Holiday rentals near Skyline Country Club
We found 785 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 NZ$3,367
NZ$3,367
NZ$481 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 NZ$16,048
NZ$16,048
NZ$2,293 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 NZ$4,176
NZ$4,176
NZ$597 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$7,573
NZ$7,573
NZ$1,082 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 NZ$2,269
NZ$2,269
NZ$324 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$3,976
NZ$3,976
NZ$568 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 NZ$3,948
NZ$3,948
NZ$564 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 NZ$3,960
NZ$3,960
NZ$566 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 NZ$12,900
NZ$12,900
NZ$1,843 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
25% off
Price is NZ$7,803
NZ$7,803
NZ$1,115 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 NZ$7,515
NZ$7,515
NZ$1,074 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 NZ$1,589
NZ$1,589
NZ$227 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 NZ$6,298
NZ$6,298
NZ$900 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 NZ$5,721
NZ$5,721
NZ$817 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 NZ$12,562
NZ$12,562
NZ$1,795 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 NZ$3,895
NZ$3,895
NZ$556 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 NZ$6,064
NZ$6,064
NZ$866 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 NZ$7,413
NZ$7,413
NZ$1,059 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 NZ$3,323
NZ$3,323
NZ$475 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 NZ$5,975
NZ$5,975
NZ$854 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 NZ$3,977
NZ$3,977
NZ$568 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 NZ$6,465
NZ$6,465
NZ$924 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 NZ$6,025
NZ$6,025
NZ$861 per night
includes taxes & fees
Image gallery for Charming Farmhouse - quiet, private & peaceful
9.69.6 out of 10 rating
Exceptional
(66 reviews)
Charming Farmhouse - quiet, private & peaceful
Worthington, MA
8% off
Price is NZ$2,664
NZ$2,664
NZ$381 per night
includes taxes & fees
Find spaces that suit your style
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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 NZ$538
NZ$538
for 3 nights, 1 apartment
NZ$179 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 NZ$890
NZ$890
for 3 nights, 1 apartment
NZ$297 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 NZ$2,925
NZ$2,925
for 3 nights, 1 home
NZ$975 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 NZ$1,670
NZ$1,670
for 3 nights, 1 home
NZ$557 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 NZ$1,334
NZ$1,334
for 3 nights, 1 cottage
NZ$445 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
119 reviews(119 reviews)
The current price is NZ$1,722
NZ$1,722
for 3 nights, 1 cabin
NZ$574 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