Lee holiday lettings

We found 839 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:27 Nov - 4 Dec

Open plan dining area with water views and access to the sunroom
view from the 2nd bedroom
View from the lawn by the water
Workstation with a view!
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
£3,698
for 7 nights, 1 home
£528 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
View from entry into living room- perfect spot for relaxing!
Kitchen with counter seating for 4- door on the right to garage
Enclosed porch- view into back yard- dining/game table
Outdoor dining
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
£2,888
for 7 nights, 1 home
£413 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Games room
Terrace/patio
Pool
Private kitchen
Exceptional
(5 reviews)

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

Hillsdale

7% off
£5,083
for 7 nights, 1 home
£726 per night
includes taxes & fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Interior
Living area
Exterior detail
Outdoor dining
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
£3,143
for 7 nights, 1 home
£449 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
A mudroom off the back leads to the large wooden deck
You will love dining and working in this rich and colorful room
The living room flows into the dining room.
Staircase
Exceptional
(41 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
£2,653
for 7 nights, 1 home
£379 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
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
£4,176
for 7 nights, 1 home
£597 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Exterior
Terrace/patio
Dining
Interior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

Great Barrington

8% off
£1,849
for 7 nights, 1 cottage
£264 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
2 car garage—ping pong and bikes.
You, the moon, the fire pit…..,
Flat screen Smart cable tv 5G network. WiFi of course.
It’s cool on the screened porch
Exceptional
(191 reviews)

“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway

Sheffield

8% off
£1,652
for 7 nights, 1 home
£236 per night
includes taxes & fees
“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
kitchen
Brand new hot tub with privacy gazebo. Imagine soaking in this lovely hot tub, where all cares can bubble away.
hot tub and bistro table
Living area
Exceptional
(76 reviews)

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

Sandisfield

7% off
£1,989
for 7 nights, 1 room
£284 per night
includes taxes & fees
A fun country escape for two! featuring a fireplaces,hot tub, and ping pong
Living room with fireplace and forest views
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
£2,871
for 7 nights, 1 home
£410 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
Dining
Interior
Living area
Exterior
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
£2,005
for 7 nights, 1 cabin
£286 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Living area
Private kitchen
Living area
Exterior
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Southfield

8% off
£4,983
for 7 nights, 1 home
£712 per night
includes taxes & fees
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Kitchen
Interior
Property grounds
Interior
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
£2,854
for 7 nights, 1 home
£408 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Alfresco dining
River view from window
Blue House side entry from driveway
Great room river view
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

7% off
£1,905
for 7 nights, 1 home
£272 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Patio off kitchen
Kitchen
Cottage Entrance
Kitchen open to living room
Exceptional
(77 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

Great Barrington

8% off
£1,210
for 7 nights, 1 cottage
£173 per night
includes taxes & fees
Charming Cottage, New Marlborough Village Green in the Berkshires
Private kitchen
Interior
Living area
Pool
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

7% off
£2,555
for 7 nights, 1 home
£365 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
Living room
Property grounds
Coming up the path from down by the creek
Exterior
Exceptional
(11 reviews)

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

Chatham

8% off
£1,320
for 7 nights, 1 home
£189 per night
includes taxes & fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Interior
Living area
Living area
Lobby
Exceptional
(7 reviews)

The Race Mountain House

Sheffield

35% off
£2,833
for 7 nights, 1 home
£405 per night
includes taxes & fees
The Race Mountain House
Screened in porch
Terrace/patio
Queen bedroom
Property grounds
Exceptional
(102 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
£2,133
for 7 nights, 1 home
£305 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
We highly recommend the Sauna
Property grounds
After a day in the snow
Interior
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

11% off
£1,861
for 7 nights, 1 home
£266 per night
includes taxes & fees
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Game, puzzle and play table - plenty of chairs.
Porch opens up from dining room. Ceiling fan and lights above.
Come and unwind.
Entrance view.
Exceptional
(42 reviews)

Converted Berkshire schoolhouse on a quiet river

Great Barrington

8% off
£1,537
for 7 nights, 1 home
£220 per night
includes taxes & fees
Converted Berkshire schoolhouse on a quiet river
Private kitchen
Interior
Room
Exterior
Exceptional
(57 reviews)

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington

12% off
£904
for 7 nights, 1 apartment
£129 per night
includes taxes & fees
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
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
Welcome Home!
Open floor plan, natural light in a stylish space
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

10% off
£2,203
for 7 nights, 1 home
£315 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home
Beaver Pond Pool/clubhouse
new backyard table
another view of kitchen
another view of same bedroom as well as makeup table
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Lanesborough

22% off
£2,694
for 7 nights, 1 apartment
£385 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

  • 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, pools, gardens and more

  • More for less

    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)
  • Kennedy Park (5.4 mi / 8.7 km)
  • Bousquet Ski Area (7.8 mi / 12.6 km)
  • Ski Butternut (9.2 mi / 14.7 km)
  • Furnace Brook Winery at Hilltop Orchards (9.4 mi / 15.1 km)
  • Otis Ridge (10.7 mi / 17.1 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)
  • Kennedy Park (5.4 mi / 8.7 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.
How much does it cost to rent a holiday home in Lee?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Lee to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Lee holiday house rentals?
You can find great discounts on house rentals in Lee on Vrbo, 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.
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.
Can I find long-stay holiday rentals in Lee?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
Are there any Lee holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
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.
How early should I book a Lee holiday rental?
Book your Lee holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Lee home rental booking on Vrbo?
To find Lee holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Lee holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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