Book Holiday Homes in South Lee

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in South Lee

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is NZ$410 per night from 14 Jan to 15 Jan
NZ$410
includes taxes & fees
14 Jan - 15 Jan
Stay at this vacation home in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Crane Museum of Papermaking and Crane ...
Berkshire Village Carriage House - Super Private!!
Spectacular views and close to Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy in-room jetted tubs, an in-room coffeemaker, and in-room fireplaces. Popular attractions Lake Mansfield ...
Spectacular views and close to Great Barrington.
Peace and quiet on the lake

Peace and quiet on the lake

Becket
Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and patios. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry are located ...
Peace and quiet on the lake
Save an average of 15% on thousands of hotels when you're signed in
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Ghent
Book a stay at this family-friendly vacation home in Ghent. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Hudson Chatham Winery and ...
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Beautiful Berkshire Farm House on 160+ Acres

Beautiful Berkshire Farm House on 160+ Acres

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Catamount Aerial Adventure Park and ...
Beautiful Berkshire Farm House on 160+ Acres
Private Estate, Heated Yearround Outdoor Pool

Private Estate, Heated Yearround Outdoor Pool

Egremont
Stay at this vacation home in Great Barrington. Enjoy private pools, a garden, and patios. Popular attractions Catamount Aerial Adventure Park and Catamount ...
Private Estate, Heated Yearround Outdoor Pool
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Craryville
The price is NZ$676 per night from 13 Jan to 14 Jan
NZ$676
includes taxes & fees
13 Jan - 14 Jan
Stay at this vacation home in Copake Lake. Enjoy air conditioning. Popular attractions Copake Lake and Mosquito Island are located nearby.
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Lenox
Book a stay at this family-friendly vacation home in Lenox. Enjoy a garden, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Kennedy ...
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

Hillsdale
Book a stay at this family-friendly vacation home in Hillsdale. Enjoy free WiFi, a garden, and patios. Popular attractions High Falls Trail and Community Library ...
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Don't see what you're looking for?
See all available properties in South Lee
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

South Lee Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our South Lee vacation homes are the perfect way for you to wing it.

Holiday houses in South Lee let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of South Lee in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local South Lee adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in South Lee with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of South Lee vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

South Lee Holiday Homes essential information

Accommodation
357 Holiday Homes
Lowest Price
NZ$179
Highest Price
NZ$676
Popular accommodation
Berkshire Village Carriage House - Super Private!!, Spectacular views and close to Great Barrington., Peace and quiet on the lake, Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna, Beautiful Berkshire Farm House on 160+ Acres, Private Estate, Heated Yearround Outdoor Pool, COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!, Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

Top trending hotels in South Lee

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundable
The price is NZ$264 per night from 27 Jan to 28 Jan
NZ$264
includes taxes & fees
27 Jan - 28 Jan
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$179 per night from 13 Jan to 14 Jan
NZ$179
includes taxes & fees
13 Jan - 14 Jan
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Life House Berkshires
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$207 per night from 20 Jan to 21 Jan
NZ$207
includes taxes & fees
20 Jan - 21 Jan
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Yankee, Trademark Collection by Wyndham
Save an average of 15% on thousands of hotels when you're signed in
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is NZ$205 per night from 1 Feb to 2 Feb
NZ$205
includes taxes & fees
1 Feb - 2 Feb
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Don't see what you're looking for?
See all available properties in South Lee
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.