Lenox Vacation Packages

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Your Lenox Vacation

There's loads to like about Lenox, from its cultural experiences to its spectacular views. When you're ready to say hi to this interesting city, our Lenox vacation packages are calling your name. Make your trip to Lenox even more fun by going sightseeing. Tanglewood Music Center, National Shrine of the Divine Mercy and Lee Premium Outlets are some of the major attractions you'll want to explore. No matter your travel plans or budget, organizing a tailored Lenox vacation is a walk in the park with Expedia.

Top Lenox Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was CA $1,441, price is now CA $1,107 per person
CA $1,107
per person
Sep 26 - Oct 1
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
9.4/10 Exceptional! (153 reviews)
Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was CA $2,197, price is now CA $1,276 per person
CA $1,276
per person
Sep 26 - Oct 1
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
9/10 Wonderful! (2 reviews)
Prospect was a wonderful stay with very friendly staff. The property is very well maintained. We had a great time with the all the lake activities. Would definitely recommend for a quick getaway

Reviewed on Jun. 23, 2025

Hasbrouck House

Hasbrouck House

4 out of 5
Price was CA $2,679, price is now CA $1,938 per person
CA $1,938
per person
Sep 26 - Oct 1
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
9.2/10 Wonderful! (46 reviews)
Great getaway property. We checked in for two nights, and stayed in a building with kitchen/2 bedrooms, which was great for our needs. We spent time in the property relaxing at the beautiful pool, sauna, and had a fabulous dinner at Butterfield. Played some shuffleboard, pool and video games in their clubhouse - very laid back vibe and perfect for a couples weekend. Great food options off property in the area, and my partner was able to get in a quick nine-hole game of golf at a nearby course.

Reviewed on Aug. 6, 2025

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

3 out of 5
Price was CA $1,877, price is now CA $1,490 per person
CA $1,490
per person
Sep 26 - Oct 1
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
No reviews
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3 out of 5
Price was CA $3,561, price is now CA $2,995 per person
CA $2,995
per person
Oct 2 - Oct 6
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
No reviews

Ready to book your vacation to Lenox?

 

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Lenox Hotel Deals

Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from Aug 26 to Aug 27
CA $222
CA $248 total
Aug 26 - Aug 27
includes taxes & fees
9/10 Wonderful! (687 reviews)
"We loved everything! Josh was great at check in and with recommendations. Nick was truly fabulous bartending and giving us helpful suggestions and tips. Aurora was extremely helpful as well. 5 stat hotel in a great location with an awesome bar and restaurant. Hamburgers were off the chart. Thank ..."

Reviewed on Aug. 18, 2025

Berkshires Untold
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Sep 1 to Sep 2
CA $110
CA $123 total
Sep 1 - Sep 2
includes taxes & fees
7.6/10 Good! (785 reviews)
"The room was enormous didn't feel cramped at all like some hotels. There for one night, the pool looked pretty decent, didn't have time to try it out. The room had a fairly strong odor of old cigarette smoke. A deep cleaning would probably help. The carpet seemed fairly new, but felt as though it ..."

Reviewed on Aug. 17, 2025

Howard Johnson by Wyndham Lenox
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Sep 1 to Sep 2
CA $169
CA $189 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"My stay was very good"

Reviewed on Aug. 19, 2025

The Yankee, Trademark Collection by Wyndham
See all 1,420 properties in Lenox
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.
All Inclusive Vacations
All Inclusive Vacations
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Discover the most popular places to visit in Lenox

Ventfort Hall Mansion and Gilded Age Museum

You can spend an afternoon exploring the galleries in Ventfort Hall Mansion and Gilded Age Museum during your travels in Lenox. Wander the lakeside in this family-friendly area.

Ventfort Hall Mansion and Gilded Age Museum

Lenox Library

Lenox Library is just one of the places to see in Lenox, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's gardens or attend a sporting event.

Lenox Library

Frequently asked questions

How much does a Lenox vacation package cost?
You'll find cheap prices from CA $1,107 on Expedia for your Lenox getaway. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Lenox costs.
What are the cheapest months to go to Lenox?
If you'd like to snag a cheap Lenox vacation package, consider travelling in January, March and April. You'll generally find better rates on hotels and airfares during these quieter months — ideal for a budget-friendly break.
How many days is enough for Lenox?
You can visit all the major attractions in Lenox in a few days, including the must-see The Mount. If you're looking for a longer Lenox vacation, look at what kind of excursions and activities are available close by.
Is it worth booking a vacation package to Lenox?
It's no wonder a Lenox vacation is on the must-do list of many travellers. Leading attractions like The Mount are just the beginning of things to see and do here.
How to find the best Lenox package deals?
Finding a cheap Lenox package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Lenox package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Lenox vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component separately. And you'll still get the freedom to create a tailored Lenox vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Lenox?
If you've got your Lenox travel dates finalized, book early to bag some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Lenox?

  1. Choose when to travel: Check your diary and pack your bags. Your preferred season and the type of activities on offer will also help you decide when to vacation in Lenox.
  2. Plan your budget wisely: In addition to the cost of your hotel, you'll need to consider other expenses too. These include food, transportation and flights. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Lenox.
  3. Decide how many days away: Start by compiling a list of the activities and sights you want to experience in Lenox. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a tailored Lenox vacation package.

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