A clock with 'Winter Park' and 'Central Park' inscribed, surrounded by lush greenery and trees.

Search Chalets in Winter Park

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November 2026

December 2026

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No exact matches found, but these alternatives could be just right

Recommended hotels in Winter Park

A room with a wooden floor, a zebra-patterned rug, wicker furniture, and a view of a balcony with a red table and chairs.

1. Park Plaza Hotel

Park Avenue District

James

AED 777 total

includes taxes & fees

21 Nov - 22 Nov

A hotel with multiple floors, outdoor seating areas, and a well-lit courtyard.

2. The Alfond Inn

Winter Park

Diana

AED 1,262 total

includes taxes & fees

7 Dec - 8 Dec

A Hilton Garden Inn with a classical facade, multiple balconies, and a central entrance with arches.

3. Hilton Garden Inn Winter Park

Winter Park

Crystile

AED 832 total

includes taxes & fees

22 Nov - 23 Nov

A modern hotel entrance with a sign reading "Springhill Suites by Marriott".

4. SpringHill Suites by Marriott Winter Park

Winter Park

WILFREDO

AED 707 total

includes taxes & fees

29 Nov - 30 Nov

A modern building with a glass facade and a central plaza with outdoor seating.

5. Comfy Tiny Home @WP. Large Private Deck+Queen bed

Fairview Shores

AED 676 total

includes taxes & fees

10 Nov - 11 Nov

An outdoor air conditioning unit mounted on a yellow wall, a brick planter with a potted plant, and a white door.

6. 1-bedroom vacation room just 12 minutes from University of Central Florida

Orlando

jamie l.

AED 670 total

includes taxes & fees

16 Nov - 17 Nov

7. Funky Remodeled Otown Bungalow Sleeps 8

Fairview Shores

Julia K.

AED 928 total

includes taxes & fees

7 Dec - 8 Dec

A residential house with a paved driveway, solar panels on the roof, and a well-maintained lawn.

8. Quiet and safe neighborhood come to this great place with lots of room for relax

Orlando

Olubankole S.

AED 1,004 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with white cabinets, a wooden dining table set with white plates and a knife, and a potted plant.

9. Cozy home 5min to Park Ave and Downtown Orlando

Fairview Shores

tyson s.

A wooden exterior with a brown door, a black mat at the entrance, and a small plant to the left.

10. Charming home @wp. Patio +Gazebo. close to highwys

Fairview Shores

Vicki V.

AED 924 total

includes taxes & fees

10 Nov - 11 Nov

A recreational vehicle (RV) parked in a backyard with a patio area, outdoor furniture, and a wooden fence.

11. OASIS UNDER THE OAK TREE.

Goldenrod

"This is a unique and affordable family opportunity in a residential area close to everything. Military friendly host makes you feel like you are safe with family. Plenty of space for spreading out inside the camper that still provides a private closed off space for quiet time. Less than 10 minutes from Full Sail University for visiting students. I enjoyed the quiet neighborhood and the comfortable living in this very cool urban camping setting. Lots of extras available to hang out in the...

Peg W.

AED 488 total

includes taxes & fees

5 Dec - 6 Dec

A red door with a white wall and a black lantern on the left.

12. Mills House @WP. Sleeps 11 Renovated. Queen beds

Fairview Shores

Larry S.

AED 1,133 total

includes taxes & fees

7 Dec - 8 Dec

A single-story house with a front yard, a driveway leading to the entrance, and a small porch area.

13. Spacious 5-bedroom house in gorgeous Winter Park

Winter Park

Hannah F.

AED 1,102 total

includes taxes & fees

8 Nov - 9 Nov

14. Spacious 5-bedroom house in welcoming Winter Park

Winter Park

AED 1,147 total

includes taxes & fees

10 Nov - 11 Nov

A living room with a sofa, coffee table, and decorative wall art.

15. Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence

Goldenrod

Ashley C.

AED 1,614 total

includes taxes & fees

17 Nov - 18 Nov

A modern single-story house with a garage, a covered porch, and a well-maintained lawn.

16. Top 1% Modern Japandi Retreat - Jacuzzi No Fee

Winter Park

Jennifer M.

AED 2,504 total

includes taxes & fees

22 Nov - 23 Nov

A two-story house with a covered patio, a white fence, and a driveway.

17. Luxury Designer Home • Disney, Universal & Downtown

College Park

Christian H.

AED 2,294 total

includes taxes & fees

9 Nov - 10 Nov

18. Cute 5-bedroom house in peaceful Winter Park

Winter Park

Mary Ellen R.

AED 1,106 total

includes taxes & fees

9 Nov - 10 Nov

19. Cute 5-bedroom,6bed house in superb Winter Park.

Winter Park

"We checked in late and were surprised to find half eaten food in the fridge and freezer. Both were very dirty with a noticeable odor. The dishwasher was full of dirty dishes. The oven was full of dirty pans. Most of the dishes in the cupboards had little bits in them as well. There was a fire alarm battery beeping in one of the bedrooms. There was no coffee maker or wine opener or wine glasses or hand soap. There were very few dishes in general, it would have been challenging to cook and serve...

Nyssa S.

AED 1,106 total

includes taxes & fees

30 Nov - 1 Dec

View all properties

Learn more about Winter Park

Stroll through the Morse Museum to see the world's largest collection of Tiffany glass, then boat through the Winter Park Chain of Lakes. Charming Park Avenue offers upscale shopping and outdoor cafés where you can people-watch before catching a sunset concert in Central Park.

See all hotels in Winter Park

Top reviews in Winter Park

The Alfond Inn

Winter Park

10/10 Excellent

Gail

Hilton Garden Inn Winter Park

Winter Park

10/10 Excellent

yvon

SpringHill Suites by Marriott Winter Park

Winter Park

10/10 Excellent

Michelle

Park Plaza Hotel

Park Avenue District

10/10 Excellent

Deborah

A hotel entrance with a covered area, palm trees, and an American flag.

Comfort Suites Downtown

Ivanhoe Village

10/10 Excellent

Glenn

A modern hotel with a glass facade, outdoor seating, and a well-lit entrance.

The Delaney Hotel

South Orange

10/10 Excellent

Chelsea

A multi-story hotel with a prominent red sign, a well-lit entrance, and a landscaped front yard.

Hampton Inn & Suites Orlando Airport @ Gateway Village

Airport North

10/10 Excellent

Christine

A balcony with a table and chairs, overlooking a body of water and buildings.

Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

10/10 Excellent

Amy Dawn

A hotel with a central fountain, palm trees, and a Christmas tree.

Rosen Shingle Creek

Orlando

10/10 Excellent

Narciso

A Holiday Inn Express building with multiple floors, a parking lot with several cars, and a street lamp.

Holiday Inn Express Orlando – South Park by IHG

Orlando

10/10 Excellent

Magdalena

A Holiday Inn Express building with a modern design, featuring a prominent entrance and a covered walkway.

Holiday Inn Express Orlando International Airport by IHG

Orlando

10/10 Excellent

Patricia

A hotel with a central pool surrounded by palm trees and red umbrellas, large buildings with multiple floors, and a clear blue sky.

Universal's Endless Summer Resort - Surfside Inn and Suites

International Drive District

10/10 Excellent

The beginning of a great stay started with Carmen at the front desk. We felt welcomed, informed and appreciated. I read reviews about the hot water, but we had no problem; the shower was great with adequate hot water. The rooms were clean and cleaned daily. The mattresses isn’t plush but I slept well. The shuttle to City Walk and Universal Studios theme parks and early entry into parks was a plus. The restaurant and Starbucks on property were convenient. The property is in a great location and...

Tanya

A modern lounge area with a fireplace, seating, and a bar.

Holiday Inn Orlando - I-Drive North by IHG

International Drive District

10/10 Excellent

Blanca

A modern hotel building with a prominent 'avid' sign, multiple windows, and a covered entrance area.

avid hotel Orlando International Airport by IHG

Orlando

10/10 Excellent

This hotel was just minutes away from the airport and provided a convenient shuttle to and from the terminal. The property was modern, spotless, and offered a great breakfast with plenty of quick options. Alex at the front desk was incredibly kind, helpful, and an absolute pleasure to interact with. Jose, the shuttle driver, went above and beyond by sharing helpful tips about the area and dining options. I would definitely stay here again! Additionally, their sister hotel, located just a few...

Lesen