South Lee holiday rentals

We found 619 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:4 Dec - 11 Dec

Living room from back staircase
Interior
View of dining room from living room
Second Floor Bedroom #3 - Master Suite (see floor plans as reference)
Exceptional
(53 reviews)

Beautiful Berkshire Farm House on 160+ Acres

Great Barrington

8% off
AU$9,995
for 7 nights, 1 home
AU$1,428 per night
includes taxes & fees
Beautiful Berkshire Farm House on 160+ Acres
Hot tub overlooking the lake
The great room with wonderful water views and working fireplace
Dining
Sunroom has Queen pull out sofa bed
Exceptional
(86 reviews)

Spectacular setting on your own private lake close to it all!

Lee

8% off
AU$6,417
for 7 nights, 1 home
AU$917 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
Enclosed porch- view into back yard- dining/game table
Kitchen with counter seating for 4- door on the right to garage
Outdoor dining
View from entry into living room- perfect spot for relaxing!
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
AU$5,250
for 7 nights, 1 home
AU$750 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Pool
Terrace/patio
Private kitchen
Games room
Exceptional
(5 reviews)

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

Hillsdale

7% off
AU$7,474
for 7 nights, 1 home
AU$1,068 per night
includes taxes & fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Interior
Terrace/patio
Interior
Exterior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
AU$3,393
for 7 nights, 1 cottage
AU$485 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
Interior
Living area
Exterior detail
Outdoor dining
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
AU$5,831
for 7 nights, 1 home
AU$833 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Dining Room w/ Doors to Screened Porch Dining Area
Fully screened porch!
Reading nook with natural lighting
Kitchen with stainless steel appliances
Exceptional
(7 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Pittsfield

12% off
AU$4,207
for 7 nights, 1 home
AU$601 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Dining
Interior
Exterior
Living area
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,740
for 7 nights, 1 cabin
AU$534 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Outdoor dining and grill on the 16' x 20' wooden deck.
You will love dining and working in this rich and colorful room
A mudroom off the back leads to the large wooden deck
The living room flows into the dining room.
Exceptional
(41 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
AU$4,832
for 7 nights, 1 home
AU$690 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Patio off kitchen
Kitchen
2nd bedroom
Kitchen open to living room
Exceptional
(77 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

New Marlborough

8% off
AU$2,278
for 7 nights, 1 cottage
AU$325 per night
includes taxes & fees
Charming Cottage, New Marlborough Village Green in the Berkshires
Add a touch of warmth and charm to your dining experience!
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
Back patio with Hot Tub
Welcome Home!
Exceptional
(7 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off
AU$7,648
for 7 nights, 1 home
AU$1,093 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Dining room with butcher block table
Terrace/patio
Property grounds
Screened in porch
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
AU$3,719
for 7 nights, 1 home
AU$531 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Private kitchen
Interior
Living area
Pool
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

8% off
AU$4,360
for 7 nights, 1 home
AU$623 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
Living Room
Great Barrington Castle house
Front view of home
Great Barrington Castle
Exceptional
(51 reviews)

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington

8% off
AU$4,893
for 7 nights, 1 home
AU$699 per night
includes taxes & fees
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington
After a hard day on the trails or a long day on the town, relax in this oasis
Never miss a thing with this expansive open concept kitchen and living room
Seamless entertaining with the wide open concept, living room -kitchen- patio
Exceptional
(28 reviews)

Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.

Great Barrington

6% off
AU$5,602
for 7 nights, 1 home
AU$800 per night
includes taxes & fees
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Property grounds
Interior
Kitchen
Kitchen
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
AU$5,351
for 7 nights, 1 home
AU$764 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Alfresco dining
River view from window
dining area
Great room river view
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Stockbridge

8% off
AU$3,497
for 7 nights, 1 home
AU$500 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Outdoor dining
Room
Private kitchen
Private kitchen
Exceptional
(33 reviews)

The Hideaway: Berkshire Home - Village of Egremont

egremont

16% off
AU$3,294
for 7 nights, 1 home
AU$471 per night
includes taxes & fees
The Hideaway: Berkshire Home - Village of Egremont
Exterior
BBQ dinner not included :)
Interior
Interior
Exceptional
(10 reviews)

Family Fun in The Berkshires at Beautiful Hygge House

Pittsfield

8% off
AU$5,014
for 7 nights, 1 home
AU$716 per night
includes taxes & fees
Family Fun in The Berkshires at Beautiful Hygge House
Living area
Interior
Private kitchen
Room
Exceptional
(58 reviews)

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington

12% off
AU$1,639
for 7 nights, 1 apartment
AU$234 per night
includes taxes & fees
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Private kitchen
Outdoor dining
Exterior
Private kitchen
Exceptional
(13 reviews)

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

Monterey

8% off
AU$3,870
for 7 nights, 1 home
AU$553 per night
includes taxes & fees
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Dining Area, view into living room. Games, books, records all available for your enjoyment!
Ultimate Relaxation! The hot tub will be warm and waiting for your arrival
Open floor plan, natural light in a stylish space
Private kitchen
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
AU$3,980
for 7 nights, 1 home
AU$569 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home
view into large bathroom
Dining
Interior
Entry and living room
Exceptional
(16 reviews)

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Richmond

17% off
AU$3,452
for 7 nights, 1 apartment
AU$493 per night
includes taxes & fees
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Exterior
Property grounds
Interior
Room
Wonderful
(6 reviews)

The Serendipity Spot

Great Barrington

7% off
AU$1,959
for 7 nights, 1 apartment
AU$280 per night
includes taxes & fees
The Serendipity Spot

  • 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)
  • Bousquet Ski Area (9.5 mi / 15.3 km)
  • Otis Ridge (10.7 mi / 17.2 km)
  • Catamount Ski Area (12.9 mi / 20.7 km)
  • Kennedy Park (7.1 mi / 11.3 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

Where are the best South Lee ski resort rentals?
For renting ski accommodation near South Lee, Massachusetts, the nearby Butternut Ski Area is a popular choice among travellers. This family-friendly ski resort offers a variety of slopes suitable for all skill levels, and there are several rental properties in the surrounding area. The town of Great Barrington, just a short drive away, provides a range of lodging options from rustic cabins to modern condos. Many of these properties feature amenities such as fully equipped kitchens, cosy living areas with fireplaces, and access to outdoor spaces ideal for après-ski relaxation.In addition to Great Barrington, the town of Lee itself offers charming inns and boutique hotels that cater to skiers. These accommodations often include amenities like ski storage, complimentary breakfast, and indoor pools, making them convenient for those looking to unwind after a day on the slopes. The area is also home to various local shops and restaurants, enhancing the overall experience for visitors.For those interested in exploring beyond the ski runs, the scenic beauty of the Berkshires provides ample opportunities for hiking and winter activities, with many rentals situated close to trails and natural attractions.
What is the most popular type of holiday rental accomodation in South Lee?
In South Lee, apartments are the most popular type of holiday rental, with about 12 available in the area. These apartments are often situated in peaceful neighbourhoods, providing a comfortable and convenient base for exploring the scenic surroundings. Most units feature fully equipped kitchens, cosy living areas, and some may even include outdoor spaces such as balconies or patios.In addition to apartments, there are around 10 holiday houses available, which cater to families or larger groups seeking more space. These homes typically come with multiple bedrooms, fully equipped kitchens, and private gardens, allowing guests to relax and enjoy the outdoors. Several villas, condos, and cottages also offer unique stays, providing a variety of options for visitors to South Lee.
Are there any family house rentals in South Lee?
In South Lee, Massachusetts, there are several family-friendly house rentals available, making it a great spot for family getaways. The town offers a charming atmosphere, with properties often featuring spacious living areas, fully equipped kitchens for family meals, and outdoor spaces for children to play safely. Many homes also come with amenities such as Wi-Fi and air conditioning to ensure comfort during your stay.Visitors can enjoy nearby attractions like the beautiful Lee State Forest or the scenic Stockbridge Bowl, where families can partake in outdoor activities like hiking, swimming, and picnicking. The locale is steeped in natural beauty, providing an ideal backdrop for a memorable family holiday.
Can I rent a holiday home with a pool or hot tub in South Lee?
In South Lee, Massachusetts, there are several holiday homes available for rent that feature pools or hot tubs. This picturesque town, located in the Berkshires, offers a tranquil setting ideal for relaxation. Many properties come equipped with private pools and hot tubs, providing the superb retreat after a day of exploring the beautiful surrounding landscapes.Travellers can expect amenities such as spacious living areas, fully equipped kitchens for self-catering, and outdoor spaces that might include decks or patios for al fresco dining.
Are there pet-friendly house rentals in South Lee?
In South Lee, Massachusetts, there are several pet-friendly house rentals available, offering a wonderful base for those travelling with pets. Many of these accommodations come equipped with amenities such as fully stocked kitchens, outdoor spaces for pets to roam, and comfortable living areas for relaxation after a day of exploration. The region is known for its picturesque landscapes and proximity to outdoor activities, making it an ideal spot for pet owners.Nearby, the beautiful Beartown State Forest provides ample opportunities for hiking and enjoying nature, with trails that are often suitable for pets. Additionally, the charming town atmosphere offers pet-friendly cafes and shops, allowing for a delightful experience for both you and your furry companions.
Are there any remote work holiday rentals in South Lee?
In South Lee, Massachusetts, there are around 32 remote work holiday rentals available, making it a suitable destination for those looking to combine work and leisure. Many of these properties offer essential amenities for remote work, such as free Wi-Fi in rooms and public areas, dedicated desks, and reliable internet service, ensuring a productive environment.The area is known for its beautiful natural surroundings, with nearby attractions like the picturesque Laurel Lake and the scenic Stockbridge Bowl, superb for outdoor activities during breaks from work. Additionally, South Lee is well-placed for exploring the cultural offerings of the Berkshires, including art galleries and local dining establishments. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in South Lee?
In South Lee, popular rental amenities include fully equipped kitchens, allowing guests to prepare their meals comfortably. Many properties also offer onsite parking, which is a convenient feature for those travelling with vehicles. For a cozy atmosphere, fireplaces are commonly found in these rentals, superb for chilly evenings. Additionally, many accommodations come with a deck or patio, providing lovely outdoor spaces for relaxation. Coffee and tea makers are also typical, ensuring that guests can enjoy their morning brews at their leisure.
When is the best time to visit South Lee for a holiday rental?
The best time to visit South Lee for a holiday rental is during the peak season from July to September. This lively period attracts travellers seeking a delightful summer getaway, with plenty of opportunities for outdoor activities, including hiking in the nearby Berkshire Mountains and exploring the picturesque local parks. The warm temperatures, generally ranging from 15 to 30 degrees Celsius, create an ideal environment for sightseeing and enjoying leisurely strolls around the charming town.July stands out as the most popular month, bustling with visitors eager to experience the vibrant setting and partake in various community events. It's a wonderful time for families and friends to gather, as the area offers a range of activities suited to all ages, from cultural festivals to outdoor concerts.If you're looking for a more budget-friendly option, consider visiting in November. This month brings a quieter charm to South Lee, with stunning autumn foliage painting the landscape in vibrant hues. While the weather may be cooler, ranging from 0 to 10 degrees Celsius, it's a great time for peaceful hikes and enjoying the serene beauty of the Berkshires without the crowds.
What are the top attractions in South Lee?
In South Lee, Massachusetts, visitors can enjoy a variety of attractions that showcase the natural beauty and charm of the area. One of the main highlights is the nearby Lee State Forest, which offers hiking trails, picnic areas, and opportunities for birdwatching amidst serene woodland surroundings. The picturesque Laurel Lake is also a popular spot for swimming, fishing, and kayaking, making it a great destination for outdoor enthusiasts.Just a short drive away, the historic town of Stockbridge is home to the Norman Rockwell Museum, where guests can explore the works of the beloved American artist. The town's charming Main Street features quaint shops, galleries, and delightful eateries that reflect the local culture.Additionally, the nearby Tanglewood Music Centre in Lenox hosts summer concerts and events, attracting music lovers from all over. The beautiful grounds provide a stunning backdrop for performances, making it a must-visit for those looking to experience live music in a picturesque setting.
Are all fees included in the South Lee holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any South Lee holiday homes with parking?
Stayz offers a wide selection of holiday homes in South Lee with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for South Lee holiday homes?
You can find great discounts on holiday homes in South Lee on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my South Lee holiday home booking on Stayz?
To find South Lee holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in South Lee?
A long-stay holiday home in South Lee is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a South Lee holiday home?
Book your South Lee holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in South Lee?
Prices for holiday homes in South Lee vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in South Lee to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.