Winter Park Vacation Packages 2026 from $803

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The Latest Winter Park Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Landing Chic 2bd, Gym

Devon Park

$803

per person

Jan 7 - Jan 10

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Wilmington (ILM)

4/10 (1 review)

This is a company that I believe sublets an apartment. The place was clean but the coffee maker did not work, the dishwasher would not open and the central heating did not work. These things happen but, we could not get anyone to talk to us or address the issues. Even after the stay I tried several times and several ways to let them know and respond before I posted this. But I still have not heard from anyone. This could not be found.

Reviewed on Oct 19, 2026

Dreamers BNB

Riverfront District

$1,352

per person

Dec 27 - Jan 3

found 13 hours ago

Roundtrip flight included

New York (LGA) to Wilmington (ILM)

9.6/10 Exceptional! (408 reviews)

Perfect location, so walkable to so many restaurants. Beautiful room and house. Would definitely stay here again!

Reviewed on Oct 18, 2026

The Beach House

$982

per person

Dec 27 - Jan 3

found 13 hours ago

Roundtrip flight included

New York (LGA) to Wilmington (ILM)

8.8/10 Excellent! (713 reviews)

This stay is right on the beach! The beds were comfy and we had plenty of towels between the 3 of us. I gave this 4-stars due to the strong smell of wet dog that lingered throughout our stay. I would love to see an upgraded coffee pot/Keurig in the room. Other than that, I would stay again!

Reviewed on Oct 25, 2026

The Sand Dunes

$878

per person

Dec 27 - Jan 3

found 13 hours ago

Roundtrip flight included

New York (LGA) to Wilmington (ILM)

8.8/10 Excellent! (792 reviews)

Loved my stay here. RIght on the beach, friendly staff and close to restaurants!

Reviewed on Oct 25, 2026

Trailborn Surf and Sound, Outdoor Collection by Marriott Bonvoy

$1,428

per person

Dec 27 - Jan 3

found 13 hours ago

Roundtrip flight included

New York (LGA) to Wilmington (ILM)

8.6/10 Excellent! (378 reviews)

This was my first time staying at a Trailborn hotel. Based on my stay, I will always look for Trailborn properties. The restaurant food was great. The bar service, OK. There were a few cocktail orders that were wrong or interesting interpretations. Loved all the amenities (hot tub, sauna, bikes, easy surf board rentals) and the staff was all very nice. The hotel was very leaky when we had a huge rainy day. They only came to clean our room once in 4 days. I was told at check out that I was supposed to request room turnover service at check-in but no one asked me. Overall, minor things that did not distract from a wonderful weekend.

Reviewed on Oct 25, 2026

Where to stay in Winter Park

Find the best Winter Park areas and neighborhoods for the activities you enjoy most. Learn more about Winter Park

A river with a bridge in the background, a dock with boats, and a cityscape on the left.

Downtown Wilmington

2 out of top 10 points of interest in this area

Downtown Wilmington is beloved for its stunning river views. Take some time to explore sights in the area like Wilson Center at Cape Fear Community College and Cape Fear River.

A river with a bridge, a cityscape, and a forested area.

Wilmington Historic District

1 out of top 10 points of interest in this area

Discover a national historic district featuring 875 contributing buildings, Queen Anne and Bungalow/American Craftsman style architecture, and notable landmarks like Bellamy Mansion and St. James Episcopal Church.

Riverfront District

1 out of top 10 points of interest in this area

While visiting Riverfront District, you might make a stop by sights like Wilson Center at Cape Fear Community College and Live Oak Bank Pavilion.

Landfall

While there might not be top attractions in Landfall, you can explore the larger area and discover places like Mayfaire Town Center and Wrightsville SUP.

The Bottom

If you're looking for some top things to see and do in The Bottom and surrounding area, you can visit Brooklyn Arts Center at St. Andrews and Bellamy Mansion Museum.

Winter Park Hotel Deals

Comfort Inn University

151 S College Road Wilmington NC

Fully refundable

$84 nightly

$95 total

Nov 24 - Nov 25

Total with taxes and fees

8.4/10 Very Good! (1,614 reviews)

"The hallway and room had a " odd"smell. Maybe stuffy or old odor. The phone didn't work. Clerk didn't want to honor the reduced price on the website once we arrived. She just said she couldn't because I registered online."

Reviewed on Oct 26, 2026

Shell Island Resort - All Oceanfront Suites

2700 N Lumina Avenue Wrightsville Beach NC

Fully refundableReserve now, pay when you stay

$133 nightly

$151 total

Nov 16 - Nov 17

Total with taxes and fees

8.2/10 Very Good! (1,806 reviews)

"Beautiful ocean views and beach. The property is older, but clean and great location. We would definitely stay there again!"

Reviewed on Oct 25, 2026

Sleep Inn Wilmington near University

5225 Market St Wilmington NC

Fully refundable

$71 nightly

$80 total

Nov 26 - Nov 27

Total with taxes and fees

See all 4,613 properties in Winter Park

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.