Holiday rentals near Skyline Country Club
We found 796 holiday rentals — enter your dates for availability
Discover a selection of private holiday rentals near Skyline Country Club that can be your home away from home. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you expect for your stay, which might include parking and a garden. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Skyline Country Club
Showing deals for:10 Oct - 17 Oct
Image gallery for Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10
1010 out of 10 rating
Exceptional
(6 reviews)
Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge, MA
8% off
Price is AU$14,173
AU$14,173
AU$2,025 per night
includes taxes & fees
Image gallery for Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
1010 out of 10 rating
Exceptional
(11 reviews)
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
Averill Park, NY
8% off
Price is AU$2,715
AU$2,715
AU$388 per night
includes taxes & fees
Image gallery for Charming historic cottage on scenic road to Mt. Greylock
1010 out of 10 rating
Exceptional
(110 reviews)
Charming historic cottage on scenic road to Mt. Greylock
Lanesborough, MA
6% off
Price is AU$2,471
AU$2,471
AU$353 per night
includes taxes & fees
Image gallery for Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hinsdale, MA
8% off
Price is AU$2,098
AU$2,098
AU$300 per night
includes taxes & fees
Image gallery for 1500 sqft private entrance with beautiful views of the Berkshire Mountains
1010 out of 10 rating
Exceptional
(42 reviews)
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Lee, MA
8% off
Price is AU$3,793
AU$3,793
AU$542 per night
includes taxes & fees
Image gallery for General Williams Estate House Lenox/Stockbridge
9.89.8 out of 10 rating
Exceptional
(110 reviews)
General Williams Estate House Lenox/Stockbridge
Stockbridge, MA
8% off
Price is AU$13,997
AU$13,997
AU$2,000 per night
includes taxes & fees
Image gallery for Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.89.8 out of 10 rating
Exceptional
(27 reviews)
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale, MA
12% off
Price is AU$3,623
AU$3,623
AU$518 per night
includes taxes & fees
Image gallery for Cozy cottage with pool, walking distance to lake
1010 out of 10 rating
Exceptional
(15 reviews)
Cozy cottage with pool, walking distance to lake
Averill Park, NY
8% off
Price is AU$3,227
AU$3,227
AU$461 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 AU$4,484
AU$4,484
AU$641 per night
includes taxes & fees
Image gallery for Imagine Being Lakeside This Summer! Book Now!
1010 out of 10 rating
Exceptional
(16 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, Massachusetts
15% off
Price is AU$7,591
AU$7,591
AU$1,084 per night
includes taxes & fees
Image gallery for Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
1010 out of 10 rating
Exceptional
(10 reviews)
Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
Lee, MA
8% off
Price is AU$6,728
AU$6,728
AU$961 per night
includes taxes & fees
Image gallery for Country living close to the capital region 100 acres of nature to explore
1010 out of 10 rating
Exceptional
(5 reviews)
Country living close to the capital region 100 acres of nature to explore
Nassau, NY
7% off
Price is AU$3,662
AU$3,662
AU$523 per night
includes taxes & fees
Image gallery for Berkshire Rural Retreat
1010 out of 10 rating
Exceptional
(21 reviews)
Berkshire Rural Retreat
Canaan, NY
8% off
Price is AU$5,408
AU$5,408
AU$773 per night
includes taxes & fees
Image gallery for Taborton Harvest Boulder Pines Cabin in the woods
1010 out of 10 rating
Exceptional
(11 reviews)
Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake, NY
8% off
Price is AU$1,480
AU$1,480
AU$211 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 AU$5,616
AU$5,616
AU$802 per night
includes taxes & fees
Image gallery for 6-BR Expansive Berkshires Estate w Pool
9.89.8 out of 10 rating
Exceptional
(7 reviews)
6-BR Expansive Berkshires Estate w Pool
Lanesborough, MA
8% off
Price is AU$11,705
AU$11,705
AU$1,672 per night
includes taxes & fees
Image gallery for Beautiful House In The Woods, Huge Yard, Hot Tub
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Beautiful House In The Woods, Huge Yard, Hot Tub
Great Barrington, Massachusetts
16% off
Price is AU$8,883
AU$8,883
AU$1,269 per night
includes taxes & fees
Image gallery for Houghton Hill: Style and History in the Berkshires
1010 out of 10 rating
Exceptional
(9 reviews)
Houghton Hill: Style and History in the Berkshires
North Adams, MA
12% off
Price is AU$4,487
AU$4,487
AU$641 per night
includes taxes & fees
Image gallery for Woodland 5-BR Retreat 5-Min to Jiminy Peak
1010 out of 10 rating
Exceptional
(7 reviews)
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Pittsfield, Massachusetts
8% off
Price is AU$7,042
AU$7,042
AU$1,006 per night
includes taxes & fees
Image gallery for The Maple House - Modern Retreat Near Town
1010 out of 10 rating
Exceptional
(9 reviews)
The Maple House - Modern Retreat Near Town
Lenox, MA
8% off
Price is AU$6,938
AU$6,938
AU$991 per night
includes taxes & fees
Image gallery for A simple kind of paradise
1010 out of 10 rating
Exceptional
(19 reviews)
A simple kind of paradise
Worthington, MA
8% off
Price is AU$2,564
AU$2,564
AU$366 per night
includes taxes & fees
Image gallery for Private river-front home with tennis court and hot tub in the Berkshire hills!
1010 out of 10 rating
Exceptional
(5 reviews)
Private river-front home with tennis court and hot tub in the Berkshire hills!
Cummington, MA
13% off
Price is AU$8,011
AU$8,011
AU$1,144 per night
includes taxes & fees
Image gallery for Private home on a Beautiful lake. Large deck for entertaining
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Private home on a Beautiful lake. Large deck for entertaining
Canaan, NY
8% off
Price is AU$4,957
AU$4,957
AU$708 per night
includes taxes & fees
Image gallery for Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
West Stockbridge, MA
8% off
Price is AU$4,316
AU$4,316
AU$617 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Cottage
Villa
Chalet
Find the best place to stay - Skyline Country Club
Showing deals for: 4 Oct - 7 Oct
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
Sleeps 14 · 6 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
The current price is AU$5,404
AU$5,404
for 3 nights, 1 home
AU$1,801 per night
includes taxes & fees
Vacation Village in the Berkshires
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
1,857 reviews(1,857 reviews)
The current price is AU$576
AU$576
for 3 nights, 1 apartment
AU$192 per night
includes taxes & fees
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
98 reviews(98 reviews)
The current price is AU$1,670
AU$1,670
for 3 nights, 1 home
AU$557 per night
includes taxes & fees
Comfortable Berkshires retreat on mtn resort, SISO
Sleeps 12 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
The current price is AU$2,091
AU$2,091
for 3 nights, 1 home
AU$697 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Sleeps 10 · 4 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
57 reviews(57 reviews)
The current price is AU$3,831
AU$3,831
for 3 nights, 1 home
AU$1,277 per night
includes taxes & fees
Taborton Harvest Boulder Pines Cabin in the woods
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
The current price is AU$730
AU$730
for 3 nights, 1 cabin
AU$243 per night
includes taxes & fees
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