Title: Book the Best Florida LUXURY Hotels - Upscale Hotels in Florida, MA | 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) ![](https://mediaim.expedia.com/destination/2/24e6a66c6164d8030df4681f43cd39e6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Chris Addams # Find luxury hotels in Florida, MA - ![](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 availability on Florida Luxury Hotels Tonight [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-11-05&endDate=2025-11-06&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Nov 6 - Nov 7](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-11-06&endDate=2025-11-07&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-11-14&endDate=2025-11-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Florida Luxury Hotels ## Top Florida Hotel Reviews ![Vacation Village in the Berkshires](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "The amenities are great. The pool and hot tub are very comfortable temperatures, pool tables, ping pong, foosball, arcade games, movie theater, and more." [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Lovely hotel in the middle of a non very busy town. " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Hotel Vervana, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/b33626c2_y.jpg) ### Hotel Vervana, Trademark Collection by Wyndham 10/10 Excellent "Everything was beautiful. Room was clean. Very spacious. Comfortable. Staff was kind. Location. Location. Location. Will recommend. And be back again. Thank you." [](https://expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "The restaurant was so delicious …the fries were the best fries I have ever had …will never forget how tasty they were !!!" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Hampton Inn Bennington](//images.trvl-media.com/lodging/2000000/1200000/1192000/1191981/aadd5504_y.jpg) ### Hampton Inn Bennington 10/10 Excellent "The breakfast was exceptional there was a lot of options to choose from the rooms are very clean we enjoyed our stay" [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-Bennington.h1191981.Hotel-Information) ![The Porches Inn at Mass MoCA](//images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "peaceful" [](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Good value. A good place." [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![FairBridge Inn Express](//images.trvl-media.com/lodging/1000000/10000/1600/1543/abb5a87f_y.jpg) ### FairBridge Inn Express 10/10 Excellent "Heating fine. Room warm" [](https://expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.Hotel-Information) ![Jiminy Peak Mountain Resort](//images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830_y.jpg) ### Jiminy Peak Mountain Resort 10/10 Excellent "This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay." [](https://expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ## Frequently asked questions ### Are you looking for a luxury hotel for your Florida vacation? > Use Expedia and let us help you arrange a flight to Pittsfield, MA (PSF-Pittsfield Municipal) airport or Albany Intl. Airport (ALB) airport, and then select from different places to stay that will deliver the luxury you want. Amenities are an important consideration when you plan a vacation, so we make it easy to find what you want to make your stay relaxing and comfortable. If you want a posh hotel that has a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Florida has to offer. Florida has some interesting things to see and do including Deerfield River and Green Mountain National Forest, so you might want to take in the local sights during your visit. ### When can I expect good weather in Florida? > Planning for the weather is a good way to make your trip to Florida relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Florida are January, March, February, and November, with each month seeing an average of 7 inches of snowfall. ### What's there to see and do in Florida? > Experience Florida with a stop at Deerfield River, Green Mountain National Forest, and Florida Town Hall. 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