Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
20 min drive
Room options
About the neighborhood
Stockbridge
On lake.Stay at this Stockbridge vacation home and you'll be within half a mile (1 km) of Stockbridge Bowl and 2 miles (3 km) of Frelinghuysen Morris House and Studio. Tanglewood Music Center and The Mount are also within 3 miles (5 km).
Ventfort Hall Mansion and Gilded Age Museum - 7 min drive - 2.9 miles
Norman Rockwell Museum - 8 min drive - 4.2 miles
National Shrine of the Divine Mercy - 10 min drive - 3.8 miles
Getting around
Pittsfield Intermodal Transportation Center - 22 min drive
Pittsfield, MA (PSF-Pittsfield Municipal) - 21 min drive
Restaurants
1894 Fireside Bistro & Bar - 9 min drive
Haven Cafe & Bakery - 6 min drive
Bernstein Shack - Tanglewood - 7 min drive
Harvest Moon - 9 min drive
Olde Heritage Tavern - 6 min drive
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Grandma's Cottage on The Bowl
Welcome to our rustic summer cottage—quaint, quirky, and perfectly imperfect! Nestled right at the Stockbridge Bowl in the Berkshires, it’s the spot for water lovers and Tanglewood fans alike. With more charm than shiny new, this cozy retreat is ideal for those who appreciate rustic charm and a splash of personality. Just 3 minutes from Tanglewood, it’s a step back in time where moments with family abound and good times float freely!
– Beautiful lake views from the cottage to enjoy morning to night.
– Right on the Stockbridge Bowl ideal for swimming, boating, or enjoying Tanglewood nearby.
– Modern comforts included: free Wi-Fi, air conditioning, full kitchen, washer/dryer, and pet- and kid-friendly setup.
Location & Views Imagine waking up and stepping onto the deck, where you’re greeted by sweeping vistas of Stockbridge Bowl. This outdoor space is ideal for breakfast, lunch, or dinner with friends and family while gazing out over the shimmering water. It’s the perfect spot to soak in the peaceful surroundings of the berkshire hills.
Living Space & Bedrooms The house, though on the older side, is still quite comfy. It features a spacious open living room and a generous dining area—great for cozy nights in. With three bedrooms and 2.5 baths, there are five beds ready to host your group. We prefer keeping it to a maximum of six guests to maintain a mellow neighborhood vibe, but there’s plenty of room for everyone to relax and enjoy.
Kitchen & Amenities A simple, functional kitchen equipped with the basics—perfect for whipping up home-cooked meals or snacks after a day on the water. While it doesn’t boast modern upgrades, it’s fully set up to help you create delicious memories.
Setup & Outdoor Fun The home spans two levels, so guests will need to be comfortable with stairs. Outside, you’ll find a few sun loungers ready for basking in the sun, plus a straightforward propane grill for backyard barbecues. Whether you’re relaxing by the water, grilling with friends, or just enjoying the serene lake views, this spot has everything you need for an enjoyable stay.
***IMPORTANT NOTE, WE ARE NOT ALLOWED TO HAVE TRASH CANS AT THE COTTAGE. ALL GUESTS WILL NEED TO BRING THEIR TRASH TO THE TOWN DUMP, JUST A FEW MINUTES DOWN THE ROAD. ***IMPORTANT NOTE, PER HOA REGULATIONS WE ARE NOT ALLOWED TO KEEP ANY TRASH BINS OUTSIDE AT THE PROPERTY. ALL GUESTS WILL BE REQUIRED TO BRING TRASH TO THE LOCAL TRANSFER STATION, JUST A SHORT DRIVE DOWN THE ROAD.
To make your stay at Mahkeenac Shores more pleasant and safe for both you and your summer neighbors here, we respectfully ask that your group observe the following:
• Please observe all stop signs and the 10 mph speed limit at all times. All drivers should be extremely careful of children and others and be mindful that Mahkeenac Shores Road is one-way.
• All persons must be quiet after 9 p.m. This is a Town ordinance.
• No child under 10 years of age may fish unless supervised by an adult. All fishing should be done from the end of the wood dock that is perpendicular to the shoreline, or from a boat; no fishing should be done from the wood dock that is parallel to the shoreline.
• Members and their guests are expected to carry away all their own litter, trash and personal belongings, including toys and gear, from the community lot and dock when they leave for the day.
• Our umbrellas at the community dock can be a delight and relief. Please help us extend their lives by closing them before you leave our dock.
• No person may use any boat unless he/she has the permission of the owner.
• If you plan to use a boat that has been in another body of water in the past week, you must first clean it with soap and water; or bring it to be washed at the Inspection and Washing Station on Route 183, just south of Kripalu. This measure is a must, to prevent the invasion of Zebra Mussels that can destroy our lake.
• No person may play with either a baseball or a softball in the community lot, unless the ball is soft or lightweight (think wiffle ball!).
Similar properties
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
First aid kit
Fire extinguisher
Policies
Check-in
Check-in time starts at 3:00 PM
Minimum check-in age: 25
Check-out
Check-out before 11:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Pets
Pets are welcome
Service animals are exempt from fees
Children and extra beds
Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.
Property is also known as
396469
Frequently asked questions
How close is Grandma's Cottage on The Bowl to the airport?
This vacation home is 8.8 mi (21-min drive) away from the Pittsfield, MA (PSF-Pittsfield Municipal) airport, the closest popular airport to the property.
Does Grandma's Cottage on The Bowl have an airport shuttle?
Airport shuttle services are not available at this vacation home.
Does Grandma's Cottage on The Bowl offer free breakfast?
This vacation home does not offer free breakfast.
Is there a casino at Grandma's Cottage on The Bowl?
No, there is no casino at this vacation home.
What time is check-in at Grandma's Cottage on The Bowl?
Check-in begins at 3:00 PM.
Is there free parking at Grandma's Cottage on The Bowl?
Free parking is not available at this vacation home.
Does Grandma's Cottage on The Bowl have a pool?
This vacation home does not have a pool.
Does Grandma's Cottage on The Bowl have a spa?
There are no spa services available at this vacation home.
How close is Grandma's Cottage on The Bowl to downtown Stockbridge?
This vacation home is 3 mi away from Stockbridge.
Reviews
Grandma's Cottage on The Bowl Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
8.0/10
Cleanliness
Rating 10 - Excellent. 1 out of 1 reviews
10 - Excellent
1
Rating 8 - Good. 0 out of 1 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 1 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 1 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 1 reviews
2 - Terrible
0
Reviews
10/10 Excellent
Julie H.
Oct 13, 2025
Liked: Cleanliness
A lovely cabin in a cozy neighborhood. Had everything we needed for a long weekend. Host is very responsive.