Title: Book the Best ROMANTIC Hotels in Florida, MA from CA $160 - Florida Romantic Getaways | 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 Romantic Hotels in Florida, MA from CA $160 ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Check availability on Florida Romantic Hotels Tonight [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-10-06&endDate=2025-10-07&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-10-07&endDate=2025-10-08&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-10-10&endDate=2025-10-12&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248634999031091&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Florida Romantic Hotels ![Front of property](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/0d3a6bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/81dd974d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/7fbb1dec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Carriage House C](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/8a063a5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Colonel Williams Inn Brattleboro 9.8/10 Exceptional (329) "Very nice historic inn. We enjoyed our stay. Breakfast was exceptional." CA $202 CA $223 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/7b825179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/542dbb84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/38e7a71c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/3033684f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### UU Rowe Camp and Conference Center Rowe CA $203 CA $215 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Rowe-Hotels-UU-Rowe-Camp-And-Conference-Center.h110897047.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a25612d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (893) "Excellent customer service and great rooms" CA $144 CA $160 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/d48c4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/1ea731f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/f3e43c7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Williams Inn Williamstown 9.6/10 Exceptional (515) "Nice place to stay for a wedding " CA $277 CA $310 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/ed219351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/04000126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/a8d66378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/5200a28c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den Dover 9.4/10 Exceptional (16) "So cute and in such a great area! It was a perfect stay" CA $60 CA $363 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-Den.h36778065.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/dfd331b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/ec7f96e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/11b23fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/4aef8677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wilmington Inn Wilmington 10/10 Exceptional (185) "Breakfast great, staff accommodating, Charlie and crew, made you feel like going to grandmas!" CA $287 CA $326 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Wilmington-Hotels-The-Wilmington-Inn.h3532068.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/afbb4318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/9becd207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/4e933c7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/8c4366ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Village Carriage House - Super Private!! Lanesborough 9.8/10 Exceptional (259) "We enjoyed our stay. Excellent location to explore Western Mass!" CA $209 CA $319 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/6f32fa47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/b3ee4f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/ffb7a388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/8a6408f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbour House Inn Cheshire 9.4/10 Exceptional (52) "We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! " CA $344 CA $364 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/0f420ffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/a0178b1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/a975c57b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/7ac1beb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### South Shire Bennington 9.2/10 Wonderful (110) "Beautiful place to stay " CA $219 CA $248 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Bennington-Hotels-South-Shire.h76163190.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/89000000/88740000/88730700/88730696/4a7d2d8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/89000000/88740000/88730700/88730696/ef464910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/89000000/88740000/88730700/88730696/dd84fb54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Farmhouse 3, Signature Room, 1 King Bed and 1 Twin Sofa Bed, Non Smoking](https://images.trvl-media.com/lodging/89000000/88740000/88730700/88730696/df1eb844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Farm Road Estate West Dover 10/10 Exceptional (71) "very helpful and friendly staff - they goes above and beyond. the room/bed everything is so comfortable and the place is beautiful." CA $206 CA $303 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/West-Dover-Hotels-Farm-Road-Estate.h88730696.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=2025-10-21&endDate=2025-10-22®ionId=553248634999031091&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## 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 "Great!" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 "Great place to spend an autumn night." [](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.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 "Friendly staff easy check in accessible to different places" [](https://expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.Hotel-Information) ![Best Western Bennington](//images.trvl-media.com/lodging/1000000/20000/16400/16323/5ad1b90e_y.jpg) ### Best Western Bennington 10/10 Excellent "Great stay" [](https://expedia.ca/Bennington-Hotels-Best-Western-Bennington.h16323.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 "Cool" [](https://expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.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 "Valerie at the front desk and who checked me in was above and beyond in customer service. She checked to see if I had a IGH account—which I did but had forgotten, and reminded me about the points and promotions. This Holiday Inn is a well managed property. Thank you" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Florida? > If you and your partner need some romantic time away, we'd like to help you plan for it. If you'd like to explore some of the area's notable sights, you might make a stop by Deerfield River, Green Mountain National Forest, or Reed Brook Preserve. If you're interested in staying near a certain attraction, you can sort by neighborhood or distance to top sights, so you'll be able to see everything on your list. ### When is the best time of year for a romantic getaway to Florida? > If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Florida: 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 is there to do in Florida? > There's nothing better than wandering around a new place with your sweetheart, so consider checking out all there is to see and do in Florida. You might think about visiting Deerfield River, Green Mountain National Forest, or Reed Brook Preserve. ### What's the best way to get to Florida and around town during my romantic getaway? > This information about transportation options in Florida might help your romantic trip go off without a hitch: Make your way to Florida with a flight to Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest major airport located 22 mi (35.3 km) from the city center. 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