Lenox Mountain Tours and Activities

Plan a trip to see Lenox Mountain

Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Price was CA $773, price is now CA $598 per person
CA $598
per person
Apr 28 - May 1
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,111 reviews)
Clean room and great staff

Reviewed on Feb 16, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,272, price is now CA $1,955 per person
CA $1,955
per person
Apr 28 - May 1
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

The Preserve Sporting Club & Resort

The Preserve Sporting Club & Resort

4 out of 5
Price was CA $5,000, price is now CA $3,496 per person
CA $3,496
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Providence (PVD)
8.8/10 Excellent! (8 reviews)
The resort itself stood out so beautiful!

Reviewed on Jan 6, 2026

Popular places to visit

Bye fall

Pleasant Valley Wilderness Sanctuary

Explore the great outdoors at Pleasant Valley Wilderness Sanctuary, a lovely green space in Lenox. Wander the lakeside in this quaint area.

Pleasant Valley Wilderness Sanctuary
Hardly anyone here! Great way to spend a week day, skiing and tubing!

Bousquet Ski Area

Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this family-friendly area.

Bousquet Ski Area
Hancock Shaker Village, Hancock Massachusetts beautiful place; description Shakers, all supported themselves by the proceeds of their farmland. The Hancock Shakers were primarily dairy farmers. The raising and sale of garden seeds was perhaps the most lucrative of their early businesses.Land acquisition and conversion continued for decades, with the area peaking at 3,000 acres

Hancock Shaker Village

4.5/5(3 reviews)

You can browse the exhibits at Hancock Shaker Village, a museum with a storied past, during your trip to Pittsfield. Wander the lakeside in this quaint area.

Hancock Shaker Village
A road near Tanglewood. Driving through the Berkshires is never a disappointing #roadtrip

Tanglewood Music Center

5/5(6 reviews)

You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.

Tanglewood Music Center

Lenox Mountain Reserve

You can take time to visit Lenox Mountain Reserve during your travels to Richmond. Discover the mountain views while you're in the area.

Lenox Mountain Reserve

Nordeen Marsh Natural Heritage Area

You can take time to visit Nordeen Marsh Natural Heritage Area during your travels to Richmond. Discover the mountain views while you're in the area.

Nordeen Marsh Natural Heritage Area

Best Lodging Options Near Lenox Mountain

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Berkshire Mountain Lodge
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
The Yankee, Trademark Collection by Wyndham
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Berkshires Untold
Country Living just minutes from Everything!

Country Living just minutes from Everything!

Pittsfield MA
Country Living just minutes from Everything!
Escape to The Berkshires w/Pool by Evergreen Home

Escape to The Berkshires w/Pool by Evergreen Home

Richmond MA
Escape to The Berkshires w/Pool by Evergreen Home
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
Hampton Inn & Suites Berkshires-Lenox
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St Pittsfield MA
Best Western Plus Berkshire Hills Inn & Suites
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd Lenox MA
Courtyard by Marriott Lenox Berkshires
Element Lenox Berkshires

Element Lenox Berkshires

3 out of 5
130 PITTSFIELD ROAD Lenox MA
Element Lenox Berkshires
See all 735 properties in Lenox Mountain
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now