Pittsfield, MA Vacation Rentals

Discover vacation rentals, homes, and villas in Pittsfield, MA for an upcoming trip, whether for leisure or work. Every home is curated and professionally managed, offering more space, comfort, and flexibility for your trip. Along with premium amenities like 24/7 local support and high-speed Wi-Fi, many homes are equipped with features to suit different travel styles, group sizes, and budgets. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can earn and redeem points on every stay.

3 Vacation Rentals in Pittsfield

Elegant Pittsfield Home Near Downtown & Skiing!

Pittsfield, MA, US
5 Bedrooms 10 Guests
Jan 1 - 31
$565 night

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 -- Property Manager 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 Licence number: C0344732360

Spacious Historic Home in the Berkshires!

Pittsfield, MA, US
5 Bedrooms 9 Guests
Sep 15 - 17
$224 night

Just minutes from downtown Pittsfield and surrounded by the beauty of the Berkshires is this lovely 5-bedroom, 2-bathroom vacation rental! Immerse yourself in the arts, wander around history, take a hike, or enjoy the local bites — all possible from this convenient location. After your day around town, come back to this home and sit and enjoy a show in front of the fireplace, take a soak in the soaker tub, or whip up a delicious meal in the large kitchen. -- THE PROPERTY -- MassTaxConnect ID #C0404362360 | 7 Mi to Tanglewood | Grill | Covered Porch Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Full Bed | Bedroom 4: Queen Bed | Bedroom 5: Twin Bed INDOOR LIVING: Fireplace, Smart TV, dining table, ceiling fans, board games, books, laptop friendly, soaker tub KITCHEN: Refrigerator, stove/oven, microwave, dishwasher, drip coffee maker, toaster, dishware & flatware, spices, cooking basics GENERAL: Free WiFi, washer & dryer, towels, linens, complimentary toiletries, central heat, window A/C units, keyless entry, hair dryer, hangers, trash bags/paper towels FAQ: 3 exterior security cameras (facing out), stairs are required, pet fee (paid pre-trip, dogs only, 2 max) PARKING: Driveway (2 vehicles), street parking (first-come, first-served) -- THE LOCATION -- THE ARTS: Colonial Theatre (0.6 miles), Barrington Stage Company (1 mile), Boston Symphony Orchestra (7 miles), Shakespeare & Company (7 miles), Tanglewood Performing Arts (8 miles), Kripalu Center For Yoga & Health (9 miles), Jacob's Pillow (19 miles), Aston Magna Music Festival (20 miles), Albany Berkshire Ballet (38 miles) MUSEUMS: Berkshire Art Museum (0.4 miles), Herman Melville's Arrowhead (2 miles), The Mount - Edith Wharton’s Home (9 miles), Animagic Museum of Animation (10 miles), Norman Rockwell Museum (13 miles), MASS MoCA (21 miles), Clark Art Institute & Museum (21 miles) OPT OUTSIDE: Burbank Park (1 mile), Pontoosuc Lake (3 miles), Wahconah Falls State Park (8 miles), Mount Greylock State Reservation Visitor Center (9 miles), Ashmere Lake (10 miles), Monument Mountain (16 miles) SUMMER ACTIVITIES: Pittsfield Suns at Wahconah Park (1 mile), Hancock Shaker Village (4 miles), Mass Audubon's Pleasant Valley Wildlife Sanctuary (5 miles) AIRPORT: Albany International Airport (47 miles) -- REST EASY WITH US -- Property Manager 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 - Dog friendly w/ $100 fee (+ fees & taxes, 2 max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs for access - NOTE: Your safety matters. This property features a Ring Doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed. This property also features 2 exterior security cameras: 1 camera is located on the front porch facing the porch and front yard/driveway, and 1 camera is on the back patio facing the patio and backyard. The cameras are outward facing and do not look into interior spaces

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Lenox, MA, US
3 Bedrooms 6 Guests
Sep 15 - 17
$308 night

Situated in the heart of the Berkshires, this 3-bed, 2-bath vacation rental offers a modern living space, a large yard and an ideal location near many attractions. Adventure seekers will enjoy easy access to the Appalachian Trail and Catamount Ski Resort, music fans can catch the Boston Symphony Orchestra (BSO) at Tanglewood and theater lovers will be minutes from Shakespeare & Co and Barrington Stage Co. No matter what you’re seeking, this Lenox home will offer something nearby to enjoy! -- THE PROPERTY -- MassTaxConnect ID C0219571520 | 2,457 Sq Ft | Off-Street Parking | 2 Mi to Appalachian Trail Bedroom 1: King Bed | Bedroom 2: 2 Extra Long Twin Beds | Bedroom 3: 2 Extra Long Twin Beds | Family Room: Sleeper Sofa KITCHEN: Fully equipped, cooking basics, spices, coffee maker, blender, dishwasher, Crockpot, microwave, high-chair, wooden cabinets INDOOR LIVING: Furnished sunroom, flat-screen smart cable TV, DVD player, books, hardwood floors, decorative fireplace, 6-person dining table, 4-person glass table OUTDOOR LIVING: Large private yard, outdoor seating, Weber gas grill GENERAL: Free WiFi, towels/linens, toiletries, ceiling fans, hair dryer, keyless entry, first aid kit, window air conditioning units in each bedroom, portable air conditioning unit in living area PARKING: Garage (2 small vehicles), driveway (4 vehicles) -- THE LOCATION -- MUSIC & THEATRE: Shakespeare and Company (3.0 miles), Tanglewood Music Center (3.7 miles), Boston Symphony Orchestra (3.7 miles) Jacob’s Pillow (15.0 miles) POPULAR ATTRACTIONS: Kripalu Center for Yoga & Health (4.6 miles), Norman Rockwell Museum (8.8 miles), Berkshire Botanical Gardens (7.9 miles), Cranwell Spa & Golf Resort (3.7 miles) OUTDOOR ACTIVITIES: Appalachian Trail (11.2 miles), Pleasant Valley Wildlife Sanctuary (2.1 miles), Lenox Mountain (8.2 miles), Sandy Beach at Laurel Lake (5.4 miles), October Mountain State Forest (5.4 miles), Woods Pond (4.8 miles), Kennedy Park (2.7 miles), Stockbridge Bowl (5.6 miles) WINTER ACTIVITIES: Catamount Ski Area (23.4 miles), Bousquet Ski Area (5.1 miles), Ski Butternut (16.6 miles), Otis Ridge (18.9 miles) NEARBY CITIES: Lenox Center (2.3 miles), Great Barrington (15.8 miles), Stockbridge (9.0 miles), Pittsfield (7.7 miles), Sheffield (22.1 miles), Williamstown (27 miles) AIRPORTS: Albany International Airport (49.5 miles), Bradley International Airport (71.1 miles) -- REST EASY WITH US -- Property Manager 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 - No pets allowed - No events, parties or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: Additional post-stay fines will be imposed if travelers exceed the maximum occupancy of 6 Licence number: C0219571520;C0219571520

Vacation Rentals in Pittsfield by Amenities & Features

More space, more privacy, more points with every home rental.

What makes Homes & Villas by Marriott Bonvoy a unique home rental experience? Unlike other home rental sites like AirBNB, when you book a vacation rental with Homes & Villas by Marriott Bonvoy you always have the whole place to yourself. Plus, as a member of Marriott Bonvoy, you can earn points towards free nights with every stay.

Vacation Rentals Near Pittsfield

Saved Home Image
Sign in or join now to view and save the homes you love