
Holiday rentals near Hessie Trailhead
We found 3,048 holiday rentals — enter your dates for availability
If you'd like to stay close to Hessie Trailhead, scroll through and discover private holiday rentals to find the perfect one for your trip. Whether you're staying in a holiday rental with family or friends, you'll have the amenities that you expect and more, which might include cable TV and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Hessie Trailhead
Showing deals for:1 Aug - 8 Aug
Image gallery for 4BR Mountain Escape Family Friendly, Sleeps 10

1010 out of 10 rating
Exceptional
(6 reviews)
4BR Mountain Escape Family Friendly, Sleeps 10
Winter Park, Colorado
8% off
Price is NZ$8,578
NZ$8,578
NZ$1,225 per night
includes taxes & fees
Image gallery for Cozy mountain cabin close to hiking/biking, skiing, casinos, good food and more!

9.89.8 out of 10 rating
Exceptional
(24 reviews)
Cozy mountain cabin close to hiking/biking, skiing, casinos, good food and more!
Black Hawk, CO
7% off
Price is NZ$3,680
NZ$3,680
NZ$526 per night
includes taxes & fees
Image gallery for Winter Park Ski in/out XXL ZML condo w/ views of ski hill, gondola, base, river

1010 out of 10 rating
Exceptional
(29 reviews)
Winter Park Ski in/out XXL ZML condo w/ views of ski hill, gondola, base, river
Winter Park, CO
8% off
Price is NZ$4,921
NZ$4,921
NZ$703 per night
includes taxes & fees
Image gallery for Stylish 3 Bedroom/3 Bathroom Near PEARL, PARKS & CU

1010 out of 10 rating
Exceptional
(48 reviews)
Stylish 3 Bedroom/3 Bathroom Near PEARL, PARKS & CU
Boulder, CO
8% off
Price is NZ$13,440
NZ$13,440
NZ$1,920 per night
includes taxes & fees
Image gallery for 4 Bedroom-Private HT. Luxury Escape! Blocks from downtown Winter Park!

1010 out of 10 rating
Exceptional
(8 reviews)
4 Bedroom-Private HT. Luxury Escape! Blocks from downtown Winter Park!
Fraser, CO
8% off
Price is NZ$17,063
NZ$17,063
NZ$2,438 per night
includes taxes & fees
Image gallery for Amazing Views, Family-Friendly 4 Bdrm Boulder Townhome Open Space, 10mns Dntown!

1010 out of 10 rating
Exceptional
(7 reviews)
Amazing Views, Family-Friendly 4 Bdrm Boulder Townhome Open Space, 10mns Dntown!
Boulder, CO
8% off
Price is NZ$5,352
NZ$5,352
NZ$765 per night
includes taxes & fees
Image gallery for Base Camp-Play hard then rest extravagantly! Ski in/out 4 BR-secluded-Jane Creek

1010 out of 10 rating
Exceptional
(113 reviews)
Base Camp-Play hard then rest extravagantly! Ski in/out 4 BR-secluded-Jane Creek
Winter Park, CO
7% off
Price is NZ$13,474
NZ$13,474
NZ$1,925 per night
includes taxes & fees
Image gallery for Boulder Artist Home Mountain Views Garden Pet-Friendly

1010 out of 10 rating
Exceptional
(13 reviews)
Boulder Artist Home Mountain Views Garden Pet-Friendly
Boulder, CO
10% off
Price is NZ$6,416
NZ$6,416
NZ$917 per night
includes taxes & fees
Image gallery for Classic Updated Mapleton Hill historic home! Hike Sanitas, stroll Pearl Street.

1010 out of 10 rating
Exceptional
(11 reviews)
Classic Updated Mapleton Hill historic home! Hike Sanitas, stroll Pearl Street.
Boulder, CO
8% off
Price is NZ$20,409
NZ$20,409
NZ$2,916 per night
includes taxes & fees
Image gallery for Secluded log cabin along serene Hurd Creek ♥

1010 out of 10 rating
Exceptional
(5 reviews)
Secluded log cabin along serene Hurd Creek ♥
Winter Park, CO
7% off
Price is NZ$10,536
NZ$10,536
NZ$1,505 per night
includes taxes & fees
Image gallery for Arapaho Forest Lodge | Hot Tub, Game Room, Hiking

1010 out of 10 rating
Exceptional
(27 reviews)
Arapaho Forest Lodge | Hot Tub, Game Room, Hiking
Black Hawk, CO
9% off
Price is NZ$6,165
NZ$6,165
NZ$881 per night
includes taxes & fees
Image gallery for Amazing Cabin Just Above Downtown Winter Park. Private Hot Tub!

1010 out of 10 rating
Exceptional
(26 reviews)
Amazing Cabin Just Above Downtown Winter Park. Private Hot Tub!
Winter Park, CO
19% off
Price is NZ$6,276
NZ$6,276
NZ$897 per night
includes taxes & fees
Image gallery for 1 BR sleeps 5. Walk to the Gondola! Woods & Fraser River off the back deck.

1010 out of 10 rating
Exceptional
(48 reviews)
1 BR sleeps 5. Walk to the Gondola! Woods & Fraser River off the back deck.
Winter Park, CO
7% off
Price is NZ$2,422
NZ$2,422
NZ$346 per night
includes taxes & fees
Image gallery for GREAT LOCATION! Downtown Winter Park w/Hot Tub! Sleeps 6!

9.69.6 out of 10 rating
Exceptional
(5 reviews)
GREAT LOCATION! Downtown Winter Park w/Hot Tub! Sleeps 6!
Winter Park, CO
7% off
Price is NZ$2,891
NZ$2,891
NZ$413 per night
includes taxes & fees
Image gallery for NEW 3-bdrm in Tabernash w Garage, Fireplace and Office Family and Dog Friendly

1010 out of 10 rating
Exceptional
(5 reviews)
NEW 3-bdrm in Tabernash w Garage, Fireplace and Office Family and Dog Friendly
Tabernash, CO
16% off
Price is NZ$3,747
NZ$3,747
NZ$535 per night
includes taxes & fees
Image gallery for Bike/Hike/Golf/Fish/Beautiful Mountain Views 3BR/3BA

1010 out of 10 rating
Exceptional
(100 reviews)
Bike/Hike/Golf/Fish/Beautiful Mountain Views 3BR/3BA
Granby, CO
7% off
Price is NZ$4,092
NZ$4,092
NZ$585 per night
includes taxes & fees
Image gallery for Walnut Mews - Quiet Creekside townhome next to Pearl Street

1010 out of 10 rating
Exceptional
(140 reviews)
Walnut Mews - Quiet Creekside townhome next to Pearl Street
Boulder, CO
8% off
Price is NZ$8,323
NZ$8,323
NZ$1,189 per night
includes taxes & fees
Image gallery for The Riverside House - Your North Boulder Vacation Retreat

1010 out of 10 rating
Exceptional
(60 reviews)
The Riverside House - Your North Boulder Vacation Retreat
Boulder, CO
8% off
Price is NZ$4,899
NZ$4,899
NZ$700 per night
includes taxes & fees
Image gallery for 3 bed/3 ba Townhouse: hot tub, amazing view and on shuttle route

1010 out of 10 rating
Exceptional
(8 reviews)
3 bed/3 ba Townhouse: hot tub, amazing view and on shuttle route
Winter Park, CO
8% off
Price is NZ$5,689
NZ$5,689
NZ$813 per night
includes taxes & fees
Image gallery for Winter Park Dream Getaway for Large Families - Hot Tub

9.69.6 out of 10 rating
Exceptional
(28 reviews)
Winter Park Dream Getaway for Large Families - Hot Tub
Fraser, CO
8% off
Price is NZ$6,675
NZ$6,675
NZ$954 per night
includes taxes & fees
Image gallery for Modern Condo at Iron Horse - Ski In / Ski Out, Sleeps 4

9.69.6 out of 10 rating
Exceptional
(14 reviews)
Modern Condo at Iron Horse - Ski In / Ski Out, Sleeps 4
Winter Park, CO
8% off
Price is NZ$4,839
NZ$4,839
NZ$691 per night
includes taxes & fees
Image gallery for BEST VIEWS! Luxury Mountain Retreat—Saltwater HotTub/Firepit/BBQ. Close to SKI

1010 out of 10 rating
Exceptional
(14 reviews)
BEST VIEWS! Luxury Mountain Retreat—Saltwater HotTub/Firepit/BBQ. Close to SKI
Evergreen, CO
6% off
Price is NZ$11,250
NZ$11,250
NZ$1,607 per night
includes taxes & fees
Image gallery for Colorado Mountain Getaway Retreat

9.89.8 out of 10 rating
Exceptional
(53 reviews)
Colorado Mountain Getaway Retreat
Idaho Springs, CO
8% off
Price is NZ$4,082
NZ$4,082
NZ$583 per night
includes taxes & fees
Image gallery for Like HOME but BETTER: near Foothills, pvt.apt. in FAB home YOU'LL LOVE IT!

9.49.4 out of 10 rating
Exceptional
(33 reviews)
Like HOME but BETTER: near Foothills, pvt.apt. in FAB home YOU'LL LOVE IT!
Boulder, CO
8% off
Price is NZ$3,285
NZ$3,285
NZ$469 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Hessie Trailhead
11BR Lodge. Rustic space for weddings & retreats! GoCasaVista.
Sleeps 26 · 11 bedrooms · 9+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
74 reviews(74 reviews)
Zephyr Mountain Lodge
Sleeps 4 · 1 bedroom
8.28.2 out of 10
Very goodvery good
657 reviews(657 reviews)
Crestview Lodge at Rocky Mountain Ranch – A Perfect Retreat!
Sleeps 25 · 8 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
9 BDR Home downtown Winter Park, Hot Tub, Shuttle, Sleeps 19!
Sleeps 19 · 9 bedrooms · 6 bathrooms
9.49.4 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
Zephyr Mountain Lodge/Slope Side Bldg True Ski/Bike in/ out with patio walk out
Sleeps 5 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
173 reviews(173 reviews)
Newly renovated Winter Park condo on the Fraser River
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
68 reviews(68 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value