Holiday rentals near Skylight Pond Trailhead
We found 569 holiday rentals — enter your dates for availability
Take a look at private holiday rentals near Skylight Pond Trailhead that provide the perfect home base for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for spending time at your holiday home, which might include a garden and hot tub. 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 - Skylight Pond Trailhead
Showing deals for:19 Sept - 26 Sept
Image gallery for Pristine Mountain Farm
1010 out of 10 rating
Exceptional
(26 reviews)
Pristine Mountain Farm
Rochester, VT
19% off
Price is NZ$9,984
NZ$9,984
NZ$1,426 per night
includes taxes & fees
Image gallery for Classic Mountain Ski Lodge @ Sugarbush
1010 out of 10 rating
Exceptional
(7 reviews)
Classic Mountain Ski Lodge @ Sugarbush
Warren, VT
8% off
Price is NZ$12,239
NZ$12,239
NZ$1,748 per night
includes taxes & fees
Image gallery for Beautiful 4 Bedroom Home Available this Summer
1010 out of 10 rating
Exceptional
(10 reviews)
Beautiful 4 Bedroom Home Available this Summer
Ripton, VT
12% off
Price is NZ$11,094
NZ$11,094
NZ$1,585 per night
includes taxes & fees
Image gallery for 3 bedroom four season condo one mile from Sugarbush
1010 out of 10 rating
Exceptional
(7 reviews)
3 bedroom four season condo one mile from Sugarbush
Warren, VT
16% off
Price is NZ$4,467
NZ$4,467
NZ$638 per night
includes taxes & fees
Image gallery for NEWLY RENOVATED Private Chic Modern Mountain Home with fiber optic internet!
1010 out of 10 rating
Exceptional
(73 reviews)
NEWLY RENOVATED Private Chic Modern Mountain Home with fiber optic internet!
Warren, VT
8% off
Price is NZ$13,650
NZ$13,650
NZ$1,950 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$7,674
NZ$7,674
NZ$1,096 per night
includes taxes & fees
Image gallery for FAMILY FRIENDLY 4 Season Home for Large Groups, With Hot Tub
9.89.8 out of 10 rating
Exceptional
(12 reviews)
FAMILY FRIENDLY 4 Season Home for Large Groups, With Hot Tub
Roxbury, VT
8% off
Price is NZ$23,496
NZ$23,496
NZ$3,357 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
(62 reviews)
"Whispering Pines" Ski House in the heart of the Green Mountains
Stockbridge, VT
8% off
Price is NZ$6,540
NZ$6,540
NZ$934 per night
includes taxes & fees
Image gallery for Modern luxury home on 40 acres w/ stunning views 15 min. from Sugarbush Ski Area
1010 out of 10 rating
Exceptional
(15 reviews)
Modern luxury home on 40 acres w/ stunning views 15 min. from Sugarbush Ski Area
Waitsfield, VT
8% off
Price is NZ$13,944
NZ$13,944
NZ$1,992 per night
includes taxes & fees
Image gallery for Orchard Cottage - A mountain retreat
1010 out of 10 rating
Exceptional
(78 reviews)
Orchard Cottage - A mountain retreat
Warren, VT
8% off
Price is NZ$4,944
NZ$4,944
NZ$706 per night
includes taxes & fees
Image gallery for Cottage @ Waterhouses
1010 out of 10 rating
Exceptional
(22 reviews)
Cottage @ Waterhouses
Salisbury, VT
12% off
Price is NZ$2,858
NZ$2,858
NZ$408 per night
includes taxes & fees
Image gallery for Vermont Farmhouse in the Heart of the Green Mountains
1010 out of 10 rating
Exceptional
(62 reviews)
Vermont Farmhouse in the Heart of the Green Mountains
Granville, VT
8% off
Price is NZ$4,584
NZ$4,584
NZ$655 per night
includes taxes & fees
Image gallery for Bayou Chalet – Your Perfect Getaway Near Sugarbush Resort
1010 out of 10 rating
Exceptional
(22 reviews)
Bayou Chalet – Your Perfect Getaway Near Sugarbush Resort
Warren, VT
20% off
Price is NZ$4,946
NZ$4,946
NZ$707 per night
includes taxes & fees
Image gallery for The Cabana, a Studio apt. w/ private deck on Lake Dunmore w/ beach. Generator.
1010 out of 10 rating
Exceptional
(37 reviews)
The Cabana, a Studio apt. w/ private deck on Lake Dunmore w/ beach. Generator.
Salisbury, VT
12% off
Price is NZ$2,619
NZ$2,619
NZ$374 per night
includes taxes & fees
Image gallery for Keewaydin Suite @ Waterhouses
9.69.6 out of 10 rating
Exceptional
(23 reviews)
Keewaydin Suite @ Waterhouses
Salisbury, VT
7% off
Price is NZ$3,913
NZ$3,913
NZ$559 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
19% off
Price is NZ$2,347
NZ$2,347
NZ$335 per night
includes taxes & fees
Image gallery for Ski In/Ski out Sugarbush
1010 out of 10 rating
Exceptional
(9 reviews)
Ski In/Ski out Sugarbush
Warren, VT
16% off
Price is NZ$6,163
NZ$6,163
NZ$880 per night
includes taxes & fees
Image gallery for Updated riverfront condo w/deck near MRG/Sugarbush
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Updated riverfront condo w/deck near MRG/Sugarbush
Waitsfield, VT
8% off
Price is NZ$3,711
NZ$3,711
NZ$530 per night
includes taxes & fees
Image gallery for Warren, VT--- Cool & funky guest house at Prickly Mountain
1010 out of 10 rating
Exceptional
(13 reviews)
Warren, VT--- Cool & funky guest house at Prickly Mountain
Warren, VT
7% off
Price is NZ$2,910
NZ$2,910
NZ$416 per night
includes taxes & fees
Image gallery for 2BR Village Run Condo @ Sugarbush/ Lincoln Peak
9.69.6 out of 10 rating
Exceptional
(14 reviews)
2BR Village Run Condo @ Sugarbush/ Lincoln Peak
Warren, VT
12% off
Price is NZ$6,114
NZ$6,114
NZ$873 per night
includes taxes & fees
Image gallery for Sugarbush Ski vacation home, IDEAL proximity to ski resort, Golf & MRV events.
9.89.8 out of 10 rating
Exceptional
(123 reviews)
Sugarbush Ski vacation home, IDEAL proximity to ski resort, Golf & MRV events.
Warren, VT
21% off
Price is NZ$4,552
NZ$4,552
NZ$650 per night
includes taxes & fees
Image gallery for Sun-filled, quiet country home on 27 acres with mountain views
1010 out of 10 rating
Exceptional
(7 reviews)
Sun-filled, quiet country home on 27 acres with mountain views
Middlebury, VT
9% off
Price is NZ$6,728
NZ$6,728
NZ$961 per night
includes taxes & fees
Image gallery for Killington area home - 4-seasons & hot tub. Sleeps 13+
9.89.8 out of 10 rating
Exceptional
(118 reviews)
Killington area home - 4-seasons & hot tub. Sleeps 13+
Pittsfield, VT
11% off
Price is NZ$3,628
NZ$3,628
NZ$518 per night
includes taxes & fees
Image gallery for Mad River Sugarbush Winter and Summer fun Condo -
9.49.4 out of 10 rating
Exceptional
(54 reviews)
Mad River Sugarbush Winter and Summer fun Condo -
Waitsfield, VT
14% off
Price is NZ$4,087
NZ$4,087
NZ$584 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Skylight Pond Trailhead
Showing deals for: 13 Sept - 16 Sept
Cozy Cottage on Beautiful Lake Champlain.
Sleeps 3 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
173 reviews(173 reviews)
The current price is NZ$1,606
NZ$1,606
for 3 nights, 1 cottage
NZ$535 per night
includes taxes & fees
Unplug at Davey Fallls! Water view, Private waterfall & large swimming area.
Sleeps 6 · 1 bedroom · 1+ bathroom
9.09.0 out of 10
Wonderfulwonderful
10 reviews(10 reviews)
The current price is NZ$651
NZ$651
for 3 nights, 1 home
NZ$217 per night
includes taxes & fees
Majestic Lake Champlain Home - 350K in upgrades - Wks in May - Sept 2025 avlbl
Sleeps 12 · 4 bedrooms · 2+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
115 reviews(115 reviews)
The current price is NZ$3,760
NZ$3,760
for 3 nights, 1 home
NZ$1,253 per night
includes taxes & fees
Lake Side Love Nest
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
125 reviews(125 reviews)
The current price is NZ$1,678
NZ$1,678
for 3 nights, 1 cottage
NZ$559 per night
includes taxes & fees
MONKTON LIBRARY COTTAGE
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
The current price is NZ$950
NZ$950
for 3 nights, 1 cottage
NZ$317 per night
includes taxes & fees
Lake Champlain Tiny House on Wooded Property with Private Beach/Lake Access
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
The current price is NZ$2,222
NZ$2,222
for 3 nights, 1 cabin
NZ$741 per night
includes taxes & fees
Top rated rentals - Skylight Pond Trailhead
Perfect Little Getaway!
1010 out of 10
Exceptionalexceptional
19 reviews(19 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