Holiday rentals near Skyline Trail
We found 735 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:25 Jul - 1 Aug
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$3,835
NZ$3,835
NZ$548 per night
includes taxes & fees
Image gallery for Secluded Family Home in Serene Stockbridge Woods
1010 out of 10 rating
Exceptional
(20 reviews)
Secluded Family Home in Serene Stockbridge Woods
South Lee, MA
8% off
Price is NZ$7,091
NZ$7,091
NZ$1,013 per night
includes taxes & fees
Image gallery for Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
9.89.8 out of 10 rating
Exceptional
(53 reviews)
Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
Middlefield, MA
12% off
Price is NZ$5,712
NZ$5,712
NZ$816 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$5,396
NZ$5,396
NZ$771 per night
includes taxes & fees
Image gallery for Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
1010 out of 10 rating
Exceptional
(39 reviews)
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Hancock, MA
13% off
Price is NZ$9,157
NZ$9,157
NZ$1,308 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$3,115
NZ$3,115
NZ$445 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$4,699
NZ$4,699
NZ$671 per night
includes taxes & fees
Image gallery for Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
1010 out of 10 rating
Exceptional
(24 reviews)
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale, MA
12% off
Price is NZ$4,024
NZ$4,024
NZ$575 per night
includes taxes & fees
Image gallery for Beautiful Home in AMAZING Berkshire Location
1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful Home in AMAZING Berkshire Location
Lee, MA
8% off
Price is NZ$8,732
NZ$8,732
NZ$1,247 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$3,152
NZ$3,152
NZ$450 per night
includes taxes & fees
Image gallery for Serene Berkshires Home On 5+ Acres, Rustic & Chic
8.88.8 out of 10 rating
Excellent
(6 reviews)
Serene Berkshires Home On 5+ Acres, Rustic & Chic
Otis, Massachusetts
15% off
Price is NZ$8,868
NZ$8,868
NZ$1,267 per night
includes taxes & fees
Image gallery for Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
1010 out of 10 rating
Exceptional
(7 reviews)
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock, Massachusetts
8% off
Price is NZ$3,115
NZ$3,115
NZ$445 per night
includes taxes & fees
Image gallery for Quiet Cabin On Over 12 Acres Of Woods!
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Quiet Cabin On Over 12 Acres Of Woods!
Becket, Massachusetts
15% off
Price is NZ$4,329
NZ$4,329
NZ$618 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$4,148
NZ$4,148
NZ$593 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$3,152
NZ$3,152
NZ$450 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$9,329
NZ$9,329
NZ$1,333 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$3,115
NZ$3,115
NZ$445 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$6,410
NZ$6,410
NZ$916 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$5,892
NZ$5,892
NZ$842 per night
includes taxes & fees
Image gallery for Mountainside Condo Ski In Ski Out
9.09.0 out of 10 rating
Wonderful
(24 reviews)
Mountainside Condo Ski In Ski Out
Hancock, MA
22% off
Price is NZ$1,740
NZ$1,740
NZ$249 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$2,296
NZ$2,296
NZ$328 per night
includes taxes & fees
Image gallery for Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock, MA
8% off
Price is NZ$4,139
NZ$4,139
NZ$591 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
(26 reviews)
Experience a charming 3 bedroom farm stay close to winter activity.
Williamsburg, MA
8% off
Price is NZ$3,381
NZ$3,381
NZ$483 per night
includes taxes & fees
Image gallery for Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Hancock, MA
8% off
Price is NZ$3,115
NZ$3,115
NZ$445 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
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)
The Playhouse: 7k SqFt of Berkshires Modern Luxury & History, 15% OFF MARCH/APR
Sleeps 20 · 6 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
229 reviews(229 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)
Pristine Home In Becket Woods
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
14 reviews(14 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)
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