Best Vacation Homes in Lee
1500 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $312/Night
For 7 Nights CA $2,183
1506.95 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- View
- Pet Friendly
CA $624/Night
For 7 Nights CA $4,370
1 Bedroom
1 Bathroom
Couples Retreat
Bed & Breakfast
- Hot Tub
- Pool
- Balcony/Terrace
CA $462/Night
For 7 Nights CA $3,237
1500 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $451/Night
For 7 Nights CA $3,155
1905.21 ft²
10 Guests
10 Bedrooms
2 Bathrooms
Family Friendly
House
- Skiing
- Fireplace/Heating
- Pool
CA $898/Night
For 7 Nights CA $6,289
1000 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $279/Night
For 7 Nights CA $1,956
1100 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $413/Night
For 7 Nights CA $2,889
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $279/Night
For 7 Nights CA $1,956
Lee Luxury Rentals
10 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
CA $2,048/Night
For 7 Nights CA $14,336
2800 ft²
14 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $1,292/Night
For 7 Nights CA $9,041
2393 ft²
15 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- Balcony/Terrace
CA $1,192/Night
For 7 Nights CA $8,345
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
CA $1,175/Night
For 7 Nights CA $8,224
2300 ft²
10 Guests
5 Bedrooms
10 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
CA $844/Night
For 7 Nights CA $5,907
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $815/Night
For 7 Nights CA $5,705
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $807/Night
For 7 Nights CA $5,647
3000 ft²
9 Guests
5 Bedrooms
3 Bathrooms
Ocean View
Other
- Private Pool
- Fireplace/Heating
- Pool
CA $795/Night
For 7 Nights CA $5,566
Lee Pet Friendly Vacation Rentals
600 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $197/Night
For 7 Nights CA $1,376
2034.38 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Parking
CA $695/Night
For 7 Nights CA $4,865
4 Guests
2 Bedrooms
2 Bathrooms
Couples Retreat
Apartment
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
CA $477/Night
For 7 Nights CA $3,342
204.51 ft²
16 Guests
28 Bedrooms
3 Bathrooms
Cabin
- Skiing
- Fireplace/Heating
- Pet Friendly
CA $241/Night
For 7 Nights CA $1,686
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $771/Night
For 7 Nights CA $5,395
1600 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $499/Night
For 7 Nights CA $3,495
9 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
CA $516/Night
For 7 Nights CA $3,612
2037 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $662/Night
For 7 Nights CA $4,632
Lee Large Vacation Homes
2800 ft²
11 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $660/Night
For 7 Nights CA $4,620
306.77 ft²
15 Guests
10 Bedrooms
6 Bathrooms
Bed & Breakfast
- Spa
- Skiing
- Fireplace/Heating
CA $508/Night
For 7 Nights CA $3,554
3500 ft²
20 Guests
5 Bedrooms
6 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- Balcony/Terrace
CA $1,730/Night
For 7 Nights CA $12,112
211.69 ft²
34 Guests
11 Bedrooms
11 Bathrooms
Ocean View
Bed & Breakfast
- Oceanfront
- Skiing
- Fireplace/Heating
CA $506/Night
For 7 Nights CA $3,544
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Spa
- Fireplace/Heating
CA $725/Night
For 7 Nights CA $5,078
11 Guests
4 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
CA $815/Night
For 7 Nights CA $5,705
24 Guests
9 Bedrooms
10 Bathrooms
Group Friendly
Bed & Breakfast
- Fireplace/Heating
- Air Conditioner
- Internet
CA $8,814/Night
For 7 Nights CA $61,698
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Internet
CA $618/Night
For 7 Nights CA $4,326
Why Choose Rent By Owner for your Lee Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Lee
When should you plan your Vacation Rentals stay?
Timing your visit to this charming area ensures you experience its best weather and local events, making your stay in Lee, Massachusetts the most enjoyable when you choose the ideal time for your vacation.
Peak Season Highlights
Summer (June to August)
During the summer months, the region experiences warm weather ideal for outdoor activities and exploring. This is the most popular time to visit, so booking your vacation rental early ensures you secure the best options and rates.
Average Temperature Daytime: around 75°F to 85°F - Nighttime: about 55°F to 65°F
Fall (September to November)
Autumn brings colorful foliage and mild temperatures, making it a scenic time to enjoy the area's natural beauty. It’s a busy season for vacation rentals, so planning ahead guarantees access to prime properties.
Average Temperature Daytime: roughly 65°F to 75°F - Nighttime: around 45°F to 55°F
Off-Season Highlights
Winter (December to February)
In winter, the region's peaceful atmosphere offers a serene retreat with fewer crowds. This season is perfect for cozy stays in well-appointed vacation rentals, often at more affordable rates.
Average Temperature Daytime: approximately 30°F to 40°F - Nighttime: near 15°F to 25°F
Spring (March to May)
Springtime welcomes milder weather and blooming landscapes, creating a refreshing setting for your stay. With fewer visitors, it’s an excellent opportunity to enjoy flexible booking options and more personalized experiences.
Average Temperature Daytime: around 50°F to 60°F - Nighttime: about 35°F to 45°F
Weekly Weather Forecast for Lee
How to Book Your Lee Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Lee
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or deck to relax and entertain in the fresh air.
- Take advantage of well-maintained gardens or landscaped yards that enhance your outdoor experience.
- Make use of a grilling area or outdoor kitchen for family cookouts and gatherings.
- Benefit from access to shared or private swimming pools during the warmer months.
- Experience outdoor dining spaces perfect for enjoying meals with scenic views.
- Utilize nearby walking trails, hiking paths, or nature preserves right from your rental property.
- Relax by an outdoor fire pit, ideal for evenings spent with friends or family under the stars.
Top Attractions Around Lee
What attractions are nearby?
Within the area, you can enjoy a variety of outdoor activities and cultural experiences that highlight the charm of this destination, making your stay memorable and engaging.
Family Activities
- Lee Family Fun Center: Enjoy a family-friendly day at this local amusement center, offering activities that keep kids entertained and engaged.
- Tanglewood Music Center: Experience outdoor concerts and performances in a lush, scenic setting perfect for family outings during the warmer months.
- The Williams River Preserve: Explore nature trails and wildlife viewing opportunities along the river, ideal for adventurous families seeking outdoor recreation.
- The Village Green: Spend quality time together at this charming town square, hosting seasonal events, markets, and community gatherings suitable for all ages.
Adult Activities
- Lee Premium Outlets: Enjoy a leisurely shopping experience at this popular outlet mall, offering a variety of brand-name stores just a short drive from your accommodations.
- Norman Rockwell Museum of Western Massachusetts: Explore the works and legacy of Norman Rockwell, with exhibits that celebrate American art right in the heart of the region.
- Lee Farmers’ Market: Visit the local farmers’ market to sample fresh produce, baked goods, and artisan crafts, perfect for immersing yourself in the area's vibrant community spirit.
- Monument Mountain Regional High School Performing Arts Center: Attend captivating performances and cultural events hosted at this regional hub, providing entertainment and cultural enrichment during your stay.
Other Places to Stay in Lee, MA
Tyringham
Wood's Pond
Berkshire Scenic Railway Museum
Greenock Country Club
Lee Library
Animagic Museum of Animation
Berkshire Mountain Country Store
Lee Prime Outlets
Ashintully Gardens
Tyringham Cobble
McLennan Reservation
Goose Pond Reservation
Lee Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities Ahead: Explore local outdoor trails and cultural sites in the area to make the most of your stay and enjoy the region’s natural beauty.
- Choose a Prime Location: Select a vacation rental close to key attractions or scenic spots in Lee to maximize your experience and minimize travel time.
- Embrace Seasonal Events: Check for seasonal festivals or community events in the region that can enrich your visit and offer authentic local experiences.
- Prioritize Comfort & Convenience: Look for well-equipped vacation rentals with amenities that suit your needs, ensuring a relaxing and enjoyable retreat in this destination.
Transportation Options
- Massachusetts Bay Transportation Authority (MBTA) Service: You can access regional rail and bus services that connect here to major cities and neighboring towns, making it convenient to explore the area without a car.
- Private Shuttle Services: Several private shuttle providers operate in this part of Massachusetts, offering direct transportation to nearby airports and popular destinations within the region.
- Rental Car Agencies: National and local rental car companies are available nearby, giving you the flexibility to explore this destination and its surroundings at your own pace.
- Local Taxi and Ride-Sharing: Taxis and ride-sharing options like Uber and Lyft are readily accessible, providing easy and quick transport within the region for day trips or short outings.
Local Customs Options
- Traditional New England Hospitality: Locals in Lee embrace a welcoming attitude rooted in the region's historic New England customs, making you feel at home from your arrival.
- Harvest Festivals: Celebrating the region's agricultural heritage, annual harvest festivals featuring local produce and crafts are cherished community events that visitors often enjoy participating in.
- Respect for Nature: The area's commitment to preserving natural beauty is reflected in outdoor etiquette and conservation efforts, encouraging respectful exploration of the scenic surroundings.
- Regional Culinary Traditions: Savoring locally inspired dishes and seasonal flavors is a common custom here, adding an authentic taste of the region to your stay.
Frequently Asked Questions About Lee?
1. What are the top vacation rentals in Lee?
There are a lot of options in Lee. If you plan on staying in the Lee area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Lee:
- Devonfield Inn B&B
- Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
- Elegant 19th Century New England 2BR vacation rental at Garfield House
- Spectacular setting on your own private lake close to it all!
- The Freckled Hen's Berkshire Nest
- Modern And Spacious Berkshires Retreat 5 bdrm 3 bath
- 1500 sqft private entrance with beautiful views of the Berkshire Mountains
- Ashintully Cottage in spectacular setting
- 2 Bedroom renovated townehouse, #5 , Beautifully decorated at Garfield House
- Lovely Lakefront Cottage, Peaceful Setting, Hiking And More
2. How many vacation rentals have private pools in Lee?
There are 1 vacation rentals with private pools near Lee. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Lee are best for families?
If you are looking for a family-friendly vacation home in Lee, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Lee:
4. How many Rentbyowner vacation rentals are available in Lee?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 96 in the Lee area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Lee.
5. What is the cancellation policy for vacation rentals in Lee, Massachusetts?
Cancellation policies vary for each property listed here. To understand the specific terms and any potential fees, please review the details outlined on the individual listing or contact the owner directly before booking.
6. How do I know if a vacation rental in Lee, Massachusetts is available for my travel dates?
Availability is typically updated in real-time on the listing page. If your desired dates are not visible as available, you can reach out to the property owner for confirmation or inquire about flexible booking options.
7. Are there any additional fees I should be aware of when booking a vacation rental in this destination?
Additional fees such as cleaning charges, service fees, or security deposits may apply. For precise information, please check the breakdown provided in the listing details or contact the owner for clarification.
8. What amenities can I expect from vacation rentals in the region?
Amenities vary by property but often include essentials like Wi-Fi, parking, and kitchen facilities. To ensure the rental meets your needs, review the amenities listed on each property’s page or contact the owner directly.
9. What should I know about checking in and out at vacation rentals in Lee, Massachusetts?
Check-in and check-out procedures are specified in each listing. Be sure to read these details carefully or communicate with the owner to confirm your arrival time and departure requirements for a smooth stay.
Lee Top Rated Vacation Rentals
9 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
CA $359/Night
For 7 Nights CA $2,517
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $530/Night
For 7 Nights CA $3,711
CA $155/Night
For 7 Nights CA $1,083
CA $125/Night
For 7 Nights CA $872
2551.05 ft²
12 Guests
5 Bedrooms
2 Bathrooms
House
- Pool
- Balcony/Terrace
- View
CA $630/Night
For 7 Nights CA $4,409
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Spa
- Fireplace/Heating
CA $479/Night
For 7 Nights CA $3,356
2497 ft²
9 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Spa
- Fireplace/Heating
CA $533/Night
For 7 Nights CA $3,734
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Air Conditioner
CA $184/Night
For 7 Nights CA $1,287
