Photo by Kayla Templin

Find hotels with pools in Old Town Winter Park, Winter Park from $99

Start date: Check-in selected.
To Date
End date: Check-out

Check availability on Old Town Winter Park Hotels with a Pool

Top Old Town Winter Park Hotels with a Pool

Exterior
Monarch Casino Resort Spa Black Hawk
Monarch Casino Resort Spa Black Hawk
4.0 star property
9.2 out of 10, Wonderful, (4159)
"Great place to stay"
$132 nightly
The price is $157
Oct 19 - Oct 20
Total with taxes and fees
Monarch Casino Resort Spa Black Hawk
Indoor pool, open 7:00 AM to 11:00 PM, sun loungers
Ameristar Casino Resort Spa Black Hawk
Ameristar Casino Resort Spa Black Hawk
4.0 star property
8.6 out of 10, Excellent, (3399)
"Great convenient place to stay."
$106 nightly
The price is $126
Oct 20 - Oct 21
Total with taxes and fees
Ameristar Casino Resort Spa Black Hawk
Indoor pool
Microtel Inn & Suites by Wyndham Georgetown Lake
Microtel Inn & Suites by Wyndham Georgetown Lake
3.0 star property
9.2 out of 10, Wonderful, (1014)
"Great place to stay. "
$117 nightly
The price is $131
Nov 4 - Nov 5
Total with taxes and fees
Microtel Inn & Suites by Wyndham Georgetown Lake
Indoor pool, open 8:30 AM to 9:30 PM, sun loungers
Georgetown Mountain Inn
Georgetown Mountain Inn
2.0 star property
8.6 out of 10, Excellent, (1004)
"Pet friendly rooms with dog park 1 minute away. Very friendly staff."
$88 nightly
The price is $99
Nov 2 - Nov 3
Total with taxes and fees
Georgetown Mountain Inn
Indoor pool
Holiday Inn Express & Suites Fraser - Winter Park Area by IHG
Holiday Inn Express & Suites Fraser - Winter Park Area by IHG
2.5 star property
9.0 out of 10, Wonderful, (1008)
"Nice stay"
$107 nightly
The price is $119
Oct 26 - Oct 27
Total with taxes and fees
Holiday Inn Express & Suites Fraser - Winter Park Area by IHG
Exterior
The Vintage Hotel
The Vintage Hotel
3.0 star property
8.6 out of 10, Excellent, (1010)
"Nice location and very close to alot of restaurants and shopping."
$113 nightly
The price is $128
Oct 27 - Oct 28
Total with taxes and fees
The Vintage Hotel
Outdoor spa tub
Inn at SilverCreek
Inn at SilverCreek
3.0 star property
7.2 out of 10, Good, (1006)
"The staff was extremely friendly and helpful throughout the check-in process, and the room was very nice and clean. Would definitely stay again."
$116 nightly
The price is $123
Oct 15 - Oct 16
Total with taxes and fees
Inn at SilverCreek
Interior
Hiker's Haven / Close to Slopes / Georgetown
Hiker's Haven / Close to Slopes / Georgetown
8.4 out of 10, Very Good, (34)
"Georgetown is the cutest location, and this home was right at the heart. It had all needed amenities, and was perfect for my husband and I. The location was our favorite part!! The bed was super comfy. The carpet has stains, but we understand that the property is used as a rental, so given the price, we weren’t upset by that. "
$339 nightly
The price is $348
Oct 19 - Oct 20
Total with taxes and fees
Hiker's Haven / Close to Slopes / Georgetown
Fridge, microwave, oven, stovetop
The Hollyhock Hideaway / Close to Slopes
The Hollyhock Hideaway / Close to Slopes
9.4 out of 10, Exceptional, (36)
"What a great place that's close to everything! Thanks for a great stay!"
$384 nightly
The price is $395
Oct 20 - Oct 21
Total with taxes and fees
The Hollyhock Hideaway / Close to Slopes
4 bedrooms, iron/ironing board, WiFi, bed sheets
Iconic Log Cabin Escape | Idaho Springs | Hot Tub
Iconic Log Cabin Escape | Idaho Springs | Hot Tub
9.8 out of 10, Exceptional, (35)
"This place was beautiful. Lots of space, a beautiful view and a great location close to town. I will definitely be staying there again when back in town. "
$818 nightly
The price is $880
Oct 29 - Oct 30
Total with taxes and fees
Iconic Log Cabin Escape | Idaho Springs | Hot Tub
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

Top Old Town Winter Park Hotel Reviews

Holiday Inn Express & Suites Fraser - Winter Park Area by IHG

Holiday Inn Express & Suites Fraser - Winter Park Area by IHG

10/10 Excellent
"Hotel is clean and up-to-date. Comfortable rooms. Loved the pool and hot tub. The free breakfast is the best you will find at a hotel! Will definitely stay again. "
Kevin 1-night trip
Posted 1 day ago
Holiday Inn Express & Suites Fraser - Winter Park Area by IHG

Frequently asked questions

What are some accommodations with pools in Old Town Winter Park?
A Frame Club: Resort steps from Ameristar Casino Black Hawk. Offers 5 restaurants, an indoor pool, and a full-service spa. Ameristar Casino Resort Spa Black Hawk: Hotel steps from Monarch Casino Black Hawk. Provides 5 restaurants, an indoor pool, and a full-service spa. Monarch Casino Resort Spa Black Hawk: Hotel located near Winter Park Ski Resort. Features free self parking, a pool, and complimentary wireless internet access. The Vintage Hotel: Offers daily, an indoor pool, and free self parking. Lady Luck Casino Black Hawk: Features 2 outdoor tennis courts, an outdoor pool, and a steam room.
What is there to see and do in Old Town Winter Park?
Explore places like Winter Park Ski Resort while you're in Old Town Winter Park. Make a point to visit attractions like Georgetown Loop Railroad and Amaze'n Maze Winter Park.

Explore a world of travel with Expedia