South Lee holiday homes

We found 615 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in South Lee that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll have the best amenities for spending time at your home away from home, such as Wi-Fi and cable TV. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – South Lee

Showing deals for:27 Nov - 4 Dec

View from entry into living room- perfect spot for relaxing!
Kitchen with counter seating for 4- door on the right to garage
Property grounds
Outdoor dining
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
NZ$6,527
for 7 nights, 1 home
NZ$932 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Exterior detail
Living area
Outdoor dining
Interior
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
NZ$7,101
for 7 nights, 1 home
NZ$1,014 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Games room
Terrace/patio
Property grounds
Pool
Exceptional
(5 reviews)

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale

7% off
NZ$12,111
for 7 nights, 1 home
NZ$1,730 per night
includes taxes & fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Dining
Interior
Property grounds
Living area
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
NZ$4,600
for 7 nights, 1 cabin
NZ$657 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Staircase
You will love dining and working in this rich and colorful room
Outdoor dining and grill on the 16' x 20' wooden deck.
A mudroom off the back leads to the large wooden deck
Exceptional
(41 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
NZ$5,918
for 7 nights, 1 home
NZ$845 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Dining
Terrace/patio
Interior
Interior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
NZ$4,091
for 7 nights, 1 cottage
NZ$584 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
Open kitchen w/ bar & high top seating- sliding door access to second story deck
Open kitchen area with bar seating, great for socializing while you meal prep.
Open and bright main floor living space with stunning views of Laurel Lake.
Living room with fireplace and forest views
Exceptional
(31 reviews)

Lake View Berkshires Retreat - Private & Minutes to Lenox

Lee

16% off
NZ$6,569
for 7 nights, 1 home
NZ$938 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
Welcome Home!
The open-concept living space seamlessly blends the comfort of the living room with the functionality of the kitchen, all adorned by a double sided
Unwind and cherish moments together in the inviting warmth of the cozy living room.
Add a touch of warmth and charm to your dining experience!
Exceptional
(7 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off
NZ$9,659
for 7 nights, 1 home
NZ$1,380 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Queen bedroom
Terrace/patio
Dining room with butcher block table
Screened in porch
Exceptional
(102 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
NZ$4,904
for 7 nights, 1 home
NZ$701 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Kitchen open to living room
Kitchen
Cottage Entrance
2nd  bedroom
Exceptional
(77 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

New Marlborough

8% off
NZ$2,687
for 7 nights, 1 cottage
NZ$384 per night
includes taxes & fees
Charming Cottage, New Marlborough Village Green in the Berkshires
Living area
Interior
Private kitchen
Interior
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

7% off
NZ$5,736
for 7 nights, 1 home
NZ$819 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
Interior
Interior
Property grounds
Kitchen
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
NZ$6,528
for 7 nights, 1 home
NZ$933 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
dining area
River view from window
Great room river view
Alfresco dining
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Stockbridge

8% off
NZ$4,216
for 7 nights, 1 home
NZ$602 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Private kitchen
Interior
Room
Living area
Exceptional
(57 reviews)

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington

12% off
NZ$1,979
for 7 nights, 1 apartment
NZ$283 per night
includes taxes & fees
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Welcome Home!
Ultimate Relaxation!  The hot tub will be warm and waiting for your arrival
Private kitchen
Dining Area, view into living room. Games, books, records all available for your enjoyment!
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
NZ$4,974
for 7 nights, 1 home
NZ$711 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home
Exterior
Property grounds
Interior
Room
Wonderful
(6 reviews)

The Serendipity Spot

Great Barrington

7% off
NZ$2,310
for 7 nights, 1 apartment
NZ$330 per night
includes taxes & fees
The Serendipity Spot
Room
Living area
Private kitchen
Bathroom
Exceptional
(7 reviews)

Comfortable, renovated 2 bedroom apartment in historic grist mill.

SOUTH EGREMONT

16% off
NZ$3,066
for 7 nights, 1 apartment
NZ$438 per night
includes taxes & fees
Comfortable, renovated 2 bedroom apartment in historic grist mill.
Private kitchen
Outdoor dining
Private kitchen
Exterior
Exceptional
(13 reviews)

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

Monterey

8% off
NZ$4,758
for 7 nights, 1 home
NZ$680 per night
includes taxes & fees
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Custom Chef's Kitchen with high end appliances from Bertazzoni and Fisher & Paykel
Private kitchen
Dining
Gorgeous open concept living room
Exceptional
(11 reviews)

The Penthouse, Downtown Lenox by Evergreen Home

Lenox

11% off
NZ$7,796
for 7 nights, 1 apartment
NZ$1,114 per night
includes taxes & fees
The Penthouse, Downtown Lenox by Evergreen Home
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The luxury area of South Lee awaits your stay

Learn about the unique charm of South Lee with a stay in a holiday home rental. This city's restaurants, cheese shops and skiing attract many visitors, as does its romantic and relaxing location. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in South Lee

Are you looking for attractions to visit while you're in the area? Venture out of your holiday home and experience everything that makes South Lee a fun spot to go on holiday. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Wyndhurst Golf & Club (4.5 mi / 7.3 km)
  • Ski Butternut (6.9 mi / 11.1 km)
  • Kennedy Park (7.1 mi / 11.3 km)
  • Bousquet Ski Area (9.5 mi / 15.3 km)
  • Furnace Brook Winery at Hilltop Orchards (9.8 mi / 15.7 km)
  • Otis Ridge (10.7 mi / 17.2 km)

Exploring the natural landscape of South Lee

Whether you're looking for exciting outdoor activities or just want to take in the scenery, South Lee is a great place to get out in nature. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Naumkeag Museum (2.1 mi / 3.5 km)
  • Berkshire Botanical Garden (3.4 mi / 5.5 km)
  • The Mount (4 mi / 6.5 km)
  • Stockbridge Bowl (4.5 mi / 7.2 km)
  • Goose Pond Reservation (4.6 mi / 7.4 km)
  • Lake Mansfield Park (6.8 mi / 10.9 km)

Travelling to and around South Lee

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 10.2 mi (16.4 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.8 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in South Lee?
Based on our research, villas are the most popular type of holiday property in South Lee. But that goes without saying, everyone's idea of an epic trip can differ. Bookabach has holiday homes of all shapes and sizes, so you're sure to discover your perfect match.
How much does it cost to rent a holiday home in South Lee?
The average price for a holiday home in South Lee is based on several factors, like season, length of stay and property type. Whether you prefer a sprawling villa with lots of bedrooms or a cosy cottage for just you and your sweetheart, just add your travel dates to discover stays with amazing value.
How much does it cost to rent a beach house in South Lee?
When you travel and the size and style of the property will influence the cost of your beachside escape. Click on your South Lee travel dates to see all your options on Bookabach. Did someone just say "private pool"? Use the filters to choose the features and amenities you want.
Are there pet-friendly holiday homes in South Lee?
With seven properties that welcome pets, your furry friend can join you on your South Lee break. Use our filter tool to search our pet-friendly holiday homes and find a stay that's pawfect on Bookabach.
Can I rent a house with a pool in South Lee?
Tick the "pool" box in our filter tool and you'll find five houses with private pools in South Lee on Bookabach. Gentle soak, ball games or noodle joust? Leisure time is your call when your Bookabach holiday home comes with its own pool.
What are popular home amenities in South Lee?
When it comes to home amenities that people look for in South Lee, a swimming pool, a sauna and nearby museums are the most popular. With Bookabach holiday homes, you'll enjoy options to fit your taste and style, whether you're holidaying with your partner, your friends or even pets.
Are there large group holiday homes in South Lee?
There are six holiday properties in South Lee that can host a group of five or more guests. From family get-togethers to a special event, these stays have enough room to hang out with the people that matter the most.
Are there holiday homes in South Lee that welcome kids?
South Lee has seven family-friendly holiday homes. And booking a stay that welcomes kids is easy with Bookabach's "Properties good for families" filter. On top of having the whole place to yourselves, you'll also get amenities and perks such as dining rooms, kitchens and pools.
What are the top attractions for families in South Lee?
Keeping the kids amused during your South Lee holiday is a snap with these fabulous family-friendly attractions:
  • Berkshire Scenic Railway Museum
  • Norman Rockwell Museum
  • October Mountain State Forest
Can I find two-bedroom holiday homes in South Lee?
South Lee has three two-bedroom holiday homes to pick from. Find a holiday home with all the space and comfort you want at an attractive price on Bookabach.
Are there holiday homes with WiFi in South Lee?
Choose from three holiday homes with WiFi in South Lee. If you want to disconnect from the world during your trip, but still need to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in South Lee?
South Lee has seven holiday homes where you'll be able to relax and recharge in air-conditioned comfort. To book a stay on Bookabach featuring this perk, choose your travel dates and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in South Lee?
The minimum age is generally 16, 18 or 21. It can vary from property to property on Bookabach, so check the rules of your chosen South Lee holiday home before booking.
How long can I rent a holiday home in South Lee for?
The amount of time you can stay in a South Lee holiday home for is up to each property. Simply put in your travel dates to find available options offering extended stays. They have the things you need to make your extended getaway more convenient and enjoyable, such as kitchens and backyards. Some holiday homes may also offer discounted weekly or monthly prices, so you can stay longer for less money.

More holiday ideas