Cummington Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Browse Select Cummington Vacation Homes

Our top choices for Cummington vacation homes

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (5)
Contemporary Berkshire Home with Views of Taconic Golf Course

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (70)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is CA $223
CA $670 total
includes taxes & fees
Aug 27 - Aug 28
Comfortable Berkshires retreat on mtn resort, SISO

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

9.6 out of 10, Exceptional, (8)
"The house was clean, nicely decorated, comfortable and all the amenities we needed! "
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (37)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (32)
"Easy stay, good location for us. Would stay again. "
The price is CA $161
CA $278 total
includes taxes & fees
Aug 27 - Aug 28
Lovely 2nd Floor Apartment

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

9.8 out of 10, Exceptional, (107)
"My wife and I stayed in the upper apartment for 2 nights. The place was perfect in every aspect. It was clean, quiet and well equipped. Beds were comfortable and it was close the UMASS. We will definitely stay here again when we are in the area. "
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

10.0 out of 10, Exceptional, (20)
"This beautiful home was perfect for our short stay in Western Massachusetts. Everything was just lovely, clean, comfortable, quiet. Great hosts and so kind and accommodating to our needs. Thank you so much. We will definitely look to stay here again for future family visits. "
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (72)
"Was as nice as the pictures. A plus for a very comfortable king sized bed! Right in town for walking to shops and restaurants. Thank you!"
Heart of Lenox Walk to Town Cozy Cottage!

1840's Whaling Captain's Farm Estate, 6-10 guests

10.0 out of 10, Exceptional, (5)
"Such a beautiful home and property. We had a great time exploring during the day and spending time together at night. Sunsets over the pond are particularly lovely and the screened in porch and sitting around a fire in the chiminea outside are the perfect spots for a cocktail. We look forward to our next visit!"
1840's Whaling Captain's Farm Estate, 6-10 guests

StrautmanHaus - All-Season Chalet at Berkshire East

9.8 out of 10, Exceptional, (13)
"The house was definitely nice and we enjoyed our stay. I didn’t give it 5 stars because the two downstairs bedrooms had a strong musty smell."
StrautmanHaus - All-Season Chalet at Berkshire East

Historic Williams House 2-bedroom downtown Northampton with AC, WiFi

Historic Williams House 2-bedroom downtown Northampton with AC, WiFi

Walk to Dining: Downtown Lenox Guest House!

9.4 out of 10, Exceptional, (29)
"Great location and convenient walking distance to downtown Lenox. "
Walk to Dining: Downtown Lenox Guest House!

Charming 3-bedroom farmhouse in Lenox

10.0 out of 10, Exceptional, (1)
"House is comfortable and spacious, with a well-supplied kitchen. Hosts had thought of everything we might need. A/C was very helpful in the heat! Perfect location for exploring the Berkshires, and a fairly easy walk into town."
Charming 3-bedroom farmhouse in Lenox

Idyllic Berkshires Farmhouse

Idyllic Berkshires Farmhouse

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (28)
"Jandie's was the absolute best rental house we have ever stayed at. The house was clean and well kept, everything felt brand new. The set up was great, open kitchen, dining room and living room and made entertaining very easy. The kids had their own room and enjoyed spending time together in their own space. Julie was a pleasure to work with and accommodated us in anyway she could, from beginning to end. She even made us homemade delicious treats. We would highly recommend Jandie's and we...
Country Living just minutes from Everything!

Sophisticated Lenox Retreat by Evergreen Home

9.8 out of 10, Exceptional, (9)
"Very quaint location, clean property, and great place to stay"
Sophisticated Lenox Retreat by Evergreen Home

Spacious 5-bedroom house in charming Lee with WiFi

The price is CA $588
CA $1,103 total
includes taxes & fees
Sep 2 - Sep 3
Spacious 5-bedroom house in charming Lee with WiFi
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cummington Hotel Reviews