A rare find — the foosball table is waiting for you.
Centrally-located
You're never far from where you need to be with this convenient location.
Discover nearby landmarks
Walk to Berkshire Museum
5 bedrooms3+ bathroomsSleeps 10
Popular amenities
Onsite parking available
Kitchen
Washing machine
Air-conditioning
Barbecue grill
Deck or patio
Rooms & beds
5 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Bedroom 3
1 Queen Bed
Bedroom 4
1 Single Bed
Bedroom 5
1 Double Bed
3 bathrooms, 1 half bathroom
Full Bathroom
Full Bathroom
Full Bathroom
Half Bathroom
Spaces
Deck or patio
Porch or lanai
Kitchen
Separate dining area
Garden
About this property
Elegant Pittsfield Home Near Downtown & Skiing!
Experience a fun-filled group getaway at this Pittsfield vacation rental! Named 'The Duchess of Pomeroy' for its charming historical features, this 5-bedroom, 3.5-bath home boasts a furnished deck, a foosball table, and a screened porch that's perfect for enjoying morning coffee or evening cocktails. Looking to venture out? Catch live music at Tanglewood or shred the slopes at Bousquet Mountain Ski Area. Afterward, cook a meal on the grill and dine al fresco. A memorable stay awaits!
-- THE PROPERTY --
C0344732360 | Gas Grill | 8 Mi to Tanglewood | Fully Equipped Kitchen w/ Food | 2,718 Sq Ft
Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Twin Bed | Bedroom 5: Full Bed | Additional Sleeping: Twin Rollaway Cot
OUTDOOR LIVING: Private yard, screened porch, outdoor dining areas, deck, picnic supplies w/ cooler blanket, ice packs, recyclable cutlery, bug spray & umbrella INDOOR LIVING: Smart TV, laptop-friendly workspace, dining table, board games, books, 4-in-1 game table (foosball, ping-pong, air hockey, billiards), fireplace, piano, 2 staircases, butler's pantry KITCHEN: Cooking basics, dishwasher, blender, Keurig & drip coffee makers, complimentary coffee beans, pods & tea, coffee grinder, 2 Crockpots, dishware & flatware, microwave, ice maker, toaster, spices, water filter GENERAL: Free WiFi (146.6 Mbps), A/C units (every bedroom + living room), central heating, towels/linens, hair dryer, hangers, in-unit washer/dryer, complimentary toiletries, iron/board, distilled water (for iron) FAQ: Garage not available for guest use ACCESSIBILITY: 3-story home, exterior stairs required to enter, all bedrooms on 2nd & 3rd floors PARKING: Driveway (4 vehicles), free street parking
-- THE LOCATION --
ATTRACTIONS: Colonial Theatre (0.4 miles), Berkshire Museum (0.5 miles), Kidding Around Consignment (1 mile), Lake Onota (3 miles), Pittsfield State Forest (6 miles), Tanglewood (8 miles), TurnPark Art Space (11 miles), Notchview Nature Preserve (14 miles), Clark Art Institute (21 miles), Mohawk Trail (36 miles) RESTAURANTS: District Kitchen & Bar (0.6 miles), Thistle & Mirth (0.6 miles), King Kone (0.6 miles), Crust Pizza (0.6 miles), Trattoria Rustica (0.7 miles), Dottie's Coffee Lounge (1 mile), La Fogata (2 miles), Proprietor's Lodge (4 miles) SKI RESORTS: Bousquet Mountain Ski Area (4 miles), Jiminy Peak Mountain Resort (12 miles) AIRPORTS: Albany International Airport (43 miles), Bradley International Airport (59 miles), Hartford–Brainard Airport (65 miles)
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- POLICIES --
- No smoking or vaping of any kind - No pets allowed - No events, parties, or large gatherings - No candles or incense inside the house. A citronella candle outside is allowed and found on the back deck to help shoo away mosquitoes - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This 3-story home requires exterior stairs to enter. All bedrooms are located on the 2nd and 3rd floors and require additional interior stairs to access - NOTE: This property sleeps 9 guests in 5 beds, with room for 10 total by using the twin rollaway cot - NOTE: The garage is not available for guest use - NOTE: WiFi speed: 146.6 Mbps download, 17.1 Mbps upload, 29ms latency - NOTE: The owner provides milk, fruit, bread, butter, peanut and almond butter, jam, and various coffee and teas. Various staples are also provided in the pantry. Let the Guest Contact know of any food allergies in your group so the food available can be adjusted to your greatest welfare
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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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Pittsfield
Pittsfield is home to this holiday home. Guido's Marketplace and Lee Premium Outlets are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Canoe Meadows Wildlife Sanctuary and Pleasant Valley Wilderness Sanctuary. Berkshire Museum and Lichtenstein Center for the Arts are also worth visiting.
Lichtenstein Center for the Arts - 13 min walk - 1.1 km
Barrington Stage Company - 16 min walk - 1.4 km
Getting around
Pittsfield Intermodal Transportation Center - 16 min walk
Pittsfield, MA (PSF-Pittsfield Municipal) - 8 min drive
Restaurants
Burger King - 9 min walk
Dunkin' - 9 min walk
Dunkin' - 11 min walk
Angelina's Subs - 13 min walk
RJ’s - 13 min walk
Frequently asked questions
Is Elegant Pittsfield Home Near Downtown & Skiing! pet-friendly?
No, only service animals are welcome at the property.
How much does it cost to stay at Elegant Pittsfield Home Near Downtown & Skiing!?
As of 5 Jun, 2026, prices found for a 1-night stay for 2 adults at Elegant Pittsfield Home Near Downtown & Skiing! on 4 Jan, 2027 start from S$805, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Elegant Pittsfield Home Near Downtown & Skiing!?
On-site parking is available at the property.
What time is check-in at Elegant Pittsfield Home Near Downtown & Skiing!?
Check-in begins at 3:00 PM.
What time is check-out at Elegant Pittsfield Home Near Downtown & Skiing!?
Checkout is at 11:00 AM.
Where is Elegant Pittsfield Home Near Downtown & Skiing! located?
Situated in Pittsfield, this holiday home is within a 10-minute walk of Colonial Theater, Berkshire Athenaeum and Berkshire Museum. Lichtenstein Center for the Arts and Housatonic River are also within 15 minutes. Pittsfield Intermodal Transportation Center is 16 minutes by foot.
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We were very happy with our stay. Everything was as it appeared on the listing. House was clean, had a great layout for what we needed and owner was communicative and very knowledgeable about the area.
We truly enjoyed our week in Pittsfield and the Berkshires. The kitchen was extremely well-stocked with every appliance imaginable and access to a full pantry. Loved the location. Gas fireplace was an added benefit. Rooms, bathrooms and closet space were perfect. Definitely recommend!
We stayed at this house for extended weekend while visiting Tanglewood. The entire property is very charming, elegant, spacious, and well equipped. It's located at a beautiful, quiet neighborhood. We absolutely loved our stay at this house. The property owner was very nice and very helpful with our every need. We will definitely come back soon!!!
A wonderful property, centrally located and stocked with anything you might need.
Even though it was early in the season there was a decorated tree, other festive decor right down to stockings for the children!
The property was interesting . I booked this for a corporate gathering. For us the Duchess provided a great back drop for our discussions and meetings . It made us all feel more connected. Ironically the many doors of the house that connected rooms together in interesting ways was a symbol of all the channels of communication we need to leave open to work better together. The dinning room was a great size for us to work and play card games. Would book again for sure.
Charming lovely home with a wonderful and accommodating host!
This lovely home in Pittsfield, Mass. had a special charm all of its own. It was located in a quaint small town within walking distance. The host could not be more accommodating. Everything that anyone could possibly need was available. She even offered to buy baby gates for my young grandchildren. There were many toys for them to play with. The pantry and refrigerator were stocked with food necessities that were available for our use. She bought chocolate chip cookies for them when we arrived. When we checked out of the house my granddaughter left a small stuffed animal and the host called me to let me know. She promptly offered to mail it and immediately went to the post office to do so. We appreciated everything so much and we had a very enjoyable stay!
Eileen W.
Stayed 3 nights in Aug 2025
From a partner site
10/10 Excellent
Stacy
7 Oct, 2024
All the Comforts of Home!
Our group of three families, including four young children, had a wonderful fall stay at The Duchess! The space was perfect for a group of this size, and we so appreciated the family-friendly amenities like booster seats and toys. The house is lovely, with many interesting and eclectic decor touches. My son, age 3, took to wandering the housing pointing and exclaiming, "art!" The rooms were spacious, comfortable, and well-appointed. We also appreciated the refrigerator and pantry staples provided. It felt like staying at a friend's home prepped with us in mind rather than a rental property. The location is great—walking distance from town and a short drive to lots of local events and attractions. We didn't require much support from the owners, but they did check in and provided timely responses both before and during our stay. We would definitely come back and would highly recommend!
This beautiful old home on a nice street is a pleasure to stay in. The whole house is full of light and little treasures to entertain you. Fine china and a set of silverware in well appointed pantry and kitchen- chef’s dream - we ate out! It’s a bit of a maze with front and back stairs that kids would have a blast with. Also a fuss all table and little backyard. All bedrooms are up stairs with the 5th another 15 steps up….. a bit of a strain on old knees but we prevailed! Beds were comfortable. Lots of extras and a very hospitable host. Recommend this home for small family or friend gatherings.
Came to a wedding in Lenox and stayed for a long weekend. Very charming property with lots of amenities and all the things you need like washing detergent / refuse sacks / well stocked kitchen.
Terrifically maintained, updated, spacious, clean….lots of room for an extended family of 9.
Excellent host/manager; very responsive!!
Close to Tanglewood, Lenox, etc
We loved our stay and hope to return.
We highly recommend this home💕
We had a great time at this house. The house was so cute and clean. It was filled with everything you could need for a comfortable stay (kitchen equipment, laundry, games, etc.). Communication with property management was so easy and helpful and they were very generous with extra goodies. The house is in a perfect location for exploring neighboring cities and hosting a large group.
The property was great! However, the highlight was the accommodations of the homeowner, Carolyn, and the property manager, Danielle. We were lucky enough to be the first guests, and they went above and beyond to ensure that the stay was enjoyable. Being a crew that is on the road a majority of the year, we were able to help communicate improvements to the property for ourselves and future guests. They were extremely willing to listen to suggestions, and made sure that we were taken care of. We had a great time. The location was great, the nearby ammenities were plentiful, and the home was relaxing. We made full use of the grill, very well equipped kitchen, and very roomy home. It accommodated the 4 of us with absolutely no problems at all. I can’t say enough about the home, and the accommodations. Everything went as smooth as you could hope for, especially with it being the first time the home was rented. If you are looking for a great place to stay around the Pittsfield, MA area, this is the place!
Owner and management have done a fantastic job making this historic property (with updates that do not diminish its unique characteristics) a relaxing, comfortable, well-equipped place for family and friends. Great jumping off spot for festivals, museums, and biking etc. Great linens and small touches throughout.
My family has made an annual tradition of attending James Taylor’s 4th of July concert at Tanglewood and this year our group has grown to 10 and we we’re looking for a local place to stay at the last minute. Fortunately we came across the Duchess of Pomeroy on VRBO and it proved to be a wonderful home base only 15 minutes from the venue. The owner Danielle was super-accommodating and reached out to me in advance of our stay to see if our group had any special needs or requirements. While I got the impression this was their inaugural rental, you would never know it by the accommodations on-site. We had everything we could ask for and more. The kitchen and refrigerator were stocked with drinks, fresh fruits, snacks and muffins from a local bakery. Plenty of games available as well as a multi-use game table (foosball/air hockey/tennis/pool) to keep the kids entertained. The “Duchess” is a charmingly restored home from the early 1800’s boasting 5 bedrooms, 3+ baths and plenty of space to sleep our group of 10 with a fold-out bed. We particularly enjoyed the screened in porch for morning coffee and evening cocktails and the nice deck out back with a table, chairs and a gas grill. A/C units throughout the house kept us cool when needed. As we wrapped up our stay we all agreed that the Duchess of Pomeroy would make a great addition to our annual trek to the Berkshires. Looking forward to a reunion in 2023!