Winterwood holiday rentals

We found 93 holiday rentals — enter your dates for availability

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August 2025

September 2025

Discover a selection of 10 homes and other holiday rentals in Winterwood that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the best amenities for hanging out with the people that matter most, including Wi-Fi and parking. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Winterwood

Showing deals for:14 Nov - 21 Nov

Exceptional

(98 reviews)

Peaceful Forest Getaway with Stunning Views

Breckenridge, CO

7% off

S$480 nightly

Includes taxes & fees

Cozy and private setting with covered parking and huge deck

Exceptional

(56 reviews)

Cozy round house with huge hot tub, 4 bedrooms, sleeps 10 on Peak 7

Breckenridge, CO

8% off

S$588 nightly

Includes taxes & fees

Stainless Steel Appliances with Viking Gas Stove

Exceptional

(50 reviews)

Beautiful Home On 1/2 Acre 2 Miles From Breckenridge 4 bedrm plus study 3.5 Bath

Breckenridge, CO

8% off

S$822 nightly

Includes taxes & fees

Relax on your private deck & BBQ with amazing views!

Exceptional

(55 reviews)

Huge!!|7th Night FREE|Private Hot Tub| 360 Views|Garage|Peak 7|Wildlife|BBQ

Breckenridge, CO

10% off

S$339 nightly

Includes taxes & fees

Find your place on the comfy living room sofa.

Wonderful

(11 reviews)

Ski Breckenridge CO from Peak 7-close to Keystone, Copper Mountain, & A-Basin

Breckenridge, CO

8% off

S$776 nightly

Includes taxes & fees

Main Level Open- Concept Great Room: Perfect for a social atmosphere

Exceptional

(48 reviews)

New constructionChalet on Peak 7 in Breckenridge - 3 miles to Breck Ski Resort

Breckenridge, CO

8% off

S$1,627 nightly

Includes taxes & fees

Exceptional

(69 reviews)

Luxury Home - Jacuzzi, pool table, views of ski runs, next to National Forest

Breckenridge, CO

8% off

S$890 nightly

Includes taxes & fees

Peak 7 Altitude Adjustment! Large Living Room Seating For 10+ Epic Views

Exceptional

(62 reviews)

Do You Like New? Breckenridge Peak 7 - Hot Tub - Sleeps 10

Breckenridge, CO

6% off

S$927 nightly

Includes taxes & fees

Exceptional

(53 reviews)

Luxury Log Cabin Home In Private Mountain Setting Just Minutes To Ski & Town

Breckenridge, CO

8% off

S$746 nightly

Includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Winterwood

Mountain side lives like a 4 bedroom home: 3 bedroom + Bunkroom & 4.5 bathrooms

Sleeps 6 · 3 bedrooms · 3+ bathrooms

New constructionChalet on Peak 7 in Breckenridge - 3 miles to Breck Ski Resort

Sleeps 12 · 5 bedrooms · 4+ bathrooms

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental accommodation in Winterwood?

The most popular types of holiday rentals in Winterwood are houses. Searching for something different? Vrbo has many options to match our guests' unique requirements, so you'll see properties in loads of sizes and shapes. The ideal fit is waiting for you — get yours today.

How much does it cost to rent a holiday rental in Winterwood?

A number of things determine how much you'll pay for a holiday rental in Winterwood, such as the season, type of property and length of stay. However, all our holiday homes have something in common — excellent value. Simply add your travel dates to find your dream escape.

How much does it cost to rent a beach house in Winterwood?

The average price for a holiday rental by the beach in Winterwood depends on when you're travelling and the type and size of property you're looking for. You can easily find prices on Vrbo by entering your preferred travel dates and destination. Then use our filters to choose the number of bedrooms and amenities that you prefer, like WiFi, air conditioning and a hot tub.

Are there pet-friendly holiday rentals in Winterwood?

Yes. There are. You can choose from 12 holiday rentals that allow pets in Winterwood. Lots of our pet-friendly holiday rentals even have an outdoor area for your furry pal to have fun in, complimentary treats, special dog beds and proximity to parks and green space. Apply the "Pets allowed" filter to find your pawfect pad on Vrbo.

What are popular rental amenities in Winterwood?

The most popular rental amenities people are searching for in Winterwood are a nearby river, a firepit and a fireplace. Whether you're taking a trip with family, your besties or even pets, Vrbo holiday properties come with the best amenities for chilling out with the people that matter most.

Are there large group holiday rentals in Winterwood?

Winterwood has three holiday properties that can cater to 10 or more people. These stays come with all the space you need to share good times with family and friends.

Are there holiday rentals in Winterwood that welcome kids?

Bring the whole group together for fun-filled adventures in Winterwood at one of our 12 family-friendly holiday rentals. Lots of these stays feature amenities that are ideal for trips with children, like full kitchens, multiple bedrooms and entertainment units. Simply click on the "Properties good for families" filter and select your favourite.

What are the top attractions for families in Winterwood?

Keeping the kids entertained during your holiday in Winterwood is easy with these leading family-friendly attractions:

Summit Ski Museum
Barney Ford House Museum
Edwin Carter Museum

Are there holiday rentals with WiFi in Winterwood?

Winterwood has six holiday rentals with WiFi, so you'll be able to stay connected during your holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to posting pics on social media, these Vrbo homes will keep you online.

How old do you have to be to rent a holiday rental in Winterwood?

We recommend you check with the Winterwood holiday rental you're looking at on Vrbo as the minimum age differs. However, generally it's 16, 18 or 21.

How long can I rent a holiday rental in Winterwood for?

The length of time you can rent a holiday rental in Winterwood depends on the property. Just enter your desired travel dates to display a list of options offering extended stays. With lots of amenities such as full kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get the perfect place to call your home away from home in Winterwood.