Classic Stockbridge Cottage | House in Stockbridge

10.0 (17 Reviews) |   Pet Friendly   4 Bedrooms  2 Bathrooms  8 Guests
Glendale House | Classic Stockbridge Cottage

4 Bedroom House in Glendale, Stockbridge

Summary:
Classic Southern Berkshire escape, built in the early 1900s by a cartographer for the NY Times. The home boasts a living room sized for entertaining, a separate library and an additional sitting space. The wood burning fireplaces in the living room and library bring warmth to enjoy your coffee on cold mornings. Light and bright kitchen adjoins the dining room with a screened-in porch for outdoor dining. Large decks on the front, side and back invite one outside at every turn.
The Space:
Upon arriving at the home you will see the lush landscaping and the Goshen stone steps that take you to the front door. You will notice the large deck
Enjoy a quiet moment in the living room with a crackling wood burning fireplace, antique spinet piano, comfortable sofa and four lounge chairs. This room also allows you to pick up the excitement by breaking out a board game in the nook with a game table and four chairs. If you’re looking to enjoy a good book or family movie, move over to the library where you will find a loveseat, two lounge chairs, wood burning fireplace and a Roku TV that you can log into your streaming apps such as Netflix, Hulu, amazon Prime, etc. At the end of your evening, relax and enjoy a drink in the lounge between the living room and kitchen. You will find a cozy loveseat, chair and classy bar cart. .
The dining area has lots of natural light with two sets of french doors leading to the outdoor wrap around deck. Easy access to the kitchen with the open peninsula to make setting up for large family meals easy. With the dining table with seating for eight and four seats at the peninsula, there is room for everyone!
The large open kitchen is recently updated and has some new appliances. The open spaces allow for you to be able to cook with friends and family without bumping into one another. With a clean white palate and glass french doors that lead to the backyard makes the space bright and cheerful. Well stocked kitchen with all the necessary cooking/serving items including cookware, pots, pans, plates, bowls, glasses, mugs, silverware, and 12 cup drip coffee maker. Dishwasher makes cleaning up a breeze!
The spacious primary bedroom with window seating, lounge chairs, chaise lounge and a queen bed has an adjoining ensuite. The remaining bedrooms have lots of natural light, small desk and lounge chairs that make for a peaceful retreat.
In total, there are four bedrooms to accommodate up to 8 guests during your stay, for easy planning, here are the bedroom layouts:
Main Bedroom: Queen size bed w/ ensuite bathroom and private porch
Second Bedroom: Queen size bed
Third Bedroom: Queen size bed
Fourth Bedroom: Full size bed
This home boasts two and a half bathrooms. The primary bedroom ensuite has double sinks and a tub/shower combo. The second full bath has a stand up shower with two shower heads and a handheld shower wand. The half bath powder room is on the first floor, convenient to everyone.
Relax on an expansive deck that has room for everyone! Enjoy your morning coffee or use the gas grill to make your favorite meal as the sun goes down.
Other things to get excited about:
-Inside the home, you will find hardwoods throughout the main and top floors with rugs in each room.
-Stay cool this summer with single zone central air on the first level and mini splits upstairs.
-Circular driveway can fit four to six cars and a side driveway to fit an additional car.
-New Samsung front loading washer / dryer upstairs next to all Bedrooms.
-Several stairs to enter the house, so it may not be the best rental for those with limited mobility.
Please keep in mind:
-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.
The Neighborhood:
Charming neighborhood around the corner from Chesterwood is within walking distance to beautiful nature trails, the Rockwell Museum and Main Street. This home is also a short drive from all the Berkshires has to offer. This location is only short drives to Tanglewood, Berkshire Botanical Garden, Stockbridge Bowl, West Stockbridge, Housatonic, Great Barrington, Lenox, Butternut, Lee, Shaker Village, and Jacob ' s Pillow.
Some of our favorite eating places are the Red Lion Inn (Stockbridge) , Once Upon A Table (Stockbridge) , Brava (Lenox), and Prairie Whale (Great Barrington)
Other Things to Note:
We look forward to welcoming you soon!
Standard rules like no smoking, no partying, and being respectful of the neighbors apply.
Bring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!
No sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.
*Damage caused by pets is not covered by the accidental damage waiver.

Classic Stockbridge Cottage is located in Glendale. Classic Stockbridge Cottage provides accommodation, featuring Air Conditioner, Wellness Facilities, Kitchen, among other amenities. This House features Air Conditioner, Wellness Facilities, Kitchen, to make your stay a comfortable one.

Classic Stockbridge Cottage has 4 Bedrooms , 2 Bathrooms, and max occupancy of 8 persons. The minimum rental for this property is 1 night, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Glendale has interesting places to visit. If you want to learn more about the House in Glendale, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

  • Air Conditioner
  • Parking
  • Pet Friendly
  • TV
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry

Policies

Event Policy
Event Policy No events allowed
Check-in
Check-in Check-in time starts at 4:00 pm minimum check-in age: 25
Check-out
Check-out Check-out before 11:00 am
Child Policy
Child Policy Children are welcome.
Pet Policy
Pet Policy Note from host: charge may apply pets allowed service animals are welcome, and are exempt from fees
Smoking Policy
Smoking Policy Smoking is not permitted
Other Policy
Other Policy 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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited property registration number c0197200870 safety features at this property include a fire extinguisher special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property accepts cash 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

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Reviews

Nancy F. Jun 13, 2025 12:18:41 AM
Summary: The house is just about perfect! We were able to get in quickly and many of the lights are intuitive - in logical places - so even though we didn't arrive till dusk, all was easy getting in.As we wandered and learned more about the house, we all marveled at the comfort. Chairs are comfortable, tables set in logical, easy reach, kitchen easily learnable. We enjoyed the art and the lack of sterility.We also enjoyed the nesting birds above the kitchen door. Mama was pretty cranky whenever we were in the dining area but I like to think that she got used to us and realized that we were all enchanted watching her come and go and feed her babies. We even saw one of them fledge! The second one was a bit later and we missed that one leaving but later that day, it was clear that the nest was empty. Thank you for the note on the door!I have two suggestions (?). One is that the master bedroom toilet has a loose rubber gasket which means that the toilet leaks slowly. Not a huge deal but pretty easily fixable, I believe.The other is that it might be a thought to put tall stakes as markers at the two large rocks on either side of the top of the driveway. By the time we left, we had them pretty much scoped out but still felt compelled to have someone outside the car to guide the driver. A couple of those thin orange rods might work well. We had three people in our party who have bum knees and so chose to use the upper entrance. Many thanks!!
James T. Jun 1, 2025 06:51:49 PM
Summary: This property had everything we needed - convenient location, clean and well-stocked kitchen, gas barbeque, plenty of room, wi-fi/TV, and easy check-in/check-out. Would definitely rent again. Thanks for the great accommodations and for facilitating our visit to Glendale and the surrounding area!
Michael C. May 5, 2025 09:46:32 AM
Summary: The house was spacious and in good shape. The location is great. Overall we had a great time. I agree with the description of the property, esp the warning that there a lot of stairs. The inside stairs to the 2nd floor are quite steep.
mary v. Oct 23, 2024 12:56:35 AM
Summary: House is great . It is very spacious and well stocked. We were agroup of 4 woman and enjoyed the fact that we could take short drives to restaurants and shopping. We visited the Shrine and the Norman Rockwell museum.
Sara M. Oct 20, 2024 07:20:33 AM
Summary: My husband and I stayed here while on our first trip to the Berkshires. The house has a warm, cozy feel while being big enough to accommodate a family. The hosts left us some tourist info that extremely helpful and helped us decide how to structure our days. Thank you for sharing your beautiful home with us!
Beverly P. Oct 11, 2024 10:07:45 PM
Summary: There were 3 couples who stayed at the house. It was easy to find and to get into. The door locks made it easy, as we did not need a key! The house was wonderful. Everything it advertised and more. Very comfortable and roomy. We enjoyed our stay.
Lynne S. Sep 27, 2024 04:05:45 AM
Summary: This was an annual get-together for the Seniors in our family. We all did just fine with the stairs! I appreciated all of the artwork and beautiful coffee table books. Comfy beds in all rooms! Updated and well-equipped kitchen and baths where a plus. Everything we wanted to see was well within 30 minutes driving time. The majority of sites being 5-10 minutes.A pleasant and relaxing reunion! Thank you, Lucas for your great communications. ⭐️⭐️⭐️⭐️⭐️, Lynne
Jeffrey S. Aug 19, 2024 06:56:08 AM
Summary: Beautifully maintained, a mile and a half from Stockbridge with easy access to the entire county. Very comfortable. Would definitely go back.
Genevieve D. May 20, 2024 01:15:31 AM
Summary: Beautiful property. Will definitely be back.
Brenda O. May 3, 2024 06:47:55 AM
Summary: The house was ideal for four mature women to enjoy. It felt like home. It was spacious, inviting, clean, comfortable, and stylish.

FAQ's

Is this Classic Stockbridge Cottage pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Classic Stockbridge Cottage have a swimming pool?

No, this Classic Stockbridge Cottage does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Classic Stockbridge Cottage?

Best-rates for the Classic Stockbridge Cottage starts from $512 per night with includes Internet, Parking, Pet Friendly, TV, Security/Safety, Bedding/Linens, Fireplace/Heating, Laundry, Air Conditioner, Wellness Facilities, Kitchen, Barbecue/Outdoor Cooking, Child Friendly, Balcony/Terrace, Sports/Activities with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

Is Classic Stockbridge Cottage a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Classic Stockbridge Cottage wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Classic Stockbridge Cottage has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Classic Stockbridge Cottage?

Based on the information reported by the owner or manager, the Classic Stockbridge Cottage indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Classic Stockbridge Cottage?

Based on the information reported by the owner or manager, details for the cancellation policy for the Classic Stockbridge Cottage are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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