Hotels in Downtown, Winter Park

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Booking Insights
Recommended by KAYAK

Best hotels in Downtown (Winter Park)

The Alfond Inn - Winter Park - Building
The Alfond Inn
0.2 mi from Downtown, Winter Park, United States
9.2Wonderful(381)
Free Wi-Fi
Pool
Pet friendly
Spa
$451+
Check availability
Park Plaza Hotel - Winter Park - Lobby
Park Plaza Hotel
0.2 mi from Downtown, Winter Park, United States
7.8Good(600)
Free Wi-Fi
Pet friendly
$211+
Check availability
Ada Compliant Room - Contemporary Furnishings - Rooftop Pool - Close To Parks - Winter Park - Lobby
Ada Compliant Room - Contemporary Furnishings - Rooftop Pool - Close To Parks
0.2 mi from Downtown, Winter Park, United States
$488+
Check availability
Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations - Winter Park - Lobby
Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations
0.2 mi from Downtown, Winter Park, United States
$617+
Check availability
Booking Insights

KAYAK’s insights for hotels in Downtown

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Downtown with confidence.

Which month has the cheapest hotel rates in Downtown?

Hotels are cheapest in Downtown in September, with average rates of $200. In comparison, March is the most expensive month, with prices at $635.

What is the cheapest day of the week to book a hotel in Downtown?

Saturday offers the lowest rates in Downtown, with an average nightly price of $315. The highest prices are found on Wednesday, with average rates at $535.

How much is a hotel in Downtown for tonight?

The best deal for a 3-star hotel room in Downtown found by KAYAK users in the last 3 days was $220, while a 4-star hotel the lowest price was $368. The cheapest room found overall was for $220.

How much is a hotel in Downtown for this weekend?

The cheapest hotel room in Downtown for the upcoming weekend found on KAYAK in the last 3 days was for $225 per night. For the same dates, 3-star hotel rooms have been found for as low as $225 per night and 4-star hotel rooms from $352 per night.

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How much is a Downtown hotel?

Here are our most popular & best value hotels

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

September
March
$440
$369
Cheapest month to stay with an average 44% drop in price.
Most expensive month to stay with an average 79% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding a hotel deal in Downtown

  • If you’re looking for a cheap hotel in Downtown, you should consider going during the low season. You’ll generally find lower-priced hotels in Downtown in September and May.
  • If you’re looking for a bargain then KAYAK data shows that you’ll find the best hotel deals in Downtown (Winter Park) if you stay on a Saturday. On the other hand, the most expensive day for hotel bookings is Wednesday.
  • If you’re looking for a last minute bargain, the cheapest 3-star hotel in Downtown (Winter Park) found on KAYAK in the last 2 weeks was $204, while the most expensive was $249.
  • Not sure just how much there is to see and do in Downtown? KAYAK users usually book their hotel here for 3 days.

FAQs when booking a hotel in Downtown

  • What are the best hotels in Downtown?

    Downtown is a great part of Winter Park to make your base. If you’re staying in Downtown area then Park Plaza Hotel, The Alfond Inn, and Ada Compliant Room - Contemporary Furnishings - Rooftop Pool - Close To Parks are all recommended on KAYAK.

  • Which hotels in Downtown are romantic?

    If you’re looking for a romantic break with your partner in Downtown, then why not stay at Park Plaza Hotel, which have been recommended by KAYAK users as great for couples.

Where to stay in Downtown?

Our map will help you find the perfect hotel in Downtown, Winter Park by showing you the exact location of each hotel.

Everything you need to know for your stay in Winter Park