Holiday rentals near Kennedy Park
We found 363 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals within easy reach of Kennedy Park that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the amenities that you need and want for your stay, which might include a pool and a washer and dryer. At the end of the day, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Kennedy Park
Showing deals for:19 Sept - 26 Sept
Image gallery for COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
9.89.8 out of 10 rating
Exceptional
(159 reviews)
COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
Lee, MA
12% off
Price is AU$2,592
AU$2,592
AU$370 per night
includes taxes & fees
Image gallery for Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee.
1010 out of 10 rating
Exceptional
(22 reviews)
Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee.
Lee, MA
12% off
Price is AU$7,397
AU$7,397
AU$1,057 per night
includes taxes & fees
Image gallery for Secluded Family Home in Serene Stockbridge Woods
1010 out of 10 rating
Exceptional
(21 reviews)
Secluded Family Home in Serene Stockbridge Woods
South Lee, MA
8% off
Price is AU$6,191
AU$6,191
AU$884 per night
includes taxes & fees
Image gallery for Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
9.69.6 out of 10 rating
Exceptional
(97 reviews)
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
Richmond, MA
8% off
Price is AU$3,497
AU$3,497
AU$500 per night
includes taxes & fees
Image gallery for Classic Stockbridge Cottage
1010 out of 10 rating
Exceptional
(15 reviews)
Classic Stockbridge Cottage
Stockbridge, Massachusetts
14% off
Price is AU$4,443
AU$4,443
AU$635 per night
includes taxes & fees
Image gallery for Imagine Being Lakeside This Summer! Book Now!
1010 out of 10 rating
Exceptional
(15 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, Massachusetts
15% off
Price is AU$5,805
AU$5,805
AU$829 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$14,146
AU$14,146
AU$2,021 per night
includes taxes & fees
Image gallery for Renovated Colonial on the River! Fantastic Views
1010 out of 10 rating
Exceptional
(42 reviews)
Renovated Colonial on the River! Fantastic Views
Housatonic, MA
8% off
Price is AU$4,769
AU$4,769
AU$681 per night
includes taxes & fees
Image gallery for Vacation in a Berkshire Farmhouse
9.89.8 out of 10 rating
Exceptional
(89 reviews)
Vacation in a Berkshire Farmhouse
West Stockbridge, MA
11% off
Price is AU$3,908
AU$3,908
AU$558 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
(17 reviews)
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
West Stockbridge, MA
16% off
Price is AU$3,354
AU$3,354
AU$479 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$5,565
AU$5,565
AU$795 per night
includes taxes & fees
Image gallery for Escape to your cozy retreat near Pontoosuc Lake and Jiminy Peak
1010 out of 10 rating
Exceptional
(23 reviews)
Escape to your cozy retreat near Pontoosuc Lake and Jiminy Peak
Pittsfield, MA
8% off
Price is AU$3,729
AU$3,729
AU$533 per night
includes taxes & fees
Image gallery for Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Lee, Massachusetts
9% off
Price is AU$5,478
AU$5,478
AU$783 per night
includes taxes & fees
Image gallery for Stonebridge Cabin: Modern Amenities, Enjoy Nature!
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Stonebridge Cabin: Modern Amenities, Enjoy Nature!
Lee, Massachusetts
15% off
Price is AU$4,372
AU$4,372
AU$625 per night
includes taxes & fees
Image gallery for Woodland Zen by AvantStay | Modern Design + Patio
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Woodland Zen by AvantStay | Modern Design + Patio
Housatonic, Massachusetts
6% off
Price is AU$5,533
AU$5,533
AU$790 per night
includes taxes & fees
Image gallery for Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++
9.49.4 out of 10 rating
Exceptional
(60 reviews)
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++
Lenox, MA
8% off
Price is AU$6,370
AU$6,370
AU$910 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$3,055
AU$3,055
AU$436 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$6,827
AU$6,827
AU$975 per night
includes taxes & fees
Image gallery for Berkshires Lake View, Hot Tub, Large Open Great Room, Lrg Kitchen
1010 out of 10 rating
Exceptional
(6 reviews)
Berkshires Lake View, Hot Tub, Large Open Great Room, Lrg Kitchen
Pittsfield, MA
8% off
Price is AU$5,527
AU$5,527
AU$790 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$4,270
AU$4,270
AU$610 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$5,262
AU$5,262
AU$752 per night
includes taxes & fees
Image gallery for Modern And Spacious Berkshires Retreat 5 bdrm 3 bath
1010 out of 10 rating
Exceptional
(56 reviews)
Modern And Spacious Berkshires Retreat 5 bdrm 3 bath
Lee, MA
12% off
Price is AU$7,320
AU$7,320
AU$1,046 per night
includes taxes & fees
Image gallery for Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
9.29.2 out of 10 rating
Wonderful
(58 reviews)
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
West Stockbridge, MA
12% off
Price is AU$2,921
AU$2,921
AU$417 per night
includes taxes & fees
Image gallery for A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
1010 out of 10 rating
Exceptional
(116 reviews)
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Pittsfield, MA
8% off
Price is AU$3,235
AU$3,235
AU$462 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Kennedy Park
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)
Vacation Village in the Berkshires
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
1,829 reviews(1,829 reviews)
Berkshire Village Carriage House - Super Private!!
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
248 reviews(248 reviews)
Jiminy Peak Mountain Resort
Sleeps 8 · 3 bedrooms
8.28.2 out of 10
Very goodvery good
933 reviews(933 reviews)
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)
Comfortable Berkshires retreat on mtn resort, SISO
Sleeps 12 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 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