The Highlands Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Price found within the past 48 hours. Click for updated prices.
The Springs Condominiums by Vail Resorts

The Springs Condominiums by Vail Resorts

River Run
S$1,677
per person
7 Nov - 14 Nov
found 7 hours ago
Return direct flight included
Kelowna (YLW) to Denver (DEN)
7.8/10 Good! (16 reviews)
Great family oriented resort. The kids loved the pool and slide. We appreciated the on-site BBQ. We'll definitely be back for more.

Reviewed on 30 Jun, 2026

River Run Townhomes by Vail Resorts

River Run Townhomes by Vail Resorts

Mountain House
Save 100% on your flight
S$3,593
per person
7 Nov - 14 Nov
found 7 hours ago
Return direct flight included
Kelowna (YLW) to Denver (DEN)
8.6/10 Excellent! (7 reviews)
The townhome was beautiful and it was walking distance to everything we needed. There was plenty of room for my family of four to spread out and have our own spaces. The only thing I would complain about is the directions to check in sent us to the wrong location.

Reviewed on 6 Jan, 2023

Timbers & Lone Eagle by Vail Resorts

Timbers & Lone Eagle by Vail Resorts

River Run
S$1,715
per person
7 Nov - 14 Nov
found 7 hours ago
Return direct flight included
Kelowna (YLW) to Denver (DEN)
9.2/10 Wonderful! (65 reviews)
Wish we had stayed longer than one night. Great location, clean property, and great amenities.

Reviewed on 2 Aug, 2026

Jackpine & Black Bear Condos by Vail Resorts

Jackpine & Black Bear Condos by Vail Resorts

River Run
S$1,684
per person
7 Nov - 14 Nov
found 7 hours ago
Return direct flight included
Kelowna (YLW) to Denver (DEN)
9/10 Wonderful! (40 reviews)
Located next to Ink Spot, great coffee/food.

Reviewed on 26 Sept, 2026

Expedition Station Condos by Vail Resorts

Expedition Station Condos by Vail Resorts

River Run
Save 100% on your flight
S$2,254
per person
7 Nov - 14 Nov
found 7 hours ago
Return direct flight included
Kelowna (YLW) to Denver (DEN)
9.8/10 Exceptional! (12 reviews)

Where to stay in The Highlands

Find the best The Highlands areas and neighborhoods for the activities you enjoy most. Learn more about The Highlands
A street with a green-roofed building, parked cars, and outdoor seating with yellow umbrellas.

Historic District

3 out of top 10 points of interest in this area

The picture-perfect mountain views and popular ski slopes are top of the list for many visitors to Historic District. A stop by Breckenridge Ski Resort or Quandary Antiques Cabin & Ceramic Studio might round out your trip.

Find hotels in Historic District
A snow-covered mountainous landscape with a town nestled in the valley.

Peak 9

3 out of top 10 points of interest in this area

The picture-perfect mountain views and popular ski slopes are top of the list for many visitors to Peak 9. A stop by Breckenridge Ski Resort or Peak 8 SuperConnect Lift might round out your trip.

Find hotels in Peak 9
A snow-covered mountain range with a clear blue sky.

Peak 8

Unique features of Peak 8 include the skiing and mountain views. Make a stop by Breckenridge Ski Resort or Four O'Clock Ski Run while you're exploring the area.

Find hotels in Peak 8
A snow-covered mountain range with dense forests and clear skies.

Four O'Clock

1 out of top 10 points of interest in this area

The captivating mountain views and stunning ski slopes are top of the list for many visitors to Four O'Clock. A stop by Breckenridge Ski Resort or Snowflake Chair Lift might round out your trip.

Find hotels in Four O'Clock
A snow-covered mountain range with a town at its base, illuminated by artificial lights.

Peak 7

1 out of top 10 points of interest in this area

If you're spending some time in Peak 7, Breckenridge Ski Resort and Breckenridge Nordic Center are top sights worth seeing.

Find hotels in Peak 7

Top hotels in The Highlands

Hyatt Vacation Club at The Ranahan

Hyatt Vacation Club at The Ranahan

557 Stan Miller Dr Breckenridge CO
Fully refundableReserve now, pay when you stay
S$176
25 Oct - 26 Oct
includes taxes & fees
Hyatt Vacation Club at The Ranahan
Keystone Lodge & Spa, A Vail Resorts Property

Keystone Lodge & Spa, A Vail Resorts Property

22101 US Highway 6 Keystone CO
Fully refundableReserve now, pay when you stay
S$206
4 Oct - 5 Oct
includes taxes & fees
Keystone Lodge & Spa, A Vail Resorts Property
Beaver Run Resort & Conference Center

Beaver Run Resort & Conference Center

620 Village Rd Breckenridge CO
S$244
1 Nov - 2 Nov
includes taxes & fees
Beaver Run Resort & Conference Center
See all 12,864 properties in The Highlands
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.

Frequently asked questions

How much does a The Highlands holiday package cost?
Starting from as low as S$1,677, a package is your portal to cheaper travel. Custom make your The Highlands adventure by selecting from our wide range of airfares, hotels and rental cars.
How do I get a cheap travel package to The Highlands?
One of the simplest ways to save cash (and time) is to combine your bookings with Expedia. Flights, hotels, activities and rental cars — we've got everything you need. Select the combination that best suits you and see your savings stack up. We know a travel package is never one-size-fits-all. That's why we offer more than 550 partner airlines and 1,000,000 properties throughout the world, which lets you customize your The Highlands getaway.
Where should I stay in The Highlands?
With lots to explore in The Highlands, we suggest you lock in a hotel near its attractions. Breckenridge Riverwalk Centre, BreckConnect Gondola and Breckenridge Golf Club are some good ones to add to your to-do list.
What are the top hotels in The Highlands?
If it's your first time in The Highlands, lock in a room at Remodeled 2 Level Condo With A Fireplace or Tasteful Mountain Abode: 3 Mi To Breckenridge. Both hotels offer comfortable beds and are popular options with many travellers.
How far in advance should I book my The Highlands holiday?
It depends on the air carrier, but you can usually browse through international flights on Expedia up to a year in advance. While it's generally recommended to book ahead of time, lucky travellers occasionally score a cheaper flight only weeks before their intended journey.
What does an Expedia The Highlands travel package include?
From hotels and airfares to rental cars, Expedia can help you shape a The Highlands package that fits you. Heading off for a few weeks? Consider a hotel, rental car and flight bundle. If you're taking a quick break, a hotel and airfare deal may suit you better. Experiences can also be added once you've made your booking. Our holiday packages make it easy to plan and save.
What should I know before booking a The Highlands travel package?
A package can be more affordable than individually booking all you need for your trip. For example, bundle your hotels, flights and rental cars and score big savings. Whatever your holiday plans, you'll find a package to suit your budget.
Can I choose my airline with a The Highlands Expedia holiday package?
Most definitely. Expedia has over 550 partner airlines to select from globally. With so many choices, finding the right carrier to bring you to The Highlands will be a snap.
If I'm not able to travel, can I cancel my The Highlands holiday package?
You sure can, and we'll help you every step of the way. You may be able to cancel or change your The Highlands holiday package for free if you booked in the last 24 hours. But you may incur a fee from your airline, hotel or car rental company for older bookings. If your circumstances unexpectedly change, browse our Customer Service Portal for further information.

Stay near popular The Highlands attractions

Breckenridge Golf Club

8.8/10 (18 reviews)
Play a round of golf in Breckenridge at Breckenridge Golf Club, and enjoy other activities such as skiing. Wander the lakeside or discover the area's mountain views.
See properties

Things to do

Continental Divide Tour

Continental Divide Tour

S$221
per adult
Continental Divide Tour
Breckenridge: E-Bike Rental with Long-Range Battery

Breckenridge: E-Bike Rental with Long-Range Battery

S$100
per adult
Breckenridge: E-Bike Rental with Long-Range Battery
Fat Tire E Bike Rental in Breckenridge Delivered to you

Fat Tire E Bike Rental in Breckenridge

S$108
per adult
Fat Tire E Bike Rental in Breckenridge
See all activities in Breckenridge

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.