Holiday rentals near Hessie Trailhead
We found 3,058 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:25 Jul - 1 Aug
Image gallery for Luxe Winter Park Retreat: Spring Break Special – Shuttle, Hot Tub & Activities
1010 out of 10 rating
Exceptional
(19 reviews)
Luxe Winter Park Retreat: Spring Break Special – Shuttle, Hot Tub & Activities
Fraser, CO
11% off
Price is NZ$12,622
NZ$12,622
NZ$1,803 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$3,678
NZ$3,678
NZ$525 per night
includes taxes & fees
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$8,652
NZ$8,652
NZ$1,236 per night
includes taxes & fees
Image gallery for ~ Central Boulder Gem - Walk to CU/Folsom - 20 acre park out the back gate ~
9.89.8 out of 10 rating
Exceptional
(45 reviews)
~ Central Boulder Gem - Walk to CU/Folsom - 20 acre park out the back gate ~
Boulder, CO
8% off
Price is NZ$8,950
NZ$8,950
NZ$1,279 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
(28 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$4,919
NZ$4,919
NZ$703 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$6,358
NZ$6,358
NZ$908 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$5,349
NZ$5,349
NZ$764 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$13,466
NZ$13,466
NZ$1,924 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$2,889
NZ$2,889
NZ$413 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$17,053
NZ$17,053
NZ$2,436 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$2,421
NZ$2,421
NZ$346 per night
includes taxes & fees
Image gallery for Best downtown location, rooftop deck w private hot tub! 1/2 block to ski shuttle
1010 out of 10 rating
Exceptional
(56 reviews)
Best downtown location, rooftop deck w private hot tub! 1/2 block to ski shuttle
Winter Park, CO
8% off
Price is NZ$12,598
NZ$12,598
NZ$1,800 per night
includes taxes & fees
Image gallery for Stunning Stone Abode in Downtown Boulder - Walk to Pearl St, Chautauqua Park, CU
1010 out of 10 rating
Exceptional
(90 reviews)
Stunning Stone Abode in Downtown Boulder - Walk to Pearl St, Chautauqua Park, CU
Boulder, CO
8% off
Price is NZ$8,270
NZ$8,270
NZ$1,181 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$3,845
NZ$3,845
NZ$549 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$6,080
NZ$6,080
NZ$869 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$20,397
NZ$20,397
NZ$2,914 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$6,272
NZ$6,272
NZ$896 per night
includes taxes & fees
Image gallery for Modern SoBo 3-Bd with Office, Views; Near trails, dining, CU and Chautauqua
1010 out of 10 rating
Exceptional
(27 reviews)
Modern SoBo 3-Bd with Office, Views; Near trails, dining, CU and Chautauqua
Boulder, CO
8% off
Price is NZ$6,519
NZ$6,519
NZ$931 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$5,686
NZ$5,686
NZ$812 per night
includes taxes & fees
Image gallery for Bright & Spacious Cabin 1-mi from Idaho Springs, on 5 acres + Mountain Views!
1010 out of 10 rating
Exceptional
(20 reviews)
Bright & Spacious Cabin 1-mi from Idaho Springs, on 5 acres + Mountain Views!
Idaho Springs, CO
8% off
Price is NZ$8,230
NZ$8,230
NZ$1,176 per night
includes taxes & fees
Image gallery for Beautiful spacious home in heart of Boulder
1010 out of 10 rating
Exceptional
(96 reviews)
Beautiful spacious home in heart of Boulder
Boulder, CO
8% off
Price is NZ$17,550
NZ$17,550
NZ$2,507 per night
includes taxes & fees
Image gallery for Luxury Lakefront Container Home - Sauna, Fishing, Kayaks & Mountain Views
1010 out of 10 rating
Exceptional
(7 reviews)
Luxury Lakefront Container Home - Sauna, Fishing, Kayaks & Mountain Views
Black Hawk, CO
8% off
Price is NZ$8,982
NZ$8,982
NZ$1,283 per night
includes taxes & fees
Image gallery for Beautiful Ski In/Ski Out Studio Condo NO CLEANING FEES
9.89.8 out of 10 rating
Exceptional
(105 reviews)
Beautiful Ski In/Ski Out Studio Condo NO CLEANING FEES
Winter Park, CO
8% off
Price is NZ$2,764
NZ$2,764
NZ$395 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$4,836
NZ$4,836
NZ$691 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
656 reviews(656 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