Title: Town of Lewisboro Cottages from CA $429 | 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 Cottage Rentals from CA $429 ## 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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Featured Cottages in Town of Lewisboro ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/5ed95c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/67801e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/e56d490f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands Fort Montgomery 9.8/10 Exceptional (124) "It has an incredible mountain and water view. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MIHYUN CA $262 CA $429 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/116000000/115140000/115131900/115131896/b74b1e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/116000000/115140000/115131900/115131896/60db8f65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/116000000/115140000/115131900/115131896/6b06b203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/116000000/115140000/115131900/115131896/9242892b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven Croton-on-Hudson 9.6/10 Exceptional (14) "Lovely two weeks in the carriage house on the Croton River. Hosts Patrick and Kathryn were attentive and helpful, the area was full of fun adventures for my husband, a cyclist, and me (jogger and kayaker). Swimming in the Croton from the dock was so great, especially on warm days. Kayaking in the Croton was peaceful and full of fun water birds." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann M. [](https://www.expedia.ca/Croton-On-Hudson-Hotels-Romantic-Retreat-With-Stunning-Views-Of-Croton-River-Gorge.h115131896.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109920000/109918200/109918168/8998ceb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/110000000/109920000/109918200/109918168/c87a82fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/110000000/109920000/109918200/109918168/593e61e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/110000000/109920000/109918200/109918168/dce53716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cos Cob Cottage- Full Kitchen, Pet Friendly Greenwich 10/10 Exceptional (4) "2 night stay over Thanksgiving holiday. Cozy Cottage was just lovely. Fully applianced and stocked kitchen. Large bathroom-super soft towels. King size bed was comfy and cozy. Living room was perfect for relaxing. Rules clearly communicated. Owners were very helpful and responsive. Driveway a little tricky to maneuver when parking spots are occupied. Safe location…. Good walking and exploring in the area " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Teresa F. [](https://www.expedia.ca/Cos-Cob-Hotels-Cos-Cob-Cottage-Full-Kitchen.h109918168.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103820000/103816700/103816658/1330fc7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103820000/103816700/103816658/9fe95b3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103820000/103816700/103816658/5fabeac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103820000/103816700/103816658/f468b550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break? Weston 10/10 Exceptional (11) "Wonderful stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) james v. [](https://www.expedia.ca/Weston-Hotels-Escape-To-River-Cottage-Ready-For-Hiking.h103816658.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186905/339d07ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186905/6a506072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186905/01a73673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186905/788e0bff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT Bethel 10/10 Exceptional (8) "Great relaxing stay quite and comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ken G. [](https://www.expedia.ca/Bethel-Hotels-Charming-1-Bedroom-Cottage-With-WiFi-And-AC-In-Enchanting-Bethel.h107186905.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106090000/106082800/106082742/0c99c9bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106090000/106082800/106082742/fa2cef8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106090000/106082800/106082742/1f260241.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106090000/106082800/106082742/46e54403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magnificent Lake View Holmes [](https://www.expedia.ca/Holmes-Hotels-Magnificent-Lake-View.h106082742.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812263/562b2376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812263/17927bbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812263/6c8e306a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812263/2b01da43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westport "Gold Coast" across from Southport beach Fairfield 10/10 Exceptional (95) "Easy communication, clean apartment, good location for beach and nearby towns. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn D. [](https://www.expedia.ca/Stamford-Hotels-Westport-Gold-Coast-Across-From-Southport-Beach.h19812263.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118950000/118948200/118948200/8efdb114.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118950000/118948200/118948200/cf4d6b78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118950000/118948200/118948200/fde62a1b.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/119000000/118950000/118948200/118948200/ab8c4a00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Studio-Cottage with WiFi & TV free parking in Greenwich Greenwich [](https://www.expedia.ca/Cos-Cob-Hotels-Charming-Studio-Cottage-With-WiFi-TV-Free-Parking-In-Greenwich.h118948200.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/75000000/74650000/74640700/74640684/d32bbef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74650000/74640700/74640684/8b139310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74650000/74640700/74640684/431e8c30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74650000/74640700/74640684/dee1f81b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trendy 1 bedroom +loft apartment w/ parking West Side 10/10 Exceptional (12) "Perfect for my needs. Would stay again for sure" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael M. [](https://www.expedia.ca/Stamford-Hotels-Trendy-1-Bedroom-Loft-Apartment-W-Parking.h74640684.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118260000/118254600/118254559/2bf56582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118260000/118254600/118254559/d9ad9954.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118260000/118254600/118254559/36e641f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118260000/118254600/118254559/33b51e52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy cottage in charming Pound Ridge with WiFi, AC Pound Ridge [](https://www.expedia.ca/Pound-Ridge-Hotels-Cozy-Cottage-In-Charming-Pound-Ridge-With-WiFi.h118254559.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94380000/94370800/94370734/89000325.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94380000/94370800/94370734/c0e5b79f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94380000/94370800/94370734/8c6b2288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94380000/94370800/94370734/8ba2ef19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Updated Home w/ Patio Half Mile to West Point Highland Falls [](https://www.expedia.ca/Highland-Falls-Hotels-Updated-Home-W-Patio-Half-Mile-To-West-Point.h94370734.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/e74463e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/2ca37619.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/1c766ca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/0f1e7af8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage with Grill | Walk to Lake Putnam Valley 9.8/10 Exceptional (22) "Our second time staying at the cottage and we love it so much. So comfortable. So close to the lake, and just fabulous!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CarlyS CA $269 CA $702 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Putnam-Valley-Hotels-Cottage-Getaway-DogFriendly.h91391396.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108730000/108722100/108722014/46b6c1ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108730000/108722100/108722014/af650ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108730000/108722100/108722014/67bef6ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108730000/108722100/108722014/c41aec29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly! New Canaan 10/10 Exceptional (3) "We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) danyelle s. [](https://www.expedia.ca/New-Canaan-Hotels-Charming-2-BdRm-Cottage-In-Peaceful-New-Canaan.h108722014.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105550000/105549800/105549790/23bf9aa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105550000/105549800/105549790/6f24a430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105550000/105549800/105549790/0b85872b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105550000/105549800/105549790/008285de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Highland Falls Home < 2 Mi to West Point! Highland Falls 10/10 Exceptional (1) "Fabulous place - great for our family weekend at West Point. Plenty of room, lovely kitchen, and lots of seating - whole group of us could watch the baseball playoffs. Terrific - not a single problem or complaint!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mia [](https://www.expedia.ca/Highland-Falls-Hotels-Charming-Highland-Falls-Home-2-Mi-To-West-Point.h105549790.Hotel-Information) ![Cottage (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/110000000/109810000/109808300/109808229/6044cee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/110000000/109810000/109808300/109808229/7a05e71a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/110000000/109810000/109808300/109808229/fccc30b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/110000000/109810000/109808300/109808229/328c78ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene Holmes Cottage Near Lakes & Trails! Holmes [](https://www.expedia.ca/Holmes-Hotels-Serene-Holmes-Cottage-Near-Lakes-Trails.h109808229.Hotel-Information) ![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98550500/98550476/6050b244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98550500/98550476/a50bc069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98550500/98550476/1f5d6850.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/99000000/98560000/98550500/98550476/4d825089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakefront Brewster Vacation Rental w/ Private Dock Brewster [](https://www.expedia.ca/Brewster-Hotels-Lakefront-Brewster-Vacation-Rental-W-Private-Dock.h98550476.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119120000/119110700/119110669/39964620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119120000/119110700/119110669/08835df3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119120000/119110700/119110669/366c2871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119120000/119110700/119110669/fa5494e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Squantz Pond Oasis, charming cottage, Firepit and lake view New Fairfield [](https://www.expedia.ca/New-Fairfield-Hotels-Squantz-Pond-Oasis.h119110669.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/103000000/102410000/102402600/102402574/54357bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (1 Bedroom) | Living area](https://images.trvl-media.com/lodging/103000000/102410000/102402600/102402574/03f0e572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102410000/102402600/102402574/c0f5dba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102410000/102402600/102402574/d4f1fc35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dreamy Hudson Valley Cottage w/ State Park Views Garrison 10/10 Exceptional (1) "The house was amazing with great amenities. The kitchen was stocked with all the utensils and cutlery. The patio was a good addition. Overall great stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Santhosh [](https://www.expedia.ca/Garrison-Hotels-Dreamy-Hudson-Valley-Cottage-W-State-Park-Views.h102402574.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33660000/33654500/33654427/ab023d08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33660000/33654500/33654427/ff9add5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33660000/33654500/33654427/e6022470.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33660000/33654500/33654427/5748f882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachfront cottage located in the heart of Fairfield Beach!! Fairfield 9.6/10 Exceptional (18) "I grew up here! Always fun" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John C. [](https://www.expedia.ca/New-Haven-Hotels-Waterfrontbeachfront-Cottage-Located-In-The-Heart-Of-Fairfield-Beach.h33654427.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90700000/90694500/90694498/42c33e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90700000/90694500/90694498/c2e1f3e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90700000/90694500/90694498/4573b840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90700000/90694500/90694498/ed321974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Second floor cottage apartment located in a private community. Cove - East Side - Shippan 9.6/10 Exceptional (17) "Great time, nice little private neighborhood! Pretty views if you go for nice walks. 2 great parks near by. Lovely stay. Had everything we needed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel M. [](https://www.expedia.ca/Stamford-Hotels-Second-Floor-Cottage-Apartment-Located-In-A-Private-Community.h90694498.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=2025-11-14&endDate=2025-11-15®ionId=553248635976002127&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Cottages.d553248635976002127-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Lewisboro-Cottages.d553248635976002127-aaCottages.Travel-Guide-Accommodation) ## Top Town of Lewisboro Hotel Reviews ![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) ![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 "The room was clean and well maintained. The only problem was that the fan in the bathroom came on when the light was turned on which made it noisy. It may have been hooked in wrong because there was a switch next to it but it didn’t do anything when it was turned on. " [](https://expedia.ca/Danbury-Hotels-Microtel-Inn-Suites-By-Wyndham-BethelDanbury.h579216.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 "No complaints at all" [](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![HYATT house White Plains](//images.trvl-media.com/lodging/1000000/430000/427300/427283/458cd7c2_y.jpg) ### HYATT house White Plains 10/10 Excellent "Felt safe " [](https://expedia.ca/White-Plains-Hotels-HYATT-House-White-Plains.h427283.Hotel-Information) ![The Stamford Hotel](//images.trvl-media.com/lodging/1000000/50000/42300/42258/d312d428_y.jpg) ### The Stamford Hotel 10/10 Excellent "Very nice " [](https://expedia.ca/Stamford-Hotels-The-Stamford-Hotel.h42258.Hotel-Information) ## Find out more about Town of Lewisboro ## Town of Lewisboro Cottages information | Number of reviews | 296 | | --- | --- | | Accommodation | 72 Cottages | | Lowest Price | CA $429 | | Highest Price | CA $702 | ## Explore a world of travel with Expedia - 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[Brewster Vacation Rentals](https://www.expedia.ca/Brewster-Vacation-Rentals.d183644.Travel-Guide-VacationRentals) - [Katonah Vacation Rentals](https://www.expedia.ca/Katonah-Vacation-Rentals.d505584.Travel-Guide-VacationRentals) - [Things to do in Bedford](https://www.expedia.ca/Things-To-Do-In-Bedford.d553248628384502029.Travel-Guide-Activities) - [Things to do in Brewster](https://www.expedia.ca/Things-To-Do-In-Brewster.d183644.Travel-Guide-Activities) - [Book Cottages in Town of Lewisboro on Expedia.com](https://www.expedia.com/Town-Of-Lewisboro-Cottages.d553248635976002127-aaCottages.Travel-Guide-Accommodation)