Title: Florida Vacation Home Rentals from CA $277: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Florida](https://expedia.ca/Florida-Hotels.d553248634999031091.Travel-Guide-Hotels)[Vacation Rentals in Florida](https://expedia.ca/Florida-Vacation-Rentals.d553248634999031091.Travel-Guide-VacationRentals)[Florida Car Rentals](https://expedia.ca/Car-Rentals-In-Florida.d553248634999031091.Car-Rental-Guide)[Florida Vacation Packages](https://expedia.ca/Florida.d553248634999031091.Destination-Travel-Guides) ![Two beautiful cascades that combine and form several crystal clear pools along the stream. ](https://images.trvl-media.com/place/553248634999031091/a1407374-cf5a-4fd5-91c7-15f31fa15fae.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Chris Addams # Florida Vacation Rentals - ![](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 [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&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) In one month [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Florida vacation homes ![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/6c6cf45f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/972c3b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/5dc2bebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90260000/90251100/90251080/12b81391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Florida Mountain Log Cabin [](https://www.expedia.ca/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.Hotel-Information) Florida 10/10 Exceptional (4) "Place was super clean. Beds were comfortable. Location was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tristan e. CA $253 CA $467 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/North-Adams-Hotels-Florida-Mountain-Log-Cabin.h90251080.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/f2b309c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/c910a979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/7b0a2e19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119140000/119137900/119137863/c5e9caf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Greylock Cabin [](https://www.expedia.ca/North-Adams-Hotels-True-Cabin-In-The-Woods-New-Log-Cabin-With-View-Of-Mt-Greylock.h119137863.Hotel-Information) Florida 10/10 Exceptional (4) "Wonderful view, peaceful quiet area, cosy cabin." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $289 CA $510 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/North-Adams-Hotels-True-Cabin-In-The-Woods-New-Log-Cabin-With-View-Of-Mt-Greylock.h119137863.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/01ff54d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/7e27ff2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, offices](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/512b2604.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/d695e72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovely 2nd Floor Apartment [](https://www.expedia.ca/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information) Greenfield 10/10 Exceptional (46) "Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy M. CA $160 CA $277 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/493cc38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/e8d7246a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/010523ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61480000/61478200/61478133/aac07fd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat [](https://www.expedia.ca/Bennington-Hotels-Two-Brooks-Lodge.h61478133.Hotel-Information) Bennington 8.6/10 Excellent (34) "The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Malika R. CA $138 CA $374 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Bennington-Hotels-Two-Brooks-Lodge.h61478133.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/c4a5d927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/ba382757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/929abf3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/41000000/40230000/40226600/40226569/fc1c3458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas! [](https://www.expedia.ca/Hoosick-Falls-Hotels-Cozy-Ski-Retreat-With-New-Pet-Yard-And-Many-Upgrades-Close-To-3-Ski-Areas.h40226569.Hotel-Information) Hoosick Falls 9.8/10 Exceptional (99) "Quiet and relaxing property " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle S. CA $160 CA $428 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Hoosick-Falls-Hotels-Cozy-Ski-Retreat-With-New-Pet-Yard-And-Many-Upgrades-Close-To-3-Ski-Areas.h40226569.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/9530dfe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/c459a4e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/962a1a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/17e097bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Glass House nestled in the Vermont wilderness! [](https://www.expedia.ca/Brattleboro-Hotels-Stunning-Glass-House-Nestled-In-The-Vermont-Wilderness.h111133438.Hotel-Information) Guilford 10/10 Exceptional (1) "The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Grant D. CA $198 CA $569 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Brattleboro-Hotels-Stunning-Glass-House-Nestled-In-The-Vermont-Wilderness.h111133438.Hotel-Information) ![Game room](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/f112c530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/78692cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/3d011b8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/4702110d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Couples 2 Bedroom Retreat-Close to Shelburne Falls [](https://www.expedia.ca/Colrain-Hotels-Couples-2-Bedroom-Retreat-Hot-Tub-Air-Hockey-Close-To-ShelburneFalls.h113519074.Hotel-Information) Colrain 10/10 Exceptional (4) "This place was great! Even though it was raining we enjoyed the hot tub! It was super clean and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) KayKay S. CA $213 CA $485 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Colrain-Hotels-Couples-2-Bedroom-Retreat-Hot-Tub-Air-Hockey-Close-To-ShelburneFalls.h113519074.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/eab00089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/3d81b129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/296ae5ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/6cb471c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed [](https://www.expedia.ca/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information) Whitingham 10/10 Exceptional (14) "Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacklyn D. CA $365 CA $813 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/bdc7550f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/a38bbe4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/811d3663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions! [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) Pittsfield 7.8/10 Good (6) "Very clean and spacious! We enjoyed our stay with our small pup!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann C. CA $371 CA $666 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w907h683x58y0-59aad182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w510h683x258y0-04b5e846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, printers](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w919h683x60y0-f3238385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/61000000/60770000/60763800/60763766/w524h683x260y0-f1656d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Getaway Cottage [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Getaway-Or-Remote-Workschool-Location.h60763766.Hotel-Information) Williamstown 9.2/10 Wonderful (24) "The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Alice H. CA $322 CA $657 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Getaway-Or-Remote-Workschool-Location.h60763766.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/c077bee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/b4b598c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/1ae2e1b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/eb8c4f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FaLL Western Mass Getaway-Airhockey-Firepit [](https://www.expedia.ca/Colrain-Hotels-10-Guests-5-BR.h37817199.Hotel-Information) Colrain 9.8/10 Exceptional (38) "Great house for family gatherings " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) John Paul B. CA $552 CA $1,086 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Colrain-Hotels-10-Guests-5-BR.h37817199.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/4501ee4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/bdac3cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/w1170h1596x0y468-0a8fb230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/3902b9c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table. [](https://www.expedia.ca/West-Dover-Hotels-Fantastic-Location-Mt-Snow-Ski-Off.h101085488.Hotel-Information) Dover 10/10 Exceptional (5) "We enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $371 CA $867 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/West-Dover-Hotels-Fantastic-Location-Mt-Snow-Ski-Off.h101085488.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/103000000/102820000/102812000/102811958/847f54ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, offices](https://images.trvl-media.com/lodging/103000000/102820000/102812000/102811958/047fb1c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102820000/102812000/102811958/16a332d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102820000/102812000/102811958/a7801845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access! [](https://www.expedia.ca/Wilmington-Hotels-Newly-Updated-Vermont-Getaway-For-All-Occasions.h102811958.Hotel-Information) Wilmington 10/10 Exceptional (17) "Great place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jack & Heather G. CA $329 CA $858 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Wilmington-Hotels-Newly-Updated-Vermont-Getaway-For-All-Occasions.h102811958.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/f305b62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/037efde9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/38972098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/d80b29aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverbend Berkshire East Basecamp - 3 bedrooms available [](https://www.expedia.ca/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.Hotel-Information) Charlemont CA $220 CA $566 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/0c3d5316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/dd79e367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video games, table tennis](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/bf925c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/1e5be588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MtSnow\* HotTub\* Pool \* AirHockey\*PingPong \* Darts [](https://www.expedia.ca/Wilmington-Hotels-MtSnow-HotTub-Pool-AirHockeyPingPong-Darts.h119097866.Hotel-Information) Wilmington CA $342 CA $943 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Wilmington-Hotels-MtSnow-HotTub-Pool-AirHockeyPingPong-Darts.h119097866.Hotel-Information) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/63000000/62990000/62985400/62985395/ea01aa18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/63000000/62990000/62985400/62985395/540ed4c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/63000000/62990000/62985400/62985395/95b48de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/63000000/62990000/62985400/62985395/aa5180d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun [](https://www.expedia.ca/Wilmington-Hotels-Vermont-Family-Winter-Oasis.h62985395.Hotel-Information) Wilmington 10/10 Exceptional (52) "We were a group of 11 and we had a great weekend. Comfortable to stay and plenty to do!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olivia R. CA $411 CA $1,033 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Wilmington-Hotels-Vermont-Family-Winter-Oasis.h62985395.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/cb4793bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/w1008h683x16y0-213f51bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/11a36f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/68000000/67640000/67635500/67635438/d4f0c0c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con [](https://www.expedia.ca/Hancock-Hotels-Spacious-3BR-3BA-Ski-OnOff-Jiminy-Mountain-Resort.h67635438.Hotel-Information) Hancock 9.8/10 Exceptional (72) "We had a wonderful stay, thank you! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary L. CA $364 CA $757 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Hancock-Hotels-Spacious-3BR-3BA-Ski-OnOff-Jiminy-Mountain-Resort.h67635438.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/c7eb5681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic House | Private kitchen](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/f721b80c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic House | Water view](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/7c1d02ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic House | Private kitchen](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/6511d75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Brooks Lodge [](https://www.expedia.ca/Bennington-Hotels-Two-Brooks-Lodge.h83780792.Hotel-Information) Bennington 4.8/10 (3) "Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hunter [](https://www.expedia.ca/Bennington-Hotels-Two-Brooks-Lodge.h83780792.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/110000000/109390000/109380700/109380657/f920340a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/110000000/109390000/109380700/109380657/w2590h2130x250y0-6ccd0240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109390000/109380700/109380657/e3130fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109390000/109380700/109380657/10545ad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow [](https://www.expedia.ca/West-Dover-Hotels-Game-Rm.h109380657.Hotel-Information) Dover 9.0/10 Wonderful (2) "Weekend stay.Clean, comfortable, well equipped. Was as advertised.I would stay there again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noah K. CA $438 CA $974 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/West-Dover-Hotels-Game-Rm.h109380657.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c8837e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/w1440h1084x0y1-9f76bc91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/5d0aa061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/34fa691f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hancock Village Inn Near Jiminy Peak [](https://www.expedia.ca/Pittsfield-Hotels-Hancock-Village-Inn-At-Jiminy-Peak.h89806253.Hotel-Information) Hancock 10/10 Exceptional (16) "Amazing Inn. Cozy and everything we needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Price F. CA $811 CA $1,514 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Pittsfield-Hotels-Hancock-Village-Inn-At-Jiminy-Peak.h89806253.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=2025-12-27&endDate=2025-12-28®ionId=553248634999031091&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Florida%2C+Massachusetts%2C+United+States+of+America®ionId=553248634999031091&latLong=42.666752%2C-73.011215&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=CABIN) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Florida%2C+Massachusetts%2C+United+States+of+America®ionId=553248634999031091&latLong=42.666752%2C-73.011215&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=CHALET) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Florida%2C+Massachusetts%2C+United+States+of+America®ionId=553248634999031091&latLong=42.666752%2C-73.011215&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Florida%2C+Massachusetts%2C+United+States+of+America®ionId=553248634999031091&latLong=42.666752%2C-73.011215&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=VACATION_HOME) Condos [](https://www.expedia.ca/Hotel-Search?destination=Florida%2C+Massachusetts%2C+United+States+of+America®ionId=553248634999031091&latLong=42.666752%2C-73.011215&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=CONDO) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Florida%2C+Massachusetts%2C+United+States+of+America®ionId=553248634999031091&latLong=42.666752%2C-73.011215&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Florida%2C+Massachusetts%2C+United+States+of+America®ionId=553248634999031091&latLong=42.666752%2C-73.011215&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=APARTMENT) Villas [](https://www.expedia.ca/Hotel-Search?destination=Florida%2C+Massachusetts%2C+United+States+of+America®ionId=553248634999031091&latLong=42.666752%2C-73.011215&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=VILLA) ![](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%2FFlorida-Private-Vacation-Homes.d553248634999031091-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FFlorida-Private-Vacation-Homes.d553248634999031091-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Florida Hotel Reviews ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Hot tub was relaxing. Parking was easy. Restaurant within walking distance. If you forget anything dollar general close." [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Knotty Pine](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/439bea3f_y.jpg) ### Knotty Pine 10/10 Excellent "Yes" [](https://expedia.ca/Bennington-Hotels-Knotty-Pine.h119106200.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick. " [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Clean spacious toom" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Great staff especially Katherine " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Hampton Inn Bennington](https://images.trvl-media.com/lodging/2000000/1200000/1192000/1191981/aadd5504_y.jpg) ### Hampton Inn Bennington 10/10 Excellent "Yes" [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-Bennington.h1191981.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Spacious rooms. Attentive staff. Free parking behind the hotel." [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Best Western Bennington](https://images.trvl-media.com/lodging/1000000/20000/16400/16323/5ad1b90e_y.jpg) ### Best Western Bennington 10/10 Excellent "Yes" [](https://expedia.ca/Bennington-Hotels-Best-Western-Bennington.h16323.Hotel-Information) ![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "My room was so big! Very clean, huge bathroom, claw foot tub. Highly recommend this place. It had a great vibe. Was not industrial like a hotel, had a very clean and comforting feeling, like you were visiting a relative. I stayed here for my brother’s wedding at MoCA. Great experience all around. Definitely will be back. " [](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ## Find out more about Florida ## Florida Vacation Homes information | Number of reviews | 434 | | ----------------- | ------------------ | | Accommodation | 418 Vacation Homes | | Lowest Price | CA $277 | | Highest Price | CA $1,514 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in North Adams ](https://www.expedia.ca/4Star-North-Adams-Hotels.s40-0-d9137.Travel-Guide-Filter-Hotels) - [Farmstay in Adams ](https://www.expedia.ca/Adams-Agritourism.d6005393-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Adams ](https://www.expedia.ca/Adams-Apart-Hotels.d6005393-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Adams ](https://www.expedia.ca/Adams-Bed-And-Breakfast.d6005393-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Adams ](https://www.expedia.ca/Adams-Chalets.d6005393-aaChalets.Travel-Guide-Accommodation) - 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