Lee holiday lettings

We found 814 holiday rentals — enter your dates for availability

Discover a selection of 44 homes 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:1 May - 8 May

Image gallery for Luxury Berkshires Retreat in Lenox - Main House & Studio

View of the main house on the left and guest house on the right
10 out of 10, Exceptional, (53 reviews)
Exceptional
(53 reviews)

Luxury Berkshires Retreat in Lenox - Main House & Studio

Lenox

6% off
Price is £7,738
for 7 nights, 1 home
£1,105 per night
includes taxes & fees
Luxury Berkshires Retreat in Lenox - Main House & Studio

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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)
  • Wood's Pond (3 mi / 4.8 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)
  • Wood's Pond (3 mi / 4.8 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)

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 historic downtown area emerges as an excellent choice. This charming neighbourhood is not only picturesque but also offers a delightful array of local shops, cafes, and restaurants, making it a vibrant hub for visitors. Staying here puts you in close proximity to the iconic Lee Premium Outlets, ideal for those looking to indulge in some retail therapy. Additionally, the tranquil beauty of Laurel Lake is just a short drive away, providing a superb spot for swimming, picnicking, or enjoying a leisurely stroll along the water.

Another appealing area is the scenic outskirts of Lee, where the natural beauty of the Berkshires truly shines. This region is superb for those who appreciate outdoor activities, with numerous hiking trails and parks nearby, such as the picturesque October Mountain State Forest. Here, you can immerse yourself in nature while exploring the stunning landscapes that the Berkshires have to offer. While the number of properties may vary, you can generally find a range of holiday rentals in both downtown Lee and its surrounding areas, suiting different preferences and budgets.
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 ski resort rentals near Lee, Massachusetts, the best options can be found in the nearby town of Lenox, which is just a short drive from the popular skiing destination of Jiminy Peak. Lenox offers a range of accommodations, including charming inns, spacious lodges, and private homes. Many properties feature amenities such as fireplaces, hot tubs, and kitchen facilities, great for unwinding after a day on the slopes.

In addition to Lenox, the towns of Great Barrington and Stockbridge also provide convenient access to skiing. Great Barrington has a variety of rental options, from modern condos to rustic cabins, often equipped with comforts like Wi-Fi, outdoor spaces, and access to local dining. Stockbridge, known for its picturesque scenery, offers quaint cottages and larger homes that may include features such as game rooms or expansive gardens.
What is the most popular type of holiday rental accomodation in Lee?
In Lee, holiday houses are the most popular rental option, with around 39 available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for comfort and convenience. Many holiday houses also include outdoor spaces, such as patios or gardens, superb for relaxing after a day of exploring the local attractions, including the picturesque Berkshire Mountains and nearby Tanglewood.
Are there any family house rentals in Lee?
In Lee, Massachusetts, there are numerous family-friendly house rentals available—specifically, around 35 options to choose from. This charming town, situated in the picturesque Berkshires, is ideal for families seeking a blend of outdoor activities and cultural attractions. Many of the properties offer spacious living areas, fully equipped kitchens, and outdoor spaces for children to enjoy. Some homes even include amenities such as game rooms, private gardens, and access to barbecue facilities.
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, providing a refreshing option for travellers seeking relaxation. This picturesque town, located in the Berkshires, offers a variety of amenities within these rentals, including private pools, hot tubs, and spacious outdoor areas ideal for gatherings and family activities. Many properties also come equipped with modern kitchens for self-catering, comfortable living spaces, and easy access to the region's stunning natural beauty.
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 a variety of pet-friendly house rentals available, with around 25 options to choose from. Many of these holiday homes come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups travelling with pets.
Are there any remote work holiday rentals in Lee?
In Lee, Massachusetts, there are numerous remote work holiday rentals available, with around 50 options to choose from. This quaint town, located in the picturesque Berkshires, offers a serene environment ideal for those balancing work and leisure. Many of these properties feature essential remote work amenities such as reliable Wi-Fi, dedicated office spaces, desks, and comfortable chairs, ensuring a productive working atmosphere. 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 rental amenities include well-equipped kitchens, complete with refrigerators, cookware, dishware, utensils, microwaves, and stovetops. These features allow guests to prepare their own meals, making it convenient for families or groups looking to enjoy home-cooked dining during their stay.
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 range of attractions that showcase the area's natural beauty and cultural heritage. The town is near the scenic Laurel Lake, superb for swimming, kayaking, and picnicking during the warmer months. Holiday rentals around this area often provide easy access to the lake, offering a relaxing retreat.

Just a short drive away, the picturesque October Mountain State Forest offers numerous hiking trails and opportunities for outdoor exploration, ideal for those who appreciate nature. For a touch of history, the Lee Premises Historic District features charming architecture and a glimpse into the town's past.
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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