We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Berkshires Luxury Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 mi
Price per night
£0
£1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
45 rentals in Berkshires.
Sort by:
Tripadvisor Sort
Golden Triangle in the Berkshires
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
4 other travellers have booked this property
Walk To Tanglewood, Stocbridge Bowl, Wheatleigh, HTD Pool, Hot Tub, Luxury Home
5 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Deluxe New Home, 2 Master Suites, Tanglewood Area
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
House On Main Street
4 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Turning Point - Family Retreat & Group Getaway
7 bedrooms
8 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Vacation Home on 10 Acres with Pool and Spa
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Lake House
5 bedrooms
6 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
One of the Finest Homes and Best location in the Berkshires
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
Private Berkshire Estate w/Pool & Tennis Court
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Ranch at Fox Hollow - Laurel Lake , 4BR's, 4.5 Baths
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Luxury Fox Hollow Estate Home on Laurel Lake, Hot Tub, Dock with Kayak, Canoe++
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
'Too Good' With 11 Private Acres. Contact us for Monthly Specials!
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
Luxury Fox Hollow Laurel Lake Ranch
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
3 other travellers have booked this property
The perfect Southern Berkshire winter vacation esc
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
NEW LISTING SPECIAL! SAVE 10%! Impeccable House Minutes from Downtown Great Barr
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Gatehouse on Golden Hill. Contact us for Monthly Specials!
4 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Spacious Lakeside Berkshire Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
Designer Loft Style Residence
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Private Home Overlooking Stevens Lake
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beautiful Lakefront Berkshire Rental
5 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Charming Farmhouse on Magical 4 Acre Estate
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
4 other travellers have booked this property
Berkshire Getaway Home with Lake Access
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Shaker Hill
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
3 other travellers have booked this property
Lake House w/ Deck & Views, Mins to Jiminy Peak!
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tanglewood / Berkshires - 2 Bed 2 Bath Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
2 other travellers have booked this property
Luxury Becket Home on 11 Acres W/ Swimming Pond!
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Big Beautiful 7 bedroom 3 bath hot tub pool table
7 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
14 other travellers have booked this property
Comfortable Farmhouse in the Berkshires
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
10 other travellers have booked this property
3BD Newly Rennovated Contempoary Near Stockbridge
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
2 other travellers have booked this property
Newly Renovated Colonial on the River! Sleeps 5-6
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Gem of the Berkshires, walk to downtown & lake.
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
Renovated 2 bedroom in Heart of Lenox
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
Berkshires Spacious Comfortable Charming Farmhouse
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Family-friendly Cottage Near Lake, Tanglewood
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
12 other travellers have booked this property
Family Home w/ Game Room - 3 Miles to Jiminy Peak!
4 bedrooms
3 bathrooms
Sleeps 20
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Escape to the Berkshires!
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
6 other travellers have booked this property
2200sf Country House on 16 Acres-2 Miles to Jiminy
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
3 other travellers have booked this property
Pet-Friendly Berkshires Home w/Dock & Fire Pit!
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Berkshire Farmhouse Vacation
5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
18 other travellers have booked this property
Cozy Modern Condo for the Berkshires
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 other traveller has booked this property
Tranquil 3BR Stockbridge House w/Private Deck
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
3 other travellers have booked this property
PreviousNext
1