Search Condo Rentals in Lenox

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 38 Condo Rentals in Lenox with updated reviews, rates, and availability.

Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
Exterior
Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
10.0 out of 10, Exceptional, (6)
"The property was as advertised. Clean and comfortable. And right on the mountain - ski-in/ski-out. Perfect for families."
Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.
Exterior
Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.
9.8 out of 10, Exceptional, (9)
"The unit was clean and was accurately described on the listing. Check in was easy. This was our second time here and will return again."
Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Interior
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
9.4 out of 10, Exceptional, (12)
"Justine was a great host, and was quick to respond to all my texts. The condo was clean equipped with the basic amenities. He provided us with a drip coffee machine, but you could also get complimentary Keurig coffee every morning from the lobby. The only small inconvenience to our stay was that there was no heat in the living room, and although there is a vent from the bedroom into the living room, it didn't seem to circulate the warm air from the bedroom into the living room. The front desk...
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Exterior
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
10.0 out of 10, Exceptional, (5)
"We love Bentley Brook! We will come back next year!"
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Snow and ski sports
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
10.0 out of 10, Exceptional, (21)
"I cannot say enough good things about this condo and the host! Colin was so easily reachable and even last minute we were able to add another night onto our stay. We had 2 little ones and 4 adults and we were so comfortable with all the space. Every amenity you think you may need was there, we didn’t find ourselves saying “Oh I wish there was…” one time! It was the perfect location for us while our group was there meeting in that building. The balcony views were phenomenal and if our group comes...
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Snow and ski sports
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
10.0 out of 10, Exceptional, (33)
"We loved our stay at this beautiful condo. Clean and perfectly suited at the base of Jiminy Peak. Host was responsive and provided excellent detailed instructions."
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
UNIQUE - 1BR Country Condo @ Jiminy Peak
Room
UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (8)
"Very comfortable and convenient space. It easily accommodated me and my two teenaged children. The proximity to the ski lifts at Jiminy Peak is a great feature."
UNIQUE - 1BR Country Condo @ Jiminy Peak
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Exterior
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.
Room
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.
4.0 out of 10, (1)
"Listing is inaccurate. Clearly said 2 bedrooms in ad., but it is only 1."
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Snow and ski sports
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
9.6 out of 10, Exceptional, (7)
"Everything was perfect for a ski weekend"
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Property grounds
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
9.6 out of 10, Exceptional, (5)
"Perfect stay at Jiminy Peak. Unit had everything I needed."
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Ski In & Ski Out - Deluxe 1 Bedroom Condo
Exterior
Ski In & Ski Out - Deluxe 1 Bedroom Condo
10.0 out of 10, Exceptional, (6)
"We love Jiminy Peak and having a week at a ski-in, ski-out unit was fantastic. We skied back for lunch and skied back out for the afternoon; skied in for a quick dinner and the boys skied back out for night skiing. Terrific location! Kitchen was clean and serviceable (no oven but two burners, sink, dishwasher, microwave, and toaster) and beds were good. Everything was easy... check in, check out, so smooth. A great time was had by all!!!!"
Ski In & Ski Out - Deluxe 1 Bedroom Condo
Outside Adventure-Skiing, Hiking, and Relaxation
Snow and ski sports
Outside Adventure-Skiing, Hiking, and Relaxation
10.0 out of 10, Exceptional, (1)
"Weather didn't help but the rental and the location were exceptional!"
Outside Adventure-Skiing, Hiking, and Relaxation
Ski on ski off 1 Br loft condo in the village center with private gated parking
Property grounds
Ski on ski off 1 Br loft condo in the village center with private gated parking
10.0 out of 10, Exceptional, (13)
"My friends and I were looking for a close escape from Albany, NY. When we entered the condo we immediately felt a sense of ease and once the wood burning fire was started we were in heaven. The condo is in the perfect location within the JP Village. We were able to walk to the Country Store, Bars and Restaurants. What was PERFECT was the close proximity to the lifts; right out the door. We could ski on, ski off and take breaks without dealing with the crowds in the food halls. The condo itself...
Ski on ski off 1 Br loft condo in the village center with private gated parking
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Exterior
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
10.0 out of 10, Exceptional, (1)
"We very much enjoyed our stay. The place was very comfortable and very clean. The location worked out perfect and the parking was very convenient."
Mountainside Wyndham Bentley Brook! 2 Bd. dlx.
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock
Exterior
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock
10.0 out of 10, Exceptional, (1)
"great stay as always!"
Wyndham Bentley Brook! 2 Bd. dlx. in Hancock
Ski Jiminy Peak Xmas wk Thurs-Sun 3 nites; Ski In/Ski Out @Wyndham Bentley Brook
Exterior
Ski Jiminy Peak Xmas wk Thurs-Sun 3 nites; Ski In/Ski Out @Wyndham Bentley Brook
Ski Jiminy Peak Xmas wk Thurs-Sun 3 nites; Ski In/Ski Out @Wyndham Bentley Brook
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Exterior
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
10.0 out of 10, Exceptional, (9)
"Love the ski in and out of this property. Family enjoyed staying here, highly recommended."
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Perfect for Winter Skiing!!
Exterior
Perfect for Winter Skiing!!
Perfect for Winter Skiing!!
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Snow and ski sports
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Don't see what you're looking for?
See all available 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.

Other property types in Lenox

Fox Hollow Luxury Ranch Laurel Lake
Property grounds
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
The Kemble- Built by a US Secretary of State in Lenox
The Kemble - a registered Great Estate
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (15)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
The Winthrop Estate - 12K SF 32 Acres
The Winthrop
The Winthrop Estate - 12K SF 32 Acres
10.0 out of 10, Exceptional, (2)
"Absolutely stunning property - truly incredible stay. Recommend to anyone looking for a large group getaway. Fast WiFi, commercial grade kitchen and plentiful supplies make it easy for large groups. beautiful property and room for activities on a huge lawn. Highly recommend."
The price is SAR 11,196
SAR 17,915 total
includes taxes & fees
13 Jum. II - 14 Jum. II
The Winthrop Estate - 12K SF 32 Acres
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.

Recent reviews of Lenox hotels
Expedia verified reviews

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

5/5 Excellent
Beautiful Berkshires
"Very accommodating. No frills. Good enough for a few nights. "
A verified traveler stayed at Howard Johnson by Wyndham Lenox
Posted 1 day ago
Howard Johnson by Wyndham Lenox