Berkshires Smoking Allowed 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
Neighbourhood
235 rentals in Berkshires.
Sort by:
Tripadvisor Sort
Fox Hollow Laurel Lake Ranch
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Berkshires Home w/Kayak - Walk to Stockbridge Bowl
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Lakefront Berkshires Ski/Summer House, Great Views
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Unique People & Pet-Welcoming Country Haven
1 bedroom
1 bathroom
Sleeps 4
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
Berkshires: Romantic Cottage with spectacular view
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Gartner House, a charming home in Lenox
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Close To Skiing! Beautiful +Family Friendly - W Tree House & Tennis Court
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Berkshire Village Carriage House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Save time - get the best Berkshires rentals sent straight to your email!
Recently renovated 4 bedroom lakefront house in The Berkshires.
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Charming Downtown Williamstown Cottage - 5 Min Walk to Campus
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Antique Farmhouse Totally Restored
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Beautiful 1920's Colonial 20 Minutes from Tanglewood
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Room to Roam. Modern home with all amenities + sep. cabin on 10+ wooded acres.
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Spring Break Special! Stay two nights get one free for March and April!
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Great Barrington Retreat ! Booking for the Fall & Winter Now!
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
5 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
A-Frame in Sherwood Forest
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Lovingly restored Victorian in Lee's Historic District **Spring:3rd nt 1/2 off
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Private rustic cottage with lake access
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
A Grand Estate in Historic Stockbridge
6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Gorgeous Log Cabin in the Berkshires
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
PRIVATE LAKEFRONT BEACH PROPERTY ON GOOSE POND near TANGLEWOOD
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
RANKED #1 for 5 STAR REVIEWS covering 355 properties.
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Elegant 19th Century New England 2BR Vacation Rental at Garfield House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
General Williams Estate House Lenox/Stockbridge
6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Vacation in a Berkshire Farmhouse
5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Tranquil Lake House Getaway on Onota Lake
5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out
Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Beautiful Waterfront home with deep water dock on Onota Lake
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town.
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Berkshire Lake House Vacation Rental
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Retreat in the Woods
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
2 bedroom Riverhouse in the Heart of the Berkshires
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
8 bedrooms
3 bathrooms
Sleeps 21
Match: Sleeps
More info
Check-in
Check-out
Peace And Quiet On The Lake
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Warm your heart this holiday season in this cozy cottage next to downtown Lenox.
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Modern Secluded Home In Wooded Setting
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
5 STAR! Lenox. Luxury. Location.
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Beautiful home with all amenities. Close to everything. Fiber optic internet.
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
19th c. Renovated Barn in the Berkshires
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Charming 1860 Farmhouse, Completely Renovated, Convenient Location, Central AC
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
12345