Title: Town of Lewisboro Cottages from CA $430 | 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 $430 ## 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 [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=COTTAGE&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&lodging=COTTAGE&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&lodging=COTTAGE&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&lodging=COTTAGE&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-Cottages.d3000448270-aaCottages.Travel-Guide-Accommodation) ## 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) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/dfec5e09.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) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/67801e28.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 (123) "It has an incredible mountain and water view. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MIHYUN CA $263 CA $430 total includes taxes & fees Oct 28 - Oct 29 [](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) ![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) ![Private kitchen](https://images.trvl-media.com/lodging/116000000/115140000/115131900/115131896/60db8f65.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 9.8/10 Exceptional (12) "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) ![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) ![TV](https://images.trvl-media.com/lodging/110000000/109920000/109918200/109918168/6c5e684d.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/104000000/103820000/103816700/103816658/3a952091.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) ![Interior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186905/788e0bff.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) ![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) ### 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) ![Dining](https://images.trvl-media.com/lodging/107000000/106090000/106082800/106082742/46e54403.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) ![Interior](https://images.trvl-media.com/lodging/107000000/106090000/106082800/106082742/16d10761.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812263/17927bbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812263/3c2b6fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westport "Gold Coast" across from Southport beach Fairfield 10/10 Exceptional (94) "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) ![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) ![Interior](https://images.trvl-media.com/lodging/119000000/118950000/118948200/118948200/71887b3b.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/dee1f81b.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) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/75000000/74650000/74640700/74640684/6a03f4ac.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) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/119000000/118260000/118254600/118254559/4aa35d7a.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) ![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) ### 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/fd5ddc2d.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) ### 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) ![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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/08a3846a.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 $705 total includes taxes & fees Oct 27 - Oct 28 [](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) ![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) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108730000/108722100/108722014/357e067e.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) ### 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/106000000/105550000/105549800/105549790/008285de.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/106000000/105550000/105549800/105549790/537830fb.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/fccc30b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/110000000/109810000/109808300/109808229/7a05e71a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/110000000/109810000/109808300/109808229/4dbd7cdc.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/99000000/98560000/98550500/98550476/1f5d6850.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/d8967df6.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) ### 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) ![Interior](https://images.trvl-media.com/lodging/120000000/119120000/119110700/119110669/66fa86e5.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) ### 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) ![Interior](https://images.trvl-media.com/lodging/103000000/102410000/102402600/102402574/d4f1fc35.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) ![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) ### 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) ![Interior](https://images.trvl-media.com/lodging/34000000/33660000/33654500/33654427/e6022470.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) ![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) ![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) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90700000/90694500/90694498/132bb8fa.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=2025-11-08&endDate=2025-11-09®ionId=553248635976002127&adults=2&lodging=COTTAGE&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-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 ![Westchester Marriott](//images.trvl-media.com/lodging/1000000/20000/10900/10829/w3995h2667x0y0-3f6e8d0f_y.jpg) ### Westchester Marriott 10/10 Excellent "Great staff especially Rose at the front desk " [](https://expedia.ca/Tarrytown-Hotels-Westchester-Marriott.h10829.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) ![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) ![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 "It was grear for the time i stayed." [](https://expedia.ca/Stamford-Hotels-The-Armon-Hotel-Conference.h89818854.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 "Decent great price " [](https://expedia.ca/Nyack-Hotels-West-Gate-Inn-Nyack.h5843352.Hotel-Information) ## Find out more about Town of Lewisboro ## Town of Lewisboro Cottages information | Number of reviews | 293 | | --- | --- | | Accommodation | 72 Cottages | | Lowest Price | CA $430 | | Highest Price | CA $705 | ## 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) - 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