Title: Highland City Cottages from CA $118 | Expedia.ca [Highland City Travel Guide](https://expedia.ca/Highland-City.dx553248635975864405)[Hotels in Highland City](https://expedia.ca/Highland-City-Hotels.d553248635975864405.Travel-Guide-Hotels)[Vacation Rentals in Highland City](https://expedia.ca/Highland-City-Vacation-Rentals.d553248635975864405.Travel-Guide-VacationRentals)[Highland City Car Rentals](https://expedia.ca/Car-Rentals-In-Highland-City.d553248635975864405.Car-Rental-Guide)[Highland City Vacation Packages](https://expedia.ca/Highland-City.d553248635975864405.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Highland City Cottage Rentals from CA $118 ![](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 [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975864405&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975864405&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635975864405&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635975864405&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) ## Browse Select Highland City Cottages ![Exterior](https://images.trvl-media.com/lodging/90000000/89640000/89635100/89635062/d94a6bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/90000000/89640000/89635100/89635062/5bc04f02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89640000/89635100/89635062/3f617b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/90000000/89640000/89635100/89635062/84a3bb73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Cottage Near Legoland & Chain of Lakes Lake Hamilton 10/10 Exceptional (6) "This place is tiny but everything you need for a comfortable stay! Would definitely stay here again." CA $140 CA $290 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Lake-Hamilton-Hotels-Luxury-Cottage-Near-Legoland-Chain-Of-Lakes.h89635062.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/ad468c68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/a7d343f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/1d7e29a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/110000000/109310000/109302000/109301943/6887a27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn Winter Haven 10/10 Exceptional (2) "Just what we needed for a weekend trip with our grandsons for the weekend " CA $160 CA $389 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Winter-Haven-Hotels-Sweet-Cottage-5-Mi-To-Legoland-05-Mi-To-Dwntwn.h109301943.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/50a06dbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed, Non Smoking | Living area](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/9828479e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/a66b5fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed, Non Smoking | Private kitchenette](https://images.trvl-media.com/lodging/33000000/32740000/32732600/32732561/4549c4d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Ida Beach Resort Winter Haven 7.4/10 Good (179) "This room served my needs well. I enjoyed the full kitchen and bathtub." CA $105 CA $118 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Winter-Haven-Hotels-Lake-Ida-Beach-Resort.h32732561.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/3e94c18f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/417eb849.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/961c6be6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93532600/93532553/56573fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn Winter Haven 10/10 Exceptional (3) "We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again." CA $217 CA $526 total includes taxes & fees Oct 11 - Oct 12 [](https://www.expedia.ca/Winter-Haven-Hotels-Lovely-Lakefront-Home-W-Grill-7-Mi-To-Legoland.h93532553.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/117000000/116840000/116838100/116838053/98f7a925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/117000000/116840000/116838100/116838053/a40dabb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/117000000/116840000/116838100/116838053/b697b6eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/117000000/116840000/116838100/116838053/97b23f55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southern Dunes Family Retreat: Hot Tub & Game Room Haines City CA $161 CA $510 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Haines-City-Hotels-Southern-Dunes-Family-Retreat-Hot-Tub-Game-Room.h116838053.Hotel-Information) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/6919bd78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/4b563550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/034df557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117620000/117619900/117619898/70c3f621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Historic Cottage with Cozy Porch and Garden Retreat Polk City CA $176 CA $374 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Polk-City-Hotels-Charming-Historic-Cottage-With-Cozy-Porch-And-Garden-Retreat.h117619898.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=2025-10-24&endDate=2025-10-25®ionId=553248635975864405&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%2FHighland-City-Cottages.d553248635975864405-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHighland-City-Cottages.d553248635975864405-aaCottages.Travel-Guide-Accommodation) ## Top Highland City Hotel Reviews ![La Quinta Inn & Suites by Wyndham Lakeland West](//images.trvl-media.com/lodging/1000000/90000/84700/84646/58543b1b_y.jpg) ### La Quinta Inn & Suites by Wyndham Lakeland West 10/10 Excellent "Restaurants in walking distance. Nice weather. Got to enjoy the pool. " [](https://expedia.ca/Lakeland-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lakeland-West.h84646.Hotel-Information) ![Staybridge Suites Winter Haven Auburndale by IHG](//images.trvl-media.com/lodging/95000000/94680000/94674300/94674232/0585f081_y.jpg) ### Staybridge Suites Winter Haven Auburndale by IHG 10/10 Excellent "The room was very spacious and clean " [](https://expedia.ca/Winter-Haven-Hotels-Staybridge-Suites-Winter-Haven-Auburndale.h94674232.Hotel-Information) ![Howard Johnson by Wyndham Lakeland](//images.trvl-media.com/lodging/1000000/10000/9600/9597/6ad2183e_y.jpg) ### Howard Johnson by Wyndham Lakeland 10/10 Excellent "Staff was incredibly friendly and accommodating. " [](https://expedia.ca/Lakeland-Hotels-Howard-Johnson-By-Wyndham-Lakeland.h9597.Hotel-Information) ![Holiday Inn Winter Haven by IHG](//images.trvl-media.com/lodging/1000000/10000/7900/7835/1b5518c0_y.jpg) ### Holiday Inn Winter Haven by IHG 10/10 Excellent "Clean!!!" [](https://expedia.ca/Winter-Haven-Hotels-Holiday-Inn-Winter-Haven.h7835.Hotel-Information) ![Motel 6 Lakeland, FL](//images.trvl-media.com/lodging/1000000/990000/988800/988786/361b1343_y.jpg) ### Motel 6 Lakeland, FL 10/10 Excellent "Loved it" [](https://expedia.ca/Lakeland-Hotels-Motel-6-Lakeland.h988786.Hotel-Information) ![Travelodge by Wyndham Lakeland](//images.trvl-media.com/lodging/4000000/3570000/3566100/3566069/b74ce246_y.jpg) ### Travelodge by Wyndham Lakeland 10/10 Excellent "Clean room and kind staff" [](https://expedia.ca/Lakeland-Hotels-Travelodge-By-Wyndham-Lakeland.h3566069.Hotel-Information) ![Best Western Plus Winter Haven Inn & Suites ](//images.trvl-media.com/lodging/92000000/91030000/91030000/91029909/b48185c3_y.jpg) ### Best Western Plus Winter Haven Inn & Suites  10/10 Excellent "Friendly staff comfortable and well designed rooms " [](https://expedia.ca/Winter-Haven-Hotels-Best-Western-Plus-Winter-Haven-Inn-Suites.h91029909.Hotel-Information)  ![Days Inn & Suites by Wyndham Lakeland](//images.trvl-media.com/lodging/2000000/1640000/1635700/1635682/9412c3cb_y.jpg) ### Days Inn & Suites by Wyndham Lakeland 10/10 Excellent "We have stayed here before and will choose this place again." [](https://expedia.ca/Lakeland-Hotels-Days-Inn-Suites-By-Wyndham-Lakeland.h1635682.Hotel-Information) ![Home2 Suites By Hilton Winter Haven](//images.trvl-media.com/lodging/107000000/106210000/106204500/106204409/533a79f7_y.jpg) ### Home2 Suites By Hilton Winter Haven 10/10 Excellent "Excellent " [](https://expedia.ca/Winter-Haven-Hotels-Home2-Suites-By-Hilton-Winter-Haven.h106204409.Hotel-Information) ## Find out more about Highland City ## Highland City Cottages information | Number of reviews | 182 | | --- | --- | | Accommodation | 125 Cottages | | Lowest Price | CA $118 | | Highest Price | CA $526 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - More ways to book - [Aparthotels in Bartow](https://www.expedia.ca/Bartow-Apart-Hotels.d6397-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Bartow](https://www.expedia.ca/Bartow-Bed-And-Breakfast.d6397-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Holiday Park Resorts in Bartow](https://www.expedia.ca/Bartow-Holiday-Parks.d6397-aaHolidayParks.Travel-Guide-Accommodation) - 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[Resorts in Longboat Key](https://www.expedia.ca/Longboat-Key-Resort-Hotels.d8409-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Longboat Key](https://www.expedia.ca/Longboat-Key-Townhomes.d8409-aaTownhomes.Travel-Guide-Accommodation) - [Treehouses in Longboat Key](https://www.expedia.ca/Longboat-Key-Treehouses.d8409-aaTreehouses.Travel-Guide-Accommodation) - [Villas in Longboat Key](https://www.expedia.ca/Longboat-Key-Villas.d8409-aaVillas.Travel-Guide-Accommodation) - [Aparthotels in Pinellas Park](https://www.expedia.ca/Pinellas-Park-Apart-Hotels.d9113-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Pinellas Park](https://www.expedia.ca/Pinellas-Park-Bed-And-Breakfast.d9113-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Pinellas Park](https://www.expedia.ca/Pinellas-Park-Guest-Houses.d9113-aaGuestHouses.Travel-Guide-Accommodation) - [Holiday Park Resorts in Pinellas Park](https://www.expedia.ca/Pinellas-Park-Holiday-Parks.d9113-aaHolidayParks.Travel-Guide-Accommodation) - 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[Lodges in Polk County](https://www.expedia.ca/Polk-County-Lodges.d553248635083907427-aaLodges.Travel-Guide-Accommodation) - [Resorts in Polk County](https://www.expedia.ca/Polk-County-Resort-Hotels.d553248635083907427-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near The Circle B Bar Reserve](https://www.expedia.ca/The-Circle-B-Bar-Reserve-Hotels.0-l553248633992476653-0.Travel-Guide-Filter-Hotels) - [Hotels near The Club at Eaglebrooke](https://www.expedia.ca/The-Club-At-Eaglebrooke-Hotels.0-l553248621532652781-0.Travel-Guide-Filter-Hotels) - [Hotels near Walt Disney World® Resort](https://www.expedia.ca/Walt-Disney-World-Resort-Hotels.0-l6034120-0.Travel-Guide-Filter-Hotels) - [Flights to Florida](https://www.expedia.ca/Destinations-In-Florida.d211.Flight-Destinations) - [Flights from Toronto (YYZ) to Orlando (MCO)](https://www.expedia.ca/lp/flights/yyz/mco/toronto-to-orlando) - [Bramble Ridge Golf Course](https://www.expedia.ca/Bramble-Ridge-Golf-Course-Lakeland.d6182473.Vacation-Attraction) - [Visit Eaton Park](https://www.expedia.ca/Eaton-Park.dx3000431012) - [Sanlan Bird and Wildlife Sanctuary](https://www.expedia.ca/Sanlan-Bird-And-Wildlife-Sanctuary-Lakeland.d6182481.Vacation-Attraction) - [Book Cottages in Highland City on Expedia.com](https://www.expedia.com/Highland-City-Cottages.d553248635975864405-aaCottages.Travel-Guide-Accommodation)