The Best Winter Park, FL Chalets from $135

A two-story house with a balcony, surrounded by lush greenery and trees.

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Recommended hotels in Winter Park

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

1. Hilton Garden Inn Winter Park

Winter Park

Crystile

$191 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

2. The Alfond Inn

Winter Park

Juan

$331 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

3. SpringHill Suites by Marriott Winter Park

Winter Park

Donna

$201 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

4. Park Plaza Hotel

Park Avenue District

thomas

$196 nightly

Oct 25 - Oct 26

Total with taxes and fees

An aerial view of a residential area with modern buildings, a marina, and a large body of water.

5. Winter Park Spacious Unit - 118

Winter Park

Jorge C.

$286 nightly

Oct 15 - Oct 16

Total with taxes and fees

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

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

Fairview Shores

$185 nightly

Oct 21 - Oct 22

Total with taxes and fees

A two-story residential building with a front entrance, a visible staircase, and a small front yard with plants.

7. Apartment. Downtown Orlando 10 min & Disney 25 min

Fairview Shores

$160 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

8. 1-bedroom vacation room just 12 minutes from University of Central Florida

Orlando

jamie l.

$158 nightly

Nov 2 - Nov 3

Total with taxes and fees

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

9. 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.

$123 nightly

Oct 30 - Oct 31

Total with taxes and fees

10. Funky Remodeled Otown Bungalow Sleeps 8

Fairview Shores

Julia K.

$250 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

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

Fairview Shores

tyson s.

$281 nightly

Oct 15 - Oct 16

Total with taxes and fees

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

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

Orlando

Olubankole S.

$272 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

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

Fairview Shores

Vicki V.

$236 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

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

Fairview Shores

Larry S.

$299 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

15. Spacious 5-bedroom house in gorgeous Winter Park

Winter Park

Hannah F.

$305 nightly

Nov 1 - Nov 2

Total with taxes and fees

16. Cute 5-bedroom house in peaceful Winter Park

Winter Park

Mary Ellen R.

$282 nightly

Oct 19 - Oct 20

Total with taxes and fees

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

17. Luxury Designer Home • Disney, Universal & Downtown

College Park

Cuthbert H.

$556 nightly

Oct 18 - Oct 19

Total with taxes and fees

18. Spacious 5-bedroom house in welcoming Winter Park

Winter Park

$349 nightly

Oct 19 - Oct 20

Total with taxes and fees

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.

$339 nightly

Oct 19 - Oct 20

Total with taxes and fees

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

20. Comfort Suites Downtown

Ivanhoe Village

Marcus

$130 nightly

Oct 18 - Oct 19

Total with taxes and fees

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Top Winter Park Hotel Reviews

Marriott's Grande Vista

10/10 Excellent

"Good place!"

Rosen Inn Lake Buena Vista

8/10 Good

"Falta Mantenimiento en las habitaciones, nos movieron de habitación a las 4 A.M. después de que se activara la alarma de incendio de la habitación más de 3 veces sin motivos, por falta de mantenimiento, no nos resolvieron de inmediato el cambio, sino hasta que pasó varias veces, la nueva habitación tenia tapado el lavamanos."

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent

"This was our first time at Westgate Lakes Resort, and we will definitely come back! We had an amazing and HUGE 2 bedroom unit that overlooked a lake, and it was also very convenient to one of the pools. Also close to the shops, restaurants and main building. We unfortunately had some bad weather and couldn't enjoy the water park, but I went to the fitness center and it was outstanding! All of the staff was helpful, the beds were super comfortable and I even got to enjoy a bubble bath in the huge jacuzzi tub in the master bedroom. There were ample towels, hand towels, toilet paper, paper towels etc. I highly recommend this resort, we were 15 minutes from Universal Theme Parks, as well as only a few minutes from International Drive and other restaurants and the Kia Center. We'll definitely come back, as we visit Orlando often! The only slight negative at all was the check in Friday night was very busy and took a little bit, and also our key stopped working before our check out time but we were able to text the front desk and they set up for us to reactivate our key from the building. Very efficient and nice staff though, Jennica at the front was wonderful and the assistance we got with our bags was so appreciated from the person who also led us to our building. Looking forward to our next trip to hopefully be able to stay at Westgate again!"

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"I absolutely LOVED my stay at Drury. I traveled with my teenager and we stayed for 11 days and could not have been more happier. Manager (AM) at the front desk is nothing short of amazing. The staff and shuttle drivers are absolutely incredible and definitely go above and beyond. The breakfast was delicious and had many options, from cereal, to eggs, potatoes, Mickey waffles, fruit, biscuits, and gravy and so much more. They’re 530. Dinner was absolutely delicious as well and adults. Get free drinks during this time. Our room had a balcony overlooking the pool and was able to see the fireworks every night. Our stay was nothing short of magical."

Find out more about Winter Park

Winter Park Chalets information

Number of reviews	2,184
Accommodation	11 Chalets
Lowest Price	$135
Highest Price	$621

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Recommended hotels in Winter Park

1. Hilton Garden Inn Winter Park

2. The Alfond Inn

3. SpringHill Suites by Marriott Winter Park

4. Park Plaza Hotel

5. Winter Park Spacious Unit - 118

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

7. Apartment. Downtown Orlando 10 min & Disney 25 min

8. 1-bedroom vacation room just 12 minutes from University of Central Florida

9. OASIS UNDER THE OAK TREE.

10. Funky Remodeled Otown Bungalow Sleeps 8

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

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

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

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

15. Spacious 5-bedroom house in gorgeous Winter Park

16. Cute 5-bedroom house in peaceful Winter Park

17. Luxury Designer Home • Disney, Universal & Downtown

18. Spacious 5-bedroom house in welcoming Winter Park

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

20. Comfort Suites Downtown

Find vacation rentals that suit your style

Top Winter Park Hotel Reviews

Marriott's Grande Vista

Evermore Orlando Resort

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Hyatt Regency Orlando International Airport

Rosen Inn Lake Buena Vista

Universal's Endless Summer Resort - Dockside Inn and Suites

Westgate Lakes Resort & Spa Universal Studios Area

Drury Plaza Hotel Orlando - Disney Springs Area

Find out more about Winter Park

Winter Park Chalets information

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