Lee Vacations from $523

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Your Lee Vacation

With one of our vacation packages to Lee, you'll have countless opportunities for relaxation and adventure. There's plenty to enjoy, including its rural countryside and spectacular views. A trip to Lee is an excellent opportunity to do a bit of sightseeing. Make sure you visit renowned attractions like Tanglewood Music Center, National Shrine of the Divine Mercy and Lee Premium Outlets. Expedia is here to help you escape the everyday. Tailor your vacation to Lee to suit your style of travel, whatever that may be.

The Latest Lee vacation packages

Price found within the past 48 hours. Click for updated prices.
Gedney Farm

Gedney Farm

3.5 out of 5
Save 100% on your flight
Price was $759, price is now $523 per person
$523
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.4/10 Exceptional! (132 reviews)
My wife and I chose Gedney Farms at the last minute to enjoy a quick escape from the city. The staff was friendly and welcoming. The checkin and checkout experience was seamless. The room had a truly rustic charm, and clean and orderly. In the morning we took a nice walk on the grounds. For a quick and relaxing getaway, Gedney Farms is a great choice.

Reviewed on Nov 2, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,723, price is now $1,026 per person
$1,026
per person
Dec 28 - Jan 2
found 23 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.8/10 Exceptional! (13 reviews)
Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay....

Reviewed on Oct 20, 2025

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
Save 100% on your flight
Price was $1,303, price is now $824 per person
$824
per person
Dec 28 - Jan 2
found 23 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.4/10 Exceptional! (110 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Save 100% on your flight
Price was $1,141, price is now $769 per person
$769
per person
Dec 28 - Jan 2
found 23 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
17.6/10 Exceptional! (3 reviews)
The room was nice and clean, but the hotel itself was still under construction and it took 45 minutes for us to get in our room for check-in I was able to ask for extended check out and we got two complementary drinks from the bar but overall they should have waited to open

Reviewed on Nov 12, 2025

Church Des Artistes Guest House

Church Des Artistes Guest House

3 out of 5
Roundout
Save 100% on your flight
Price was $5,233, price is now $3,586 per person
$3,586
per person
Dec 28 - Jan 2
found 23 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.8/10 Exceptional! (18 reviews)
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Discover the most popular places to visit in Lee

Lee Premium Outlets

You can find the perfect gifts to bring home at Lee Premium Outlets during your trip to Lee. Amble around the area's gardens or attend a sporting event.

Lee Premium Outlets

Berkshire Mountain Country Store

You can enjoy the entertainment at Berkshire Mountain Country Store during your travels to Lee. Wander the gardens and forest in the area.

Berkshire Mountain Country Store

Goose Pond Reservation

Commune with nature and explore the great outdoors at Goose Pond Reservation during your travels in Lee. While you're here, you can savor the top-notch restaurants.

Goose Pond Reservation

Lee Hotel Deals

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
Fully refundable
$106 nightly
The price is $119 total per night from Dec 11 to Dec 12
$119 total
Dec 11 - Dec 12
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
The room was nice, but wish we would have asked for the lake view. The breakfast area was really nice and they had good food. The coffee machine was available 24/7 and it made a pretty good mocha!

Reviewed on Nov 12, 2025

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street Lee MA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Dec 7 to Dec 8
$104 total
Dec 7 - Dec 8
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Clean spacious room. Friendly staff at check in. Breakfast room was small but not difficult to get a table. Good location with restaurants within walking distance.

Reviewed on Nov 9, 2025

Quality Inn
Chambery Inn

Chambery Inn

3 out of 5
199 Main St Lee MA
$190 nightly
The price is $212 total per night from Nov 23 to Nov 24
$212 total
Nov 23 - Nov 24
Total with taxes and fees
9.4/10 Exceptional! (372 reviews)
We LOVED our mini getaway at the Chambery Inn. The room was gorgeous, spacious, and very comfortable. The fireplace couldn't have been easier to operate. The jetted tubs were divine with plenty of hot water the towel warmer was a nice bonus. The room was fully stocked with glassware and a corkscrew ...

Reviewed on Nov 3, 2025

Chambery Inn
See all 497 properties in Lee
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Lee Vacation Packages

Lee Essential Information

Language
English
Currency
U.S dollars
Population
2,100
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Norman Rockwell Museum, Ski Butternut and Bousquet Ski Area

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Frequently asked questions

How much does a Lee vacation package cost?
You'll find cheap prices from $523 on Expedia for your Lee escape. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Lee costs.
What are the cheapest months to go to Lee?
You can typically find lower prices and greater availability in November, December and January. Check out our cheap Lee vacation packages and you could score some great off-season discounts.
How many days is enough for Lee?
Usually, a handful of days is enough to go to the main attractions during your Lee vacation. But if you'd like to have time to chill out or take day tours, think about extending your itinerary.
Is it worth booking a vacation package to Lee?
Lee is a good vacation destination with attractions like Lee Premium Outlets among the many things to keep you entertained. Whether you're heading away with the family or planning a trip with friends, a Lee vacation promises a good time for everyone.
How to find the best Lee package deals?
Start your search for a Lee package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Lee package deal right away, simply play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Lee escape off to a flying start.
Is it cheaper to book a Lee vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking accommodations and flights individually. Better still, you can personalize your Lee escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Lee?
Land fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Lee break.
Does Expedia offer Book Now, Pay Later Lee vacation packages?
Your Lee break is meant to be a relaxing escape from your busy life, not a source of money worries. So to give you that extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.