Bailey Vacations 2025 from CA $2,281

Bailey flight + hotel packages

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

Legacy Vacation Resorts - Steamboat Suites

Save 100% on your flight

per person

Feb. 8 - Feb. 15

found 7 hours ago

Roundtrip flight included

Toronto (YYZ) to Denver (DEN)

Stay at this 3-star family-friendly aparthotel in Steamboat Springs. Enjoy free breakfast, free WiFi, and a sauna. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Steamboat Ski Resort and Amaze'n Steamboat Family Fun Park are located nearby.

Aspen Meadows Resort

Save 100% on your flight

per person

Mar. 8 - Mar. 15

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Denver (DEN)

Stay at this 4-star boutique hotel in Aspen. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Buttermilk Mountain and Aspen Mountain are located nearby.

Hotel Jerome, Auberge Resorts Collection

Downtown Aspen

Save 100% on your flight

per person

Mar. 8 - Mar. 15

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Denver (DEN)

Stay at this 5-star luxury hotel in Aspen. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Aspen Mountain and Buttermilk Mountain are located nearby.

Laurelwood Condominiums

Save 100% on your flight

per person

Mar. 8 - Mar. 15

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Denver (DEN)

Stay at this 3-star ski condo in Snowmass Village. Enjoy free WiFi, 2 spa tubs, and a free airport shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Snowmass Mountain and Buttermilk Mountain are located nearby.

The Gant

East Aspen

Save 100% on your flight

per person

Mar. 8 - Mar. 15

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Denver (DEN)

Stay at this 4-star boutique condo in Aspen. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Aspen Mountain and Buttermilk Mountain are located nearby.

Top Bailey hotels deals

Charming A-frame cabin next to stream on 3 acres

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Stay at this cabin in Bailey. Enjoy patios, an in-room coffeemaker, and in-room fireplaces.

Kitchen

Washer

Bailey Lodge

57920 Hwy 285, Bailey, CO

Free cancellation

Reserve now, pay when you stay

CA $133

CA $141 total

includes taxes & fees

5 Jan - 6 Jan 2025

Stay at this hotel in Bailey. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attraction Mount Bailey is located nearby.

Pool

Pet-friendly

Ameristar Casino Resort Spa Black Hawk

111 Richman St, Black Hawk, CO

Free cancellation

Reserve now, pay when you stay

CA $151

CA $200 total

includes taxes & fees

5 Jan - 6 Jan 2025

Stay at this 4-star spa resort in Black Hawk. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ameristar Casino Black Hawk and The Canyon Casino are located nearby.

Pool

Hot tub

Monarch Casino Resort Spa Black Hawk

488 Main St, Black Hawk, CO

CA $187

CA $253 total

includes taxes & fees

23 Dec - 24 Dec

Stay at this 4-star spa hotel in Black Hawk. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the bar in our reviews. Popular attractions Ameristar Casino Black Hawk and Monarch Casino Black Hawk are located nearby.

Pool

Hot tub

Hyatt Vacation Club at The Ranahan

557 Stan Miller Dr, Breckenridge, CO

Free cancellation

CA $938

CA $1,110 total

includes taxes & fees

23 Dec - 24 Dec

Stay at this 4-star ski aparthotel in Breckenridge. Enjoy free WiFi, breakfast (surcharge), and a free ski shuttle. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Breckenridge Ski Resort and Main Street are located nearby.

Pool

Hot tub

Beaver Run Resort & Conference Center

620 Village Rd, Breckenridge, CO

CA $397

CA $472 total

includes taxes & fees

5 Jan - 6 Jan 2025

Stay at this 3.5-star spa resort in Breckenridge. Enjoy free WiFi, a full-service spa, and 8 spa tubs. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Breckenridge Ski Resort and Copper Mountain Ski Resort are located nearby.

Pool

Hot tub

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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.

Popular places to visit

Mount Bailey

Commune with nature and explore the great outdoors at Mount Bailey during your travels in Bailey. Wander the forest or discover the area's mountain views.

Castle Mountain Recreation

Enjoy an outing to Castle Mountain Recreation during your stay in Bailey. Wander the parks or discover the area's mountain views.

McGraw Memorial Park

You can learn about the history of Bailey with a trip to McGraw Memorial Park. Stroll along the riverfront or discover the area's mountain views.

Frequently asked questions

How much are vacation packages to Bailey?

Adventures are calling in Bailey, with Travelocity vacation packages starting from just CA $2,281. Including both hotels and flights, these awesome deals are a simple way to experience more of our wonderful planet.

How long should my Bailey vacation be?

The majority of travelers opt to spend about 3 nights in Bailey, but how long you stay is ultimately up to you. If you intend to get out and explore all the wonderful things this destination offers, why not hang around another few nights?

Where can I get the best vacation package deals for Bailey?

Grabbing the best package deal to Bailey is easy with Travelocity. With 400 partner airlines and 1,000,000 properties worldwide, you’re spoiled for choice when it comes to picking your flights and hotels.

Why should I book my Bailey vacation bundle via Travelocity?

From enticing destinations to fun experiences, we have everything you need to satisfy your travel desires. Our 24/7 customer support will also ensure you’re taken care of before, during and after your vacation. And don’t stress if you find a better price on your reservation, we’ll match it. That’s our Price Match Guarantee.

Can I save money on my Bailey car rental if I combine it with my hotel or flight?

Sure can — combine your car, flight and hotel into a Bailey vacation package and you can save loads. With so much to discover in Bailey, that rental vehicle will more than come in handy. Once you’ve slid into the driver’s seat, put the stereo on and make tracks to Pikes Peak, a renowned attraction approximately 72 kilometers from Bailey.

Which airport is best for Bailey?

Denver Intl. Airport (DEN) is where many tourists touch down. It’s located around 88 kilometers northeast from downtown Bailey. Alternatively, check out the deals to Colorado Springs Airport (COS), which is 97 kilometers away from central Bailey.

What is there to do in Bailey?

There is an undeniable magic as you wander the streets of Bailey. Mount Bailey and Castle Mountain Recreation are just two highlights that make this city so popular, so put them at the top of your list of places to see.

Where should I stay when visiting Bailey?

If you’re after somewhere to spend your nights, check out the Bailey Lodge. It’s the top choice for many travelers.