Holiday rentals near Deer Leap Trail
We found 1,717 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals close to Deer Leap Trail that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, which might include a garden and pool. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Deer Leap Trail
Showing deals for:29 Aug - 5 Sept
Image gallery for SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF
1010 out of 10 rating
Exceptional
(89 reviews)
SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF
Mount Holly, VT
8% off
Price is NZ$3,865
NZ$3,865
NZ$552 per night
includes taxes & fees
Image gallery for Luxury All Season Belmont Home close to Okemo/Killington , VAST trail & Lakes
1010 out of 10 rating
Exceptional
(8 reviews)
Luxury All Season Belmont Home close to Okemo/Killington , VAST trail & Lakes
Mount Holly, VT
7% off
Price is NZ$18,076
NZ$18,076
NZ$2,582 per night
includes taxes & fees
Image gallery for MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
1010 out of 10 rating
Exceptional
(71 reviews)
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Killington, VT
8% off
Price is NZ$14,463
NZ$14,463
NZ$2,066 per night
includes taxes & fees
Image gallery for MapleDreams - Cozy Ski Chalet w/Hot Tub on Wooded Lot
9.89.8 out of 10 rating
Exceptional
(45 reviews)
MapleDreams - Cozy Ski Chalet w/Hot Tub on Wooded Lot
Stockbridge, VT
8% off
Price is NZ$6,444
NZ$6,444
NZ$921 per night
includes taxes & fees
Image gallery for Beautiful Killington Mountain Views - 2.1 miles to New Killington Base Lodge
1010 out of 10 rating
Exceptional
(33 reviews)
Beautiful Killington Mountain Views - 2.1 miles to New Killington Base Lodge
Killington, VT
16% off
Price is NZ$10,357
NZ$10,357
NZ$1,480 per night
includes taxes & fees
Image gallery for Guest Cabin-- a Mountain Get-Away for Relaxation... or Romance
1010 out of 10 rating
Exceptional
(109 reviews)
Guest Cabin-- a Mountain Get-Away for Relaxation... or Romance
Mount Holly, VT
11% off
Price is NZ$2,355
NZ$2,355
NZ$336 per night
includes taxes & fees
Image gallery for 5 bedroom, 4 bath OKEMO Ski and LAKE Home with A/C
1010 out of 10 rating
Exceptional
(17 reviews)
5 bedroom, 4 bath OKEMO Ski and LAKE Home with A/C
Ludlow, VT
8% off
Price is NZ$15,399
NZ$15,399
NZ$2,200 per night
includes taxes & fees
Image gallery for 🌺Luxury Estate🌳 25 Gorgeous Acres of Privacy 🌳Family Getaway🌳Swimming Pond🌺
9.89.8 out of 10 rating
Exceptional
(12 reviews)
🌺Luxury Estate🌳 25 Gorgeous Acres of Privacy 🌳Family Getaway🌳Swimming Pond🌺
Woodstock, VT
8% off
Price is NZ$14,299
NZ$14,299
NZ$2,043 per night
includes taxes & fees
Image gallery for Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
1010 out of 10 rating
Exceptional
(24 reviews)
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Ludlow, VT
7% off
Price is NZ$16,645
NZ$16,645
NZ$2,378 per night
includes taxes & fees
Image gallery for Alpine Court Chalet: Ultimate Ski-In/Ski-Out Escape at Pico Mountain & Close to Killington.
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Alpine Court Chalet: Ultimate Ski-In/Ski-Out Escape at Pico Mountain & Close to Killington.
Killington, VT
7% off
Price is NZ$4,593
NZ$4,593
NZ$656 per night
includes taxes & fees
Image gallery for Pristine Mountain Farm
1010 out of 10 rating
Exceptional
(26 reviews)
Pristine Mountain Farm
Rochester, VT
19% off
Price is NZ$10,028
NZ$10,028
NZ$1,433 per night
includes taxes & fees
Image gallery for Four Season KILLINGTON Getaway!
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Four Season KILLINGTON Getaway!
Pittsfield, VT
8% off
Price is NZ$4,168
NZ$4,168
NZ$595 per night
includes taxes & fees
Image gallery for Luxury Ski Chalet - Okemo Killington
1010 out of 10 rating
Exceptional
(9 reviews)
Luxury Ski Chalet - Okemo Killington
Ludlow, VT
8% off
Price is NZ$6,325
NZ$6,325
NZ$904 per night
includes taxes & fees
Image gallery for Winter On The Slopes, Summer On The Lake! 3 Br, 2 Baths, Sleeps 8
9.89.8 out of 10 rating
Exceptional
(111 reviews)
Winter On The Slopes, Summer On The Lake! 3 Br, 2 Baths, Sleeps 8
Ludlow, VT
6% off
Price is NZ$5,454
NZ$5,454
NZ$779 per night
includes taxes & fees
Image gallery for Winterplace E building - top of the Quad
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Winterplace E building - top of the Quad
Ludlow, VT
8% off
Price is NZ$18,165
NZ$18,165
NZ$2,595 per night
includes taxes & fees
Image gallery for Private Chalet with Custom WFH Space and Hot Tub
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Private Chalet with Custom WFH Space and Hot Tub
Rutland, VT
12% off
Price is NZ$15,061
NZ$15,061
NZ$2,152 per night
includes taxes & fees
Image gallery for Private House with Fantastic Views off Home Stretch Trail
1010 out of 10 rating
Exceptional
(48 reviews)
Private House with Fantastic Views off Home Stretch Trail
Killington, VT
8% off
Price is NZ$78,058
NZ$78,058
NZ$11,151 per night
includes taxes & fees
Image gallery for Winterplace Condo Steps away from slopes
1010 out of 10 rating
Exceptional
(5 reviews)
Winterplace Condo Steps away from slopes
Ludlow, VT
7% off
Price is NZ$11,706
NZ$11,706
NZ$1,672 per night
includes taxes & fees
Image gallery for Country house minutes from Killington and Okemo
1010 out of 10 rating
Exceptional
(6 reviews)
Country house minutes from Killington and Okemo
Plymouth, VT
8% off
Price is NZ$14,403
NZ$14,403
NZ$2,058 per night
includes taxes & fees
Image gallery for Vermont Trailside Getaway
9.89.8 out of 10 rating
Exceptional
(35 reviews)
Vermont Trailside Getaway
Ludlow, VT
11% off
Price is NZ$3,038
NZ$3,038
NZ$434 per night
includes taxes & fees
Image gallery for "Whispering Pines" Ski House in the heart of the Green Mountains
1010 out of 10 rating
Exceptional
(61 reviews)
"Whispering Pines" Ski House in the heart of the Green Mountains
Stockbridge, VT
8% off
Price is NZ$6,211
NZ$6,211
NZ$887 per night
includes taxes & fees
Image gallery for Luxury 6 BR, 3BA hot tub, deck and yard! Air Conditioning, grill, CEDARWALK
1010 out of 10 rating
Exceptional
(59 reviews)
Luxury 6 BR, 3BA hot tub, deck and yard! Air Conditioning, grill, CEDARWALK
Killington, VT
16% off
Price is NZ$15,905
NZ$15,905
NZ$2,272 per night
includes taxes & fees
Image gallery for As featured in the NY Times: charming, home on Lake Rescue, minutes from Okemo.
9.89.8 out of 10 rating
Exceptional
(74 reviews)
As featured in the NY Times: charming, home on Lake Rescue, minutes from Okemo.
Ludlow, VT
8% off
Price is NZ$5,178
NZ$5,178
NZ$740 per night
includes taxes & fees
Image gallery for Private, All Season 10 Acre Retreat Close to the Slopes, Trails, and Swimming
1010 out of 10 rating
Exceptional
(34 reviews)
Private, All Season 10 Acre Retreat Close to the Slopes, Trails, and Swimming
Plymouth, VT
8% off
Price is NZ$5,855
NZ$5,855
NZ$836 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Deer Leap Trail
Ultimate relaxing vacation
Sleeps 6 · 3 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
191 reviews(191 reviews)
Trail Creek pool/sauna/jacuzzi King, Queen sofa sleep 2Full Baths Two Level Unit
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
123 reviews(123 reviews)
Luxury Trail Creek ski home + shuttle 2king & 3twin beds sauna hot tub end unit
Sleeps 8 · 3 bedrooms · 3+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
85 reviews(85 reviews)
Killington Big House: Largest Vacation Rental in Killington
Sleeps 30 · 12 bedrooms · 10+ bathrooms
1010 out of 10
Exceptionalexceptional
121 reviews(121 reviews)
Spectacular opportunity to enjoy the finest property in Killington Summit
Sleeps 14 · 7 bedrooms · 4 bathrooms
9.49.4 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
Charming 2-bedroom + loft log cabin at Lake Bomoseen in Castleton, Vermont
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 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