15-Min-From-NYC-On-Squantz-Pond.h95733752.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111840000/111840000/111839951/4056a1d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/112000000/111840000/111840000/111839951/949e7ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/112000000/111840000/111840000/111839951/81c44254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111840000/111840000/111839951/7dcc0b14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stareway to Heaven Su Fairfield 10/10 Exceptional (10) "Beautiful house that offered tremendous comfort and amenities, all modern. " [](https://www.expedia.ca/Fairfield-Hotels-Stareway-To-Heaven-Su.h111839951.Hotel-Information) ![Children's area](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/19ba220c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/30bbd2c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/13a74fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/1c1ed8a9.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" CA $592 CA $851 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Fishkill-Hotels-Hickory-On-Willow-Lake.h112586795.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89810000/89804200/89804199/w2834h1890x2y0-f8c3ab8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/90000000/89810000/89804200/89804199/w2833h1887x3y3-ea70202b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89804200/89804199/w2832h1886x4y3-17cc3841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89804200/89804199/w2840h1886x0y3-b48fa6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeview Estate - Chef's Kitchen - NYC Getaway Danbury 9.8/10 Exceptional (30) "Happy to have rebooked!!" [](https://www.expedia.ca/Danbury-Hotels-Lakefront-Estate-Relaxed-Luxury-NYC-Getaway.h89804199.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/120000000/119110000/119104400/119104338/0d0a14be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119110000/119104400/119104338/5dcacc61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/120000000/119110000/119104400/119104338/5ff351ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119110000/119104400/119104338/b33ebc97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Friendly, Modern and Spacious 5-bedroom house in marvelous Westport, CT! Westport 10/10 Exceptional (2) "We had an amazing trip in this beautiful home! Would definitely return without hesitation! " [](https://www.expedia.ca/Westport-Hotels-Family-Friendly.h119104338.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) ![Private kitchen](https://images.trvl-media.com/lodging/113000000/112370000/112364900/112364813/bdaff4ee.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) ### Charming 2-bedroom house in fabulous Stamford with AC, WiFi Waterside 10/10 Exceptional (4) "Lovely little home in Stamford." CA $244 CA $494 total includes taxes & fees Oct 1 - Oct 2 [](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/116000000/115350000/115345700/115345699/74e2f6c0.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) ### Spacious 4-bedroom house in charming Rye with AC Rye CA $279 CA $634 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Rye-Hotels-Spacious-4-Bedroom-House-In-Charming-Rye-With-AC.h115345699.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) ![Exterior](https://images.trvl-media.com/lodging/98000000/97480000/97470900/97470860/9ac447c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/98000000/97480000/97470900/97470860/646e6d85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Business or Weekend escape Stratford 9.2/10 Wonderful (46) "We had stayed at Mansoor's a few weeks ago and returned this past weekend. Once again, we found the place spotless, comfortable and well-stocked. We really like this place and expect to return again in the future. " CA $118 CA $204 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Stratford-Hotels-Business-Or-Weekend-Escape.h97470860.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) ![4 bedrooms, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/97000000/96850000/96842000/96841918/45c2db90.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." [](https://www.expedia.ca/Nyack-Hotels-Castle-In-The-Sky-Beautifully-Renovated-Victorian-One-Block-From-Main-St.h96841918.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117740000/117735700/117735656/25132749_edited_9c19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/118000000/117740000/117735700/117735656/cfdd2318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117740000/117735700/117735656/0ec0c0ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/118000000/117740000/117735700/117735656/40849652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Soothing Carriage House with Hot Tub in charming Stratford Stratford 10/10 Exceptional (5) [](https://www.expedia.ca/Stratford-Hotels-Soothing-Carriage-House-With-Hot-Tub-In-Charming-Stratford.h117735656.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78690000/78689500/78689411/cd25c824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78690000/78689500/78689411/89e53b55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78690000/78689500/78689411/64cea77c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/79000000/78690000/78689500/78689411/be217384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views! Danbury 10/10 Exceptional (47) "We really enjoyed totally this Candlewood lake house. it has a fantastic view and a large, beautiful lawn with a fire pit. The owner was a pleasure to work with and she even allowed us to check in a few hours early.The house is fully stocked with everything we needed. The views are fabulous, but if you bring your own boat, the property is at the tip of the lake and the water can be a little rough from other boats going by. " [](https://www.expedia.ca/Danbury-Hotels-Candlewood-Lakefront-3bd-2-Bath-House-W-180-Degree-Views.h78689411.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/93000000/92320000/92311600/92311588/f446d572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92320000/92311600/92311588/9f5004fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92320000/92311600/92311588/c001f523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92320000/92311600/92311588/fade400f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT New Milford 10/10 Exceptional (13) "Beautiful location and lots of space for a large group. This rental is really about the outdoor space and activities. Would love to return!" [](https://www.expedia.ca/New-Milford-Hotels-Lands-End-Direct-Lake-Front-On-Warner-Point.h92311588.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) ![Pool](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/490a9125.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) ### Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! Ossining 8.6/10 Excellent (4) "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. " CA $644 CA $1,312 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Ossining-Hotels-Castle-Cozy-Winter-Wonderland-Events.h101852343.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102350000/102342400/102342378/w1179h783x0y2-92eb770e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102350000/102342400/102342378/w1179h772x0y0-e4878f72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/103000000/102350000/102342400/102342378/5bb48ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102350000/102342400/102342378/w1179h783x0y0-6faa5ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon. Carmel Hamlet 10/10 Exceptional (17) "We had a great stay and had everything we needed!" CA $626 CA $1,207 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Carmel-Hotels-Beautiful-Escape-Hudson-Valley-LakeHouse-90min-From-NYC-30min-From-Beacon.h102342378.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117680000/117670700/117670643/cf723149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/118000000/117680000/117670700/117670643/w1020h679x4y4-1952ce42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117680000/117670700/117670643/10e384fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/118000000/117680000/117670700/117670643/22afb54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Luxury Home – Peaceful, Comfortable, and Fully Private. Mount Kisco 2.0/10 (1) "The property is lovely and the home spacious. Unfortunately we found the home not to be maintained well or properly cleaned. There was significant mold in the master bath shower, dirty and torn upholstery, stained sheets and rugs, dirty pots and pans, dirty shelves, holes in walls, hanging fixtures, dirty bug filled window sills, loose faucets, non working tub sprayer, dirty outdoor furniture and many more issues. When we voiced concerns to the host we were told to vacate immediately and had no... [](https://www.expedia.ca/Mount-Kisco-Hotels-Secluded-Luxury-Home-Peaceful.h117670643.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/112000000/111350000/111342400/111342347/dd31fdd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/112000000/111350000/111342400/111342347/59c64f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/112000000/111350000/111342400/111342347/74b6cf94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/112000000/111350000/111342400/111342347/a358b110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom house in Bridgeport.Trumbull/Fairfield line with AC, WiFi. Bridgeport 10/10 Exceptional (2) "Good experience" [](https://www.expedia.ca/Bridgeport-Hotels-Charming-2-Bedroom-House-In-BridgeportTrumbullFairfield-Line-With-AC.h111342347.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/105000000/104070000/104069800/104069775/b4803f41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104070000/104069800/104069775/7b17bd48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/105000000/104070000/104069800/104069775/535a3b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/105000000/104070000/104069800/104069775/a1cc43b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW Candlewood Lake 3BR 2BA Direct Waterfront Home~ Dock~Fire Pit~Sunset Views! Brookfield 10/10 Exceptional (13) "House and property are beautiful. Everything was great!" [](https://www.expedia.ca/Brookfield-Hotels-Gorgeous-NEW-Candlewood-Lake-4BR-2BA-Direct-Waterfront-Home-Private-Dock-Patio.h104069775.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=2025-10-13&endDate=2025-10-14®ionId=553248635976002127&adults=2&lodging=VACATION_HOME&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-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 ![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) ![Sonesta White Plains Downtown](//images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg) ### Sonesta White Plains Downtown 10/10 Excellent "Clean room and friendly staff" [](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.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) ![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 "Wonderful staff!" [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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) ## Find out more about Town of Lewisboro ## Town of Lewisboro Vacation Homes information | Number of reviews | 349 | | --- | --- | | Accommodation | 437 Vacation Homes | | Lowest Price | CA $204 | | Highest Price | CA $1,312 | ## 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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