Holiday rentals near Skyline Country Club
We found 782 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:26 Sept - 3 Oct
Image gallery for 3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome
9.69.6 out of 10 rating
Exceptional
(10 reviews)
3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome
Williamstown, MA
16% off
Price is AU$3,102
AU$3,102
AU$443 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$14,176
AU$14,176
AU$2,025 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
(41 reviews)
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Lee, MA
8% off
Price is AU$3,842
AU$3,842
AU$549 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 AU$6,841
AU$6,841
AU$977 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$2,125
AU$2,125
AU$304 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 AU$3,670
AU$3,670
AU$524 per night
includes taxes & fees
Image gallery for Private Berkshire Cabin on 27acres near Jiminy Peak.
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Private Berkshire Cabin on 27acres near Jiminy Peak.
Williamstown, MA
13% off
Price is AU$3,643
AU$3,643
AU$520 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
8% off
Price is AU$3,655
AU$3,655
AU$522 per night
includes taxes & fees
Image gallery for Amore Estate - beautiful room with many places to explore and relax in.
9.09.0 out of 10 rating
Wonderful
(23 reviews)
Amore Estate - beautiful room with many places to explore and relax in.
Lenox, MA
8% off
Price is AU$11,587
AU$11,587
AU$1,655 per night
includes taxes & fees
Image gallery for Hudson Valley Chalet
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Hudson Valley Chalet
East Chatham, NY
26% off
Price is AU$7,077
AU$7,077
AU$1,011 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$5,813
AU$5,813
AU$830 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$6,814
AU$6,814
AU$973 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$5,273
AU$5,273
AU$753 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$1,499
AU$1,499
AU$214 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$11,222
AU$11,222
AU$1,603 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$5,593
AU$5,593
AU$799 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$3,589
AU$3,589
AU$513 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
15% off
Price is AU$6,719
AU$6,719
AU$960 per night
includes taxes & fees
Image gallery for Cozy Berkshire cottage with fireplace.
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Cozy Berkshire cottage with fireplace.
Pittsfield, MA
8% off
Price is AU$3,062
AU$3,062
AU$437 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$5,513
AU$5,513
AU$788 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
13% off
Price is AU$3,658
AU$3,658
AU$523 per night
includes taxes & fees
Image gallery for Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
Housatonic, Massachusetts
6% off
Price is AU$5,980
AU$5,980
AU$854 per night
includes taxes & fees
Image gallery for Family Fun in The Berkshires at Beautiful Hygge House
1010 out of 10 rating
Exceptional
(10 reviews)
Family Fun in The Berkshires at Beautiful Hygge House
Richmond, MA
8% off
Price is AU$5,577
AU$5,577
AU$797 per night
includes taxes & fees
Image gallery for Secluded Mountaintop Retreat in the Heart of the Berkshires
8.68.6 out of 10 rating
Excellent
(12 reviews)
Secluded Mountaintop Retreat in the Heart of the Berkshires
West Stockbridge, MA
12% off
Price is AU$4,279
AU$4,279
AU$611 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Skyline Country Club
Showing deals for: 22 Sept - 25 Sept
Vacation Village in the Berkshires
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
1,837 reviews(1,837 reviews)
The current price is AU$497
AU$497
for 3 nights, 1 apartment
AU$166 per night
includes taxes & fees
Jiminy Peak Mountain Resort
Sleeps 8 · 3 bedrooms
8.28.2 out of 10
Very goodvery good
937 reviews(937 reviews)
The current price is AU$823
AU$823
for 3 nights, 1 apartment
AU$274 per night
includes taxes & fees
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Sleeps 28 · 8 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
144 reviews(144 reviews)
The current price is AU$2,690
AU$2,690
for 3 nights, 1 home
AU$897 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$1,536
AU$1,536
for 3 nights, 1 home
AU$512 per night
includes taxes & fees
Charming historic cottage on scenic road to Mt. Greylock
Sleeps 5 · 2 bedrooms
1010 out of 10
Exceptionalexceptional
109 reviews(109 reviews)
The current price is AU$1,230
AU$1,230
for 3 nights, 1 cottage
AU$410 per night
includes taxes & fees
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
118 reviews(118 reviews)
The current price is AU$1,502
AU$1,502
for 3 nights, 1 cabin
AU$501 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