Title: Town of Lewisboro Cottages from CA $419 | 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) ![Great spot for hiking, picnicking and camping. Lots of great trails in the woods and through the fields. Dog friendly. ](https://images.trvl-media.com/place/3000448270/a6652d18-8c91-4d4e-9b86-bd66ddf0fd56.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Marina Timo # Search Town of Lewisboro Cottage Rentals from CA $419 ## 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 In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976002127&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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) ## Our top choices for Town of Lewisboro cottages ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.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) ![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/5ed95c10.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 [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) Fort Montgomery 9.8/10 Exceptional (129) "It has an incredible mountain and water view. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MIHYUN CA $259 CA $419 total includes taxes & fees Dec 30 - Dec 31 [](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) ![Private kitchen](https://images.trvl-media.com/lodging/116000000/115140000/115131900/115131896/60db8f65.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) ### Eaglefest time! Plus stunning winter views of Croton River Gorge, a birder haven [](https://www.expedia.ca/Croton-On-Hudson-Hotels-Romantic-Retreat-With-Stunning-Views-Of-Croton-River-Gorge.h115131896.Hotel-Information) Croton-on-Hudson 9.6/10 Exceptional (15) "We enjoyed our overnight stay at this quaint nicely appointed carriage house." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cathleen C. [](https://www.expedia.ca/Croton-On-Hudson-Hotels-Romantic-Retreat-With-Stunning-Views-Of-Croton-River-Gorge.h115131896.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/75000000/74650000/74640700/74640684/431e8c30.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) ![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 [](https://www.expedia.ca/Stamford-Hotels-Trendy-1-Bedroom-Loft-Apartment-W-Parking.h74640684.Hotel-Information) West Side 9.6/10 Exceptional (14) "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) ![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92080000/92078200/92078116/cb715e6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92080000/92078200/92078116/ecec8b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/93000000/92080000/92078200/92078116/992325ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/93000000/92080000/92078200/92078116/82000bea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Retreat w/ Pool, Cinema Room & Fire Pit [](https://www.expedia.ca/Lake-Peekskill-Hotels-Cozy-Retreat-W-Pool.h92078116.Hotel-Information) Putnam Valley 9.6/10 Exceptional (14) "The property was amazing, Ceren was very accommodative, and we had a great time!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mohit B. CA $303 CA $903 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Lake-Peekskill-Hotels-Cozy-Retreat-W-Pool.h92078116.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) ![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/104000000/103820000/103816700/103816658/9fe95b3a.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) ### Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break? [](https://www.expedia.ca/Weston-Hotels-Escape-To-River-Cottage-Ready-For-Hiking.h103816658.Hotel-Information) Weston 10/10 Exceptional (12) "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) ![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/110000000/109920000/109918200/109918168/6c5e684d.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 [](https://www.expedia.ca/Cos-Cob-Hotels-Cos-Cob-Cottage-Full-Kitchen.h109918168.Hotel-Information) Greenwich 9.6/10 Exceptional (5) "Great Property. Driveway parking a bit of a challenge" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janet L. [](https://www.expedia.ca/Cos-Cob-Hotels-Cos-Cob-Cottage-Full-Kitchen.h109918168.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156092/b63e67bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156092/466d741b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156092/aafd38af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/25000000/24160000/24156100/24156092/85b8a586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Fairfield Beach 3BR 2BA Cottage By The Sea [](https://www.expedia.ca/Fairfield-Hotels-Charming-Cottage-By-The-Sea-On-Fairfield-Beach.h24156092.Hotel-Information) Fairfield Beach 10/10 Exceptional (33) "Overall a very smooth and enjoyable experience. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dora M. [](https://www.expedia.ca/Fairfield-Hotels-Charming-Cottage-By-The-Sea-On-Fairfield-Beach.h24156092.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) ![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) ![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 [](https://www.expedia.ca/Bethel-Hotels-Charming-1-Bedroom-Cottage-With-WiFi-And-AC-In-Enchanting-Bethel.h107186905.Hotel-Information) 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) ![Exterior](https://images.trvl-media.com/lodging/122000000/121360000/121354700/121354656/9c6fef46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121360000/121354700/121354656/0bee9204.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/122000000/121360000/121354700/121354656/36688c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121360000/121354700/121354656/w1320h879x0y0-56dadff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City [](https://www.expedia.ca/Greenwich-Hotels-Riverfront-Cottage-Heated-Pool-Hot-Tub-Fireplace-35minutes-From-New-York-City.h121354656.Hotel-Information) Greenwich CA $656 CA $1,366 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Greenwich-Hotels-Riverfront-Cottage-Heated-Pool-Hot-Tub-Fireplace-35minutes-From-New-York-City.h121354656.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) ![Interior](https://images.trvl-media.com/lodging/107000000/106090000/106082800/106082742/16d10761.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) ### Magnificent Lake View [](https://www.expedia.ca/Holmes-Hotels-Magnificent-Lake-View.h106082742.Hotel-Information) Holmes [](https://www.expedia.ca/Holmes-Hotels-Magnificent-Lake-View.h106082742.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/119000000/118950000/118948200/118948200/71887b3b.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) ![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 [](https://www.expedia.ca/Cos-Cob-Hotels-Charming-Studio-Cottage-With-WiFi-TV-Free-Parking-In-Greenwich.h118948200.Hotel-Information) Greenwich [](https://www.expedia.ca/Cos-Cob-Hotels-Charming-Studio-Cottage-With-WiFi-TV-Free-Parking-In-Greenwich.h118948200.Hotel-Information) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111760000/111759500/111759450/ad6c10a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111760000/111759500/111759450/877ec6b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111760000/111759500/111759450/32eb1608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/112000000/111760000/111759500/111759450/0a9033df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Mi to Downtown: Spacious White Plains Home [](https://www.expedia.ca/White-Plains-Hotels-3-Mi-To-Downtown-Spacious-White-Plains-Home.h111759450.Hotel-Information) White Plains [](https://www.expedia.ca/White-Plains-Hotels-3-Mi-To-Downtown-Spacious-White-Plains-Home.h111759450.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) ![Interior](https://images.trvl-media.com/lodging/20000000/19820000/19812300/19812263/3c2b6fe6.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 [](https://www.expedia.ca/Stamford-Hotels-Westport-Gold-Coast-Across-From-Southport-Beach.h19812263.Hotel-Information) Fairfield 10/10 Exceptional (97) "Excellent stay and value. I hope to return. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric B. [](https://www.expedia.ca/Stamford-Hotels-Westport-Gold-Coast-Across-From-Southport-Beach.h19812263.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) ![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) ![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) ![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) ### Cozy cottage in charming Pound Ridge with WiFi, AC [](https://www.expedia.ca/Pound-Ridge-Hotels-Cozy-Cottage-In-Charming-Pound-Ridge-With-WiFi.h118254559.Hotel-Information) Pound Ridge [](https://www.expedia.ca/Pound-Ridge-Hotels-Cozy-Cottage-In-Charming-Pound-Ridge-With-WiFi.h118254559.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/110000000/109810000/109808300/109808229/328c78ad.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) ### Serene Holmes Cottage Near Lakes & Trails! [](https://www.expedia.ca/Holmes-Hotels-Serene-Holmes-Cottage-Near-Lakes-Trails.h109808229.Hotel-Information) Holmes [](https://www.expedia.ca/Holmes-Hotels-Serene-Holmes-Cottage-Near-Lakes-Trails.h109808229.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119120000/119110700/119110669/08835df3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Squantz Pond Oasis, charming cottage, Firepit and lake view [](https://www.expedia.ca/New-Fairfield-Hotels-Squantz-Pond-Oasis.h119110669.Hotel-Information) New Fairfield [](https://www.expedia.ca/New-Fairfield-Hotels-Squantz-Pond-Oasis.h119110669.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/95000000/94380000/94370800/94370734/8ba2ef19.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 [](https://www.expedia.ca/Highland-Falls-Hotels-Updated-Home-W-Patio-Half-Mile-To-West-Point.h94370734.Hotel-Information) Highland Falls [](https://www.expedia.ca/Highland-Falls-Hotels-Updated-Home-W-Patio-Half-Mile-To-West-Point.h94370734.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) ![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) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108730000/108722100/108722014/357e067e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly! [](https://www.expedia.ca/New-Canaan-Hotels-Charming-2-BdRm-Cottage-In-Peaceful-New-Canaan.h108722014.Hotel-Information) 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) ![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/d8967df6.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) ![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) ### Lakefront Brewster Vacation Rental w/ Private Dock [](https://www.expedia.ca/Brewster-Hotels-Lakefront-Brewster-Vacation-Rental-W-Private-Dock.h98550476.Hotel-Information) Brewster [](https://www.expedia.ca/Brewster-Hotels-Lakefront-Brewster-Vacation-Rental-W-Private-Dock.h98550476.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/106000000/105550000/105549800/105549790/0b85872b.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) ![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! [](https://www.expedia.ca/Highland-Falls-Hotels-Charming-Highland-Falls-Home-2-Mi-To-West-Point.h105549790.Hotel-Information) 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) 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=2026-01-03&endDate=2026-01-04®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 ![Hampton Inn White Plains/Tarrytown](https://images.trvl-media.com/lodging/1000000/30000/23300/23291/d5b0e16e_y.jpg) ### Hampton Inn White Plains/Tarrytown 10/10 Excellent "Clean room. Cookie time breakfast " [](https://expedia.ca/White-Plains-Hotels-Hampton-Inn-White-Plains.h23291.Hotel-Information) ![EVEN Hotel Norwalk by IHG](https://images.trvl-media.com/lodging/1000000/10000/2600/2584/4cb7d7eb_y.jpg) ### EVEN Hotel Norwalk by IHG 10/10 Excellent "Great hidden gem" [](https://expedia.ca/Stamford-Hotels-EVEN-Hotel-Norwalk.h2584.Hotel-Information) ![Tarrytown House Estate](https://images.trvl-media.com/lodging/1000000/50000/49700/49674/a89a02a1_y.jpg) ### Tarrytown House Estate 10/10 Excellent "Great" [](https://expedia.ca/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information) ![Hotel Nyack, a JdV by Hyatt Hotel](https://images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/a38df02c_y.jpg) ### Hotel Nyack, a JdV by Hyatt Hotel 10/10 Excellent "Accountability is the name of the game here. When I arrived to the hotel, the road was blocked off by firefighters for maybe an hour. I was tired from a long drive, so it was not how I needed to start the check-in process. I ended up parking on the street and walking to the hotel. A small fire in the laundry room was the cause of it all. They had to shut down the elevators, so they were asking everyone to take the stairs. I was tired and had bags, so I decided to go to the bar to wait until the elevators were working again. Accountability is the star here. The manager or someone who may have been a manager walked over to the bar and offered complimentary drinks. The next day I woke up to a notice on the door giving us 50% off the room rate and complimentary breakfast. The hotel is great esthetically, but the customer service takes it over the top. When I got up fornwork the next morning, the restaurant was closed. The person at the fromt desk apologized for that inconvenience and comped 100% of one of my nights there. I didn't fuss or complain about anything. They did all of that on their own and that was very impressive. I will definitely come back to this hotel for future work trips. The rooms look nice. The hotel is clean. No complaints at all. " [](https://expedia.ca/Nyack-Hotels-Hotel-Nyack.h11943081.Hotel-Information) ![The Stamford Hotel](https://images.trvl-media.com/lodging/1000000/50000/42300/42258/d312d428_y.jpg) ### The Stamford Hotel 10/10 Excellent "The room was gear and comfortable " [](https://expedia.ca/Stamford-Hotels-The-Stamford-Hotel.h42258.Hotel-Information) ![Sonesta White Plains Downtown](https://images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg) ### Sonesta White Plains Downtown 10/10 Excellent "Room was spotless. Staff was friendly. A little noisy in the halls at night. " [](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Stamford / New York City](https://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 "Good service " [](https://expedia.ca/Stamford-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Stamford-New-York-City.h24963.Hotel-Information) ![Norwalk Inn & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/15200/15114/13ab5174_y.jpg) ### Norwalk Inn & Conference Center 10/10 Excellent "Amanda has stepped up to took care of my concerns. She did best she could to make me happy. Very professional management " [](https://expedia.ca/Stamford-Hotels-Norwalk-Inn.h15114.Hotel-Information) ![West Gate Inn Nyack](https://images.trvl-media.com/lodging/6000000/5850000/5843400/5843352/393dcf26_y.jpg) ### West Gate Inn Nyack 10/10 Excellent "The profesional and hard working staff. Great location, computer area if you need to and a real buffet breakfast. " [](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 | 295 | | ----------------- | ----------- | | Accommodation | 73 Cottages | | Lowest Price | CA $419 | | Highest Price | CA $1,366 | ## 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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