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Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Winter Park vacation rentals

A pool area with lounge chairs and a towel rack, surrounded by a building with a view of a snowy mountain.

1. Walk to Gondola · Alpine Slide & Village

Walk to Gondola · Alpine Slide & Village
Winter Park Village
10.0 out of 10, Exceptional, (93 reviews)
"Great place, super easy short walk to slopes. Would stay again! "
United States
Lee J.
$184 nightly
The price is $206
Nov 13 - Nov 14
Total with taxes and fees
Walk to Gondola · Alpine Slide & Village
A modern living room with a stone fireplace, wooden walls, a large flat-screen TV, a dark wooden entertainment unit, a grey sofa, and a large window with a view of trees.

2. Beaver Village Unit #0332 Remodeled 1 Bedroom vaulted ceiling & private deck

Beaver Village Unit #0332 Remodeled 1 Bedroom vaulted ceiling & private deck
Winter Park
9.2 out of 10, Wonderful, (31 reviews)
"Thoroughly enjoyed our stay. Quite lovely accommodations. Especially enjoyed spa area. Pool, jacuzzi and sauna. Loved hearing the elk bugle outside the windows. Highly recommend and will stay again."
United States
Shannon
$219 nightly
The price is $247
Nov 13 - Nov 14
Total with taxes and fees
Beaver Village Unit #0332 Remodeled 1 Bedroom vaulted ceiling & private deck
A spacious kitchen with wooden cabinets, a granite countertop, and a built-in dishwasher.

3. Beaver Village Unit #2032R Vaulted Ceilings views of Winter Park Resort

Beaver Village Unit #2032R Vaulted Ceilings views of Winter Park Resort
Winter Park
9.6 out of 10, Exceptional, (5 reviews)
"We thoroughly enjoyed our stay. The staff is always friendly and the lodging is exactly what we were looking for."
United States
Dawn C.
$219 nightly
The price is $247
Nov 13 - Nov 14
Total with taxes and fees
Beaver Village Unit #2032R Vaulted Ceilings views of Winter Park Resort
Property grounds

4. Pool Hot Tub Free Garage · Remodeled Studio

Pool Hot Tub Free Garage · Remodeled Studio
Winter Park
9.8 out of 10, Exceptional, (29 reviews)
"Great place , clean and nice. Hot tub and pool were fantastic."
United States
adam d.
$173 nightly
The price is $194
Nov 13 - Nov 14
Total with taxes and fees
Pool Hot Tub Free Garage · Remodeled Studio
Modern mountain resort buildings nestled beside a flowing river, surrounded by evergreen forests and dramatic peaks.

5. Fraser Crossing 3518 remodeled studio gas fireplace and views

Fraser Crossing 3518 remodeled studio gas fireplace and views
Winter Park Village
9.0 out of 10, Wonderful, (19 reviews)
"Everything is good"
United States
Alfonso
$194 nightly
The price is $221
Nov 13 - Nov 14
Total with taxes and fees
Fraser Crossing 3518 remodeled studio gas fireplace and views
A modern building with a hot tub and lounge chairs on a wooden deck.

6. Cozy, 1 bed Condo, 2 Blocks from Downtown, on Bus Rt Short Term License # 004821

Cozy, 1 bed Condo, 2 Blocks from Downtown, on Bus Rt Short Term License # 004821
Winter Park
9.0 out of 10, Wonderful, (62 reviews)
"We came in for a girls weekend getaway and it was hands down the best vrbo experiance ive had. The hosts were so kind and the home was so clean, would definitely book again!"
United States
Mikinzie D.
$207 nightly
The price is $233
Nov 13 - Nov 14
Total with taxes and fees
Cozy, 1 bed Condo, 2 Blocks from Downtown, on Bus Rt Short Term License # 004821
A wooden cabin with a snow-covered porch, surrounded by trees with yellow leaves.

7. Madge’s Studio - Pets Welcome

Madge’s Studio - Pets Welcome
Fraser
10.0 out of 10, Exceptional, (116 reviews)
"We loved our short stay! Very easy to get to where we needed to be and the location is beautiful."
United States
Carrie B.
$139 nightly
The price is $154
Nov 23 - Nov 24
Total with taxes and fees
Madge’s Studio - Pets Welcome
A hotel room with a large bed, a wooden headboard, and a view through a sliding glass door to the outside.

8. Micro Guest Suite Downtown Winter Park GREAT LOCATION

Micro Guest Suite Downtown Winter Park GREAT LOCATION
Winter Park
10.0 out of 10, Exceptional, (23 reviews)
"We enjoyed our stay the room was clean and parking was great and easy. Perfect location! "
United States
Faith R.
$183 nightly
The price is $207
Nov 13 - Nov 14
Total with taxes and fees
Micro Guest Suite Downtown Winter Park GREAT LOCATION
A modern kitchen with wooden cabinets, a built-in island with stools, a flat-screen TV above the island, and a fireplace.

9. Waterside West A303 Ideal and modern 1 bedroom - open floor plan and mt views

Waterside West A303 Ideal and modern 1 bedroom - open floor plan and mt views
Fraser
9.4 out of 10, Exceptional, (16 reviews)
"Great property and location!"
United States
Sarah S.
$213 nightly
The price is $227
Nov 13 - Nov 14
Total with taxes and fees
Waterside West A303 Ideal and modern 1 bedroom - open floor plan and mt views
A multi-story hotel with a ski slope in the background.

10. Zephyr Mountain Lodge

Zephyr Mountain Lodge
3.5 star property
Winter Park Village
8.2 out of 10, Very good, (710 reviews)
"Amazing place to stay and dine."
United States
Carl
$221 nightly
The price is $250
Nov 13 - Nov 14
Total with taxes and fees
Zephyr Mountain Lodge
Dive into the clubhouse indoor oasis, where exposed wood beams frame crystal-clear waters and natural light creates the perfect retreat.

11. Beaver Village Unit #0232R Modern 1 bedroom condo close to downtown & clubhouse

Beaver Village Unit #0232R Modern 1 bedroom condo close to downtown & clubhouse
Winter Park
9.0 out of 10, Wonderful, (6 reviews)
"Great cozy place "
United States
Katherine H.
$219 nightly
The price is $247
Nov 13 - Nov 14
Total with taxes and fees
Beaver Village Unit #0232R Modern 1 bedroom condo close to downtown & clubhouse
Unwind in the cozy clubhouse living room with a crackling fireplace, comfortable leather seating, and warm wood accents perfect for relaxing evenings.

12. Beaver Village Unit #1612R Remodeled king bed and rich leather furnishings

Beaver Village Unit #1612R Remodeled king bed and rich leather furnishings
Winter Park
10.0 out of 10, Exceptional, (5 reviews)
"Cozy little spot perfect for our family of four."
United States
Sean C.
$219 nightly
The price is $247
Nov 13 - Nov 14
Total with taxes and fees
Beaver Village Unit #1612R Remodeled king bed and rich leather furnishings
A spacious living area with a white sofa, a coffee table, and a TV mounted on the wall.

13. Hi Country Haus Unit 1803 1 bedroom, private deck, walk to Main Street

Hi Country Haus Unit 1803 1 bedroom, private deck, walk to Main Street
Winter Park
9.8 out of 10, Exceptional, (24 reviews)
"Great location, super comfortable seating in the living room and the bed was also comfy! Great location in town and near a fun path along the river."
United States
Anonymous traveler
$213 nightly
The price is $240
Nov 14 - Nov 15
Total with taxes and fees
Hi Country Haus Unit 1803 1 bedroom, private deck, walk to Main Street
Sink into plush leather seating at the clubhouse by your crackling fireplace, where warm wood accents create the perfect après-ski retreat.

14. Beaver Village Unit #0412R Wonderful 1 bed unit the perfect mountain getaway!

Beaver Village Unit #0412R Wonderful 1 bed unit the perfect mountain getaway!
Winter Park
10.0 out of 10, Exceptional, (3 reviews)
"Great spot."
United States
Ryan L.
$219 nightly
The price is $247
Nov 13 - Nov 14
Total with taxes and fees
Beaver Village Unit #0412R Wonderful 1 bed unit the perfect mountain getaway!
A building with a sign reading "Founders Pointe."

15. Top Floor Ski-In / Ski-Out Studio Condo at the base of Winter Park Resort

Top Floor Ski-In / Ski-Out Studio Condo at the base of Winter Park Resort
Winter Park Village
9.8 out of 10, Exceptional, (87 reviews)
"Great place, super friendly host! Highly recommend!!"
United States
Tonya T.
$212 nightly
The price is $239
Nov 13 - Nov 14
Total with taxes and fees
Top Floor Ski-In / Ski-Out Studio Condo at the base of Winter Park Resort
A resort with multiple buildings, a swimming pool, and snow-covered surroundings.

16. Meadow Ridge 18-4 Cozy 1 bedroom, ground floor, remodeled, clubhouse amenities

Meadow Ridge 18-4 Cozy 1 bedroom, ground floor, remodeled, clubhouse amenities
Fraser
9.0 out of 10, Wonderful, (10 reviews)
"Great location, very close to town. The pool and tennis courts were great!"
United States
Kami
$219 nightly
The price is $233
Nov 13 - Nov 14
Total with taxes and fees
Meadow Ridge 18-4 Cozy 1 bedroom, ground floor, remodeled, clubhouse amenities
A kitchen with granite countertops, wooden cabinets, and a dining area with a table and chairs.

17. Beaver Village Unit #0931R Located in WP Minutes from Winter Park Resort

Beaver Village Unit #0931R Located in WP Minutes from Winter Park Resort
Winter Park
10.0 out of 10, Exceptional, (3 reviews)
"Beautifully kept condo in a great location!"
United States
Simon M.
$229 nightly
The price is $258
Nov 16 - Nov 17
Total with taxes and fees
Beaver Village Unit #0931R Located in WP Minutes from Winter Park Resort
A glass-bottomed pool surrounded by a metal fence, with snow-covered ground and tall evergreen trees in the background.

18. Newest built Ski-in/Ski-out condos at base of Winter Park

Newest built Ski-in/Ski-out condos at base of Winter Park
Winter Park
9.0 out of 10, Wonderful, (9 reviews)
"Very comfortable room. We had a wonderful stay. Just a few steps outside our door to a ski slope. So convenient and very friendly host. "
United States
MaLinda
$324 nightly
The price is $365
Nov 30 - Dec 1
Total with taxes and fees
Newest built Ski-in/Ski-out condos at base of Winter Park
A wooden interior with a central fireplace, multiple seating areas, and a staircase leading to an upper level.

19. River View Studio Near Winter Park Ski Resort

River View Studio Near Winter Park Ski Resort
Fraser
9.6 out of 10, Exceptional, (4 reviews)
"Very good communication through the entirety of the stay. room is all you really need for one person and it is well maintained. view is great, would stay again. "
United States
Carson
$253 nightly
The price is $280
Nov 18 - Nov 19
Total with taxes and fees
River View Studio Near Winter Park Ski Resort
A living room with a stone fireplace, a television, a sofa with patterned cushions, and a large window overlooking a snowy landscape.

20. Meadow Ridge Court 9 Unit 4 Updated interior in this 1 bedroom, private patio

Meadow Ridge Court 9 Unit 4 Updated interior in this 1 bedroom, private patio
Fraser
9.4 out of 10, Exceptional, (32 reviews)
"We enjoyed our stay"
United States
Caleb M.
$219 nightly
The price is $233
Nov 13 - Nov 14
Total with taxes and fees
Meadow Ridge Court 9 Unit 4 Updated interior in this 1 bedroom, private patio
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.
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Find vacation rentals that suit your style

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Top Winter Park Hotel Reviews

A modern kitchen with dark cabinetry, a central island with stools, a built-in microwave, and a coffee maker.
Winter Park Chateau

Winter Park Chateau

Winter Park Chateau
Winter Park

10/10 Excellent

We had an amazing, relaxing time time. Jon was awesome!
United States
Jessica
Reviewed October 27, 2026
Winter Park Chateau

Find out more about Winter Park

Everything you need to know about Winter Park vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Park vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Park vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Park vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Park. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Park in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $154 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Park rentals

At Expedia, we put the best Winter Park vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Park vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Park. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find vacation rentals in Winter Park?

Yes, we give you a choice of vacation rentals in Winter Park close to Amaze'n Maze Winter Park, or you can select a more remote option if you want a relaxing stay. Visitors like the ski slopes and majestic mountain landscape in Winter Park. You can also check out the live music while you're visiting.

What are some of the best vacation home rentals that Winter Park has to offer?

Creekside Luxury Retreat • 8BR • Walk to Shops, Dining & Shuttle • Sleeps 22: This highly rated vacation home rental in Winter Park is located on the waterfront and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Other favorite homes for rent in Winter Park are Luxury Downtown Condo - Private Hot Tub! Walk to Dining and Ski Bus... and Large Beautiful Townhome, Private Hot Tub, Near Shuttle Route, In Town, WIFI.

How many vacation rentals are there in Winter Park?

With 341 Expedia vacation rentals, you're sure to find just the right place for your Winter Park stay.

What’s there to see and do in Winter Park?

The Fraser River Trail and Arapaho National Recreation Area are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Amaze'n Maze Winter Park. While here, Winter Park Ski Resort and Trestle Bike Park are other places worth a visit.

What’s a vacation rental in Winter Park like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winter Park. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a family trip.

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