Lee holiday rentals

We found 842 holiday rentals — enter your dates for availability
Discover a selection of 44 homes, 12 apartments and other holiday rentals in Lee that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for spending time at your holiday home, which might include parking and a washer and dryer. At the end of the day, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Lee

Showing deals for:18 Dec - 25 Dec

Interior
Terrace/patio
Dining
Interior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

Great Barrington

8% off
AU$3,390
for 7 nights, 1 cottage
AU$484 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
View of the lower deck from the sunroom
view from the 2nd bedroom
Open plan dining area with water views and access to the sunroom
Workstation with a view!
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
AU$7,924
for 7 nights, 1 home
AU$1,132 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Hot tub overlooking the lake
The great room with wonderful water views and working fireplace
Dining
Open kitchen to great room, wonderful for cooking and entertaining
Exceptional
(86 reviews)

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

Lee

8% off
AU$6,412
for 7 nights, 1 home
AU$916 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
Kitchen open to living room
Kitchen
Patio off kitchen
2nd bedroom
Exceptional
(78 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

Great Barrington

8% off
AU$2,314
for 7 nights, 1 cottage
AU$331 per night
includes taxes & fees
Charming Cottage, New Marlborough Village Green in the Berkshires
Welcome!
Property grounds
Dining area and small sitting are with flat screen TV. Stairs to second floor
3 season Sunroom
Exceptional
(7 reviews)

Grand Estate w/ Mountain Views by Evergreen Home

Ghent

11% off
AU$9,341
for 7 nights, 1 home
AU$1,334 per night
includes taxes & fees
Grand Estate w/ Mountain Views by Evergreen Home
Property grounds
Private kitchen
Terrace/patio
Exterior
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
AU$7,854
for 7 nights, 1 home
AU$1,122 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Property grounds
House facing lake with deck above, canoe and kayak stored on ground level.
Terrace/patio
Stairway to landing with one LR couch, barstools, kitchen in background
Exceptional
(169 reviews)

4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

Otis

16% off
AU$2,977
for 7 nights, 1 home
AU$425 per night
includes taxes & fees
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
Outdoor dining
Living area
Interior
Exterior detail
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
AU$6,272
for 7 nights, 1 home
AU$896 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Kitchen with stainless steel appliances
Fully screened porch!
Front Staircase
Reading nook with natural lighting
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

12% off
AU$5,094
for 7 nights, 1 home
AU$728 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Property grounds
Interior
Exterior
Dining
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,738
for 7 nights, 1 cabin
AU$534 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
The living room flows into the dining room.
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
(43 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
AU$5,427
for 7 nights, 1 home
AU$775 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Exterior
Private kitchen
Living area
Living area
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Southfield

8% off
AU$8,977
for 7 nights, 1 home
AU$1,282 per night
includes taxes & fees
Luxurious Mountain Retreat - Private 40-Acre Family Haven
hot tub and bistro table
Brand new hot tub with privacy gazebo. Imagine soaking in this lovely hot tub, where all cares can bubble away.
private entrance
Living area
Exceptional
(76 reviews)

A fun country escape for two! featuring a fireplaces,hot tub, and ping pong

Sandisfield

7% off
AU$2,482
for 7 nights, 1 room
AU$355 per night
includes taxes & fees
A fun country escape for two! featuring a fireplaces,hot tub, and ping pong
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.
Second story deck with lake views, dining table for 8, sitting area and grill
Open and bright main floor living space with stunning views of Laurel Lake.
Exceptional
(31 reviews)

Lake View Berkshires Retreat - Private & Minutes to Lenox

Lee

16% off
AU$5,380
for 7 nights, 1 home
AU$769 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
Come and unwind.
Porch opens up from dining room. Ceiling fan and lights above.
Game, puzzle and play table - plenty of chairs.
Entrance view.
Exceptional
(43 reviews)

Converted Berkshire schoolhouse on a quiet river

Great Barrington

8% off
AU$2,812
for 7 nights, 1 home
AU$402 per night
includes taxes & fees
Converted Berkshire schoolhouse on a quiet river
Dining
Outdoor dining
Exterior detail
Private kitchen
Exceptional
(11 reviews)

Berkshires Getaway Walk to Distillery - No Pet Fee!

Sheffield

8% off
AU$3,999
for 7 nights, 1 home
AU$571 per night
includes taxes & fees
Berkshires Getaway Walk to Distillery - No Pet Fee!
Property grounds
Terrace/patio
Dining room with butcher block table
Screened in porch
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

9% off
AU$3,917
for 7 nights, 1 home
AU$560 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Kitchen
Interior
Kitchen
Property grounds
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
AU$5,347
for 7 nights, 1 home
AU$764 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Enjoy a beautiful crisp night under the lights
After a hard day on the trails or a long day on the town, relax in this oasis
Seamless entertaining with the wide open concept, living room -kitchen- patio
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington
Exceptional
(29 reviews)

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

Great Barrington

6% off
AU$6,407
for 7 nights, 1 home
AU$915 per night
includes taxes & fees
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Living area
Living area
Terrace/patio
Living area
Exceptional
(8 reviews)

Modern Log Chalet - 10 acres, views, and a pond!

Chatham

8% off
AU$5,611
for 7 nights, 1 home
AU$802 per night
includes taxes & fees
Modern Log Chalet - 10 acres, views, and a pond!
dining area
River view from window
Alfresco dining
Great room river view
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

8% off
AU$3,798
for 7 nights, 1 home
AU$543 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Lobby
Living area
Living area
Living area
Excellent
(9 reviews)

The Race Mountain House

Sheffield

35% off
AU$5,436
for 7 nights, 1 home
AU$777 per night
includes taxes & fees
The Race Mountain House
Coming up the path from down by the creek
Property grounds
Living room
Exterior
Exceptional
(13 reviews)

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

8% off
AU$2,923
for 7 nights, 1 home
AU$418 per night
includes taxes & fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Living area
Interior
Exterior
Private kitchen
Exceptional
(61 reviews)

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington

12% off
AU$1,638
for 7 nights, 1 apartment
AU$234 per night
includes taxes & fees
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

Travel to scenic Lee

Come and experience Lee and its churches, museums and monuments. Travellers to this scenic city praise the shopping, lake and forests. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Lee

Are you searching for attractions to see in the area? Venture out of your holiday home and experience everything that Lee has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Wyndhurst Golf & Club (2.9 mi / 4.6 km)
  • Bousquet Ski Area (7.8 mi / 12.6 km)
  • Ski Butternut (9.2 mi / 14.7 km)
  • Otis Ridge (10.7 mi / 17.1 km)
  • Catamount Ski Area (15.1 mi / 24.4 km)
  • Jiminy Peak Mountain Resort (17.5 mi / 28.2 km)

Exploring the natural landscape of Lee

Whether you're an adventurous traveller or just want to take in the scenery, Lee is a great place to spend some time outside. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • The Mount (2.8 mi / 4.5 km)
  • Goose Pond Reservation (3.4 mi / 5.5 km)
  • Naumkeag Museum (3.6 mi / 5.8 km)
  • Stockbridge Bowl (4.2 mi / 6.7 km)
  • Berkshire Botanical Garden (4.5 mi / 7.3 km)
  • Lenox Mountain (7.3 mi / 11.8 km)

Transport to and around Lee

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 8.6 mi (13.9 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 23.7 mi (38.2 km) away.

Frequently asked questions

What is the best area to stay in Lee when booking a holiday rental?
When considering a holiday rental in Lee, Massachusetts, the area around the town centre is an excellent choice. This vibrant neighbourhood offers a blend of convenience and charm, making it ideal for visitors. You'll find a variety of properties available, ranging from quaint cottages to more modern accommodations, suiting different tastes and budgets.Staying in the town centre puts you within easy reach of some of Lee's top attractions. One top point of interest is the Lee Premium Outlets, where you can enjoy a delightful shopping experience with a range of brand-name stores. Additionally, the picturesque October Mountain State Forest is nearby, great for those who appreciate outdoor activities such as hiking and enjoying nature.
Where are the best Lee ski resort rentals?
For the best ski resort rentals in Lee, Massachusetts, visitors should consider looking in the nearby areas of Lenox and Stockbridge, which provide convenient access to the slopes at Jiminy Peak, located just a short drive away. In Lenox, you can find a range of charming lodges and cabins, many featuring amenities such as wood-burning stoves, spacious living areas, and well-equipped kitchens, superb for families or groups wanting to enjoy a cozy mountain retreat after a day on the slopes.Stockbridge also offers a selection of holiday homes that combine rustic charm with modern comforts. Properties in this area often include beautiful views of the surrounding hills, outdoor spaces for relaxation, and easy access to local attractions, including the Norman Rockwell Museum. Rentals here may come with features like hot tubs, fireplaces, and access to hiking trails for those looking to explore the stunning Berkshire region outside of skiing.Additionally, the proximity to cultural highlights, including art galleries and fine dining, enhances the appeal of these locations.
What is the most popular type of holiday rental accomodation in Lee?
In Lee, holiday houses are the most popular type of holiday rental, with around 152 available in various neighbourhoods. These homes typically offer spacious interiors with multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or gardens, ideal for families or groups looking to relax after exploring the scenic beauty of the Berkshires. Additionally, there are about 32 apartments available, which provide a more compact and convenient option, often featuring kitchens and comfortable living areas. Cottages and chalets also add to the appeal, with a handful of each providing charming, rustic settings for a peaceful getaway.
Are there any family house rentals in Lee?
In Lee, Massachusetts, there are numerous family-friendly house rentals—about 36 options to choose from. This charming town offers a blend of outdoor activities and cultural experiences, making it a great destination for families. Many properties come equipped with spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces great for children to enjoy. Visitors can also expect essential amenities like Wi-Fi and air conditioning to ensure a comfortable stay.Situated near popular attractions, families can explore the beautiful landscapes of the Berkshires, with opportunities for hiking, biking, and even winter sports nearby. The town is also close to cultural venues, such as the Norman Rockwell Museum and Tanglewood, where families can enjoy music in a picturesque setting.
Can I rent a holiday home with a pool or hot tub in Lee?
In Lee, Massachusetts, there are several holiday homes available for rent that feature pools or hot tubs. This charming town is set in the picturesque Berkshires, offering a superb blend of relaxation and outdoor activities. Many of the rentals come equipped with private pools, hot tubs, and spacious outdoor areas, ideal for unwinding after exploring the local sights.Travellers can expect amenities such as fully equipped kitchens for self-catering, comfortable living spaces, and often access to beautiful gardens or patios.
Are there pet-friendly house rentals in Lee?
In Lee, Massachusetts, there are several pet-friendly house rentals available, offering a range of amenities to accommodate travellers and their furry companions. Many of these properties typically feature spacious living areas, well-equipped kitchens, and outdoor spaces such as decks or gardens, providing a comfortable environment for families or groups.The town is located in the picturesque Berkshires, making it an excellent base for exploring the surrounding natural beauty. Nearby, the Laurel Lake offers opportunities for swimming, fishing, and hiking, while the nearby October Mountain State Forest provides numerous trails for both pets and their owners to enjoy. These outdoor spaces are ideal for walking and enjoying the scenic views that the Berkshires are known for.
Are there any remote work holiday rentals in Lee?
In Lee, Massachusetts, there are numerous remote work holiday rentals available, with around 192 options to choose from. This charming town is well-suited for those looking to combine work and leisure, offering a blend of scenic beauty and modern amenities. Many of these rentals come equipped with essential features such as free Wi-Fi, dedicated work desks, and comfortable seating areas, ensuring a productive environment for remote workers.The area is rich in outdoor activities, making it an attractive destination. Nearby, the picturesque Berkshire Mountains provide ample opportunities for hiking, biking, and enjoying nature. Additionally, the town is close to cultural attractions, including art galleries and local shops, providing a superb balance of work and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Lee?
In Lee, popular holiday rentals typically offer a variety of amenities that enhance the guest experience. Most properties come equipped with kitchens, allowing travellers to prepare their own meals, along with comfortable living spaces featuring fireplaces to create a warm atmosphere. Decks or patios are common, providing outdoor areas for relaxation and enjoying the surrounding scenery. Onsite parking is also a standard feature, making it convenient for those travelling by car. Additionally, many rentals include coffee and tea makers, ensuring guests can enjoy a warm beverage at their leisure.
When is the best time to visit Lee for a holiday rental?
The best time to visit Lee for a holiday rental is during the peak season from June to August, with July being particularly popular among travellers. During these summer months, the area buzzes with activity as visitors flock to enjoy the beautiful outdoor scenery, vibrant festivals, and numerous recreational opportunities, including hiking and exploring the picturesque landscapes of the Berkshires.Temperatures in Lee during this peak season typically range from the mid-teens to low 30s Celsius, creating a comfortable environment for outdoor adventures and sightseeing. Whether you're wandering through the charming downtown area or taking in the stunning views from nearby Mount Greylock, there's plenty to keep you engaged.If you're looking for a more budget-friendly option, consider visiting in November. This quieter month allows you to savour the beauty of the Berkshires without the crowds, and you can enjoy the peaceful atmosphere that the region offers as it transitions into winter.
What are the top attractions in Lee?
In Lee, Massachusetts, visitors can enjoy a variety of attractions that highlight the area's natural beauty and rich history. The town is located in the picturesque Berkshires, making it a great base for exploring the surrounding landscapes. One of the main draws is the nearby October Mountain State Forest, which offers excellent opportunities for hiking, biking, and enjoying the serene environment.In the heart of Lee, you can visit the Lee Premium Outlets, featuring a range of shops for those looking to indulge in some retail therapy. The historic downtown area is charming, with local boutiques, cafes, and restaurants that reflect the small-town atmosphere.Cultural enthusiasts can explore the nearby Norman Rockwell Museum in Stockbridge, which celebrates the work of the iconic American illustrator and is just a short drive away. The area is also known for its vibrant arts scene, with various galleries and performances throughout the Berkshires.For those interested in the outdoors, the nearby Berkshire Botanical Garden offers beautiful landscapes and themed gardens, making it a delightful spot for a leisurely stroll.
Are all fees included in the 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 Lee holiday homes with parking?
Stayz offers a wide selection of holiday homes in 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 Lee holiday homes?
You can find great discounts on holiday homes in 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 Lee holiday home booking on Stayz?
To find 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 Lee?
A long-stay holiday home in 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 Lee holiday home?
Book your 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 Lee?
Prices for holiday homes in 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 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.

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