Holiday rentals near Skyline Trail
We found 747 holiday rentals — enter your dates for availability
Take a look at private holiday rentals near Skyline Trail that provide the perfect home base for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you need and want for your stay, including Wi-Fi and parking. You're sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Skyline Trail
Showing deals for:1 Aug - 8 Aug
Image gallery for Imagine Being Lakeside This Summer! Book Now!
1010 out of 10 rating
Exceptional
(14 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, Massachusetts
16% off
Price is NZ$19,234
NZ$19,234
NZ$2,748 per night
includes taxes & fees
Image gallery for Summertime at Left Bank Lodge
1010 out of 10 rating
Exceptional
(6 reviews)
Summertime at Left Bank Lodge
Hancock, MA
8% off
Price is NZ$10,463
NZ$10,463
NZ$1,495 per night
includes taxes & fees
Image gallery for Designer Guest Suite on Historic New England Homestead
1010 out of 10 rating
Exceptional
(10 reviews)
Designer Guest Suite on Historic New England Homestead
Florence, MA
12% off
Price is NZ$5,195
NZ$5,195
NZ$742 per night
includes taxes & fees
Image gallery for Ashintully Cottage in spectacular setting
1010 out of 10 rating
Exceptional
(33 reviews)
Ashintully Cottage in spectacular setting
Lee, MA
17% off
Price is NZ$4,449
NZ$4,449
NZ$636 per night
includes taxes & fees
Image gallery for In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
8.68.6 out of 10 rating
Excellent
(10 reviews)
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Hancock, MA
8% off
Price is NZ$3,924
NZ$3,924
NZ$561 per night
includes taxes & fees
Image gallery for Pristine Home In Becket Woods
1010 out of 10 rating
Exceptional
(14 reviews)
Pristine Home In Becket Woods
Becket, Massachusetts
14% off
Price is NZ$4,562
NZ$4,562
NZ$652 per night
includes taxes & fees
Image gallery for Huge Beautiful House-fits 2 families-16 Acres -Low rates- 2 min from Jiminy Peak
9.89.8 out of 10 rating
Exceptional
(68 reviews)
Huge Beautiful House-fits 2 families-16 Acres -Low rates- 2 min from Jiminy Peak
Williamstown, MA
12% off
Price is NZ$5,383
NZ$5,383
NZ$769 per night
includes taxes & fees
Image gallery for Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
Hancock, MA
5% off
Price is NZ$3,692
NZ$3,692
NZ$527 per night
includes taxes & fees
Image gallery for Berkshire Lake at the Pillow, and EV!
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Berkshire Lake at the Pillow, and EV!
Lee, MA
8% off
Price is NZ$5,254
NZ$5,254
NZ$751 per night
includes taxes & fees
Image gallery for Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock, MA
8% off
Price is NZ$2,790
NZ$2,790
NZ$399 per night
includes taxes & fees
Image gallery for Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled
1010 out of 10 rating
Exceptional
(6 reviews)
Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled
Hancock, MA
7% off
Price is NZ$4,848
NZ$4,848
NZ$693 per night
includes taxes & fees
Image gallery for 2 Bedroom Deluxe Condo at Bentley Brook, Jiminy Peak Ski Mountain!!
1010 out of 10 rating
Exceptional
(5 reviews)
2 Bedroom Deluxe Condo at Bentley Brook, Jiminy Peak Ski Mountain!!
Hancock, MA
8% off
Price is NZ$9,547
NZ$9,547
NZ$1,364 per night
includes taxes & fees
Image gallery for 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
9.89.8 out of 10 rating
Exceptional
(7 reviews)
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock, Massachusetts
8% off
Price is NZ$2,790
NZ$2,790
NZ$399 per night
includes taxes & fees
Image gallery for Old World Charm, Modern Conveniences - 3 BR private home in quiet setting
1010 out of 10 rating
Exceptional
(15 reviews)
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting
Easthampton, MA
5% off
Price is NZ$3,760
NZ$3,760
NZ$537 per night
includes taxes & fees
Image gallery for Charming cedar shingle cottage
9.89.8 out of 10 rating
Exceptional
(54 reviews)
Charming cedar shingle cottage
Otis, MA
6% off
Price is NZ$3,890
NZ$3,890
NZ$556 per night
includes taxes & fees
Image gallery for WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
9.29.2 out of 10 rating
Wonderful
(11 reviews)
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock, Massachusetts
8% off
Price is NZ$2,790
NZ$2,790
NZ$399 per night
includes taxes & fees
Image gallery for Cozy Cabin on Lake Mahkeenac
8.88.8 out of 10 rating
Excellent
(10 reviews)
Cozy Cabin on Lake Mahkeenac
West Stockbridge, MA
8% off
Price is NZ$4,170
NZ$4,170
NZ$596 per night
includes taxes & fees
Image gallery for Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock, MA
8% off
Price is NZ$2,790
NZ$2,790
NZ$399 per night
includes taxes & fees
Image gallery for Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
1010 out of 10 rating
Exceptional
(69 reviews)
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock, MA
8% off
Price is NZ$5,729
NZ$5,729
NZ$818 per night
includes taxes & fees
Image gallery for Beautiful Timber Frame Home in the Berkshires /Available for Long Term
1010 out of 10 rating
Exceptional
(19 reviews)
Beautiful Timber Frame Home in the Berkshires /Available for Long Term
Washington, MA
15% off
Price is NZ$5,923
NZ$5,923
NZ$846 per night
includes taxes & fees
Image gallery for Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hinsdale, MA
8% off
Price is NZ$2,308
NZ$2,308
NZ$330 per night
includes taxes & fees
Image gallery for Private apartment in beautiful country barn
1010 out of 10 rating
Exceptional
(18 reviews)
Private apartment in beautiful country barn
Richmond, MA
12% off
Price is NZ$2,637
NZ$2,637
NZ$377 per night
includes taxes & fees
Image gallery for Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
9.69.6 out of 10 rating
Exceptional
(26 reviews)
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock, MA
8% off
Price is NZ$3,765
NZ$3,765
NZ$538 per night
includes taxes & fees
Image gallery for Experience a charming 3 bedroom farm stay close to winter activity.
1010 out of 10 rating
Exceptional
(27 reviews)
Experience a charming 3 bedroom farm stay close to winter activity.
Williamsburg, MA
8% off
Price is NZ$3,371
NZ$3,371
NZ$482 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Skyline Trail
East Otis, MA, Waterfront Summer Cottage, Big Pond,
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sleeps 10 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
East Otis, MA, Waterfront Summer Cottage, Big Pond,
Sleeps 5 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
Sleeps 20 · 6 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
229 reviews(229 reviews)
COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
Sleeps 5 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
156 reviews(156 reviews)
Cozy Cottage on the Lake
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
25 reviews(25 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