Best Pittsfield Vacation Rentals
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Guest favorite
Berkshire Mountain Lodge
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Fitness centre
- Heated swimming pool
Nestled about a 10-minute drive from Museum Facsimiles Outlet Store, the 4-room Berkshire Mountain Lodge Pittsfield features a swimming pool along with a hot tub to help guests unwind. Offering a vending machine and a lift, this accommodation can be found in a ski part of Pittsfield.
Guests can stay active with hiking and ping-pong or relax in a Jacuzzi and an indoor pool on site. The availability of fitness classes, along with a fitness centre, ensures guests an active stay.
Berkshire Mountain Lodge
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Fitness centre
- Heated swimming pool
Berkshire Mountain Lodge
Nestled about a 10-minute drive from Museum Facsimiles Outlet Store, the 4-room Berkshire Mountain Lodge Pittsfield features a swimming pool along with a hot tub to help guests unwind. Offering a vending machine and a lift, this accommodation can be found in a ski part of Pittsfield.
Guests can stay active with hiking and ping-pong or relax in a Jacuzzi and an indoor pool on site. The availability of fitness classes, along with a fitness centre, ensures guests an active stay.
Spacious Historic Home In The Berkshires!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Heating
The 5-bedroom Spacious Historic Home In The Berkshires! Pittsfield offers proximity to such city sites as Unitarian Universalist Church of Pittsfield, located merely a 5-minute walk away. Providing guests with Wi-Fi and a car park, the welcoming villa is 3.3 km from First Baptist Church.
Spacious Historic Home In The Berkshires!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Heating
Spacious Historic Home In The Berkshires!
The 5-bedroom Spacious Historic Home In The Berkshires! Pittsfield offers proximity to such city sites as Unitarian Universalist Church of Pittsfield, located merely a 5-minute walk away. Providing guests with Wi-Fi and a car park, the welcoming villa is 3.3 km from First Baptist Church.
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Top location
Elegant Pittsfield Home Near Downtown & Skiing!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Terrace
Situated nearly a 25-minute walk from Mass Audubon Canoe Meadows Wildlife Sanctuary, the 5-bedroom Elegant Pittsfield Home Near Downtown & Skiing! offers guests to enjoy a terrace and barbecue. Providing guests with Wi-Fi and a car park, the property is around 3 km from Herman Melville's Arrowhead Historic House Museum.
Elegant Pittsfield Home Near Downtown & Skiing!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Terrace
Elegant Pittsfield Home Near Downtown & Skiing!
Situated nearly a 25-minute walk from Mass Audubon Canoe Meadows Wildlife Sanctuary, the 5-bedroom Elegant Pittsfield Home Near Downtown & Skiing! offers guests to enjoy a terrace and barbecue. Providing guests with Wi-Fi and a car park, the property is around 3 km from Herman Melville's Arrowhead Historic House Museum.
Cheap Pittsfield Vacation Rentals
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Great deal
Charming Cabin With Serene Lake Views For A Family Getaway Near Pittsfield, Massachusetts
- Cookware/ Kitchen utensils
- Air conditioning
- Heating
- Golf centre
- Golf course
- Patio
The 3-bedroom Charming Cabin With Serene Lake Views For A Family Getaway Near Pittsfield, Massachusetts is located within 7 km of Olivia's Overlook and welcomes its guests to enjoy canyoning, hiking, and horseback riding. Offering horse riding tours, this Pittsfield holiday home can accommodate up to 7 people.
Charming Cabin With Serene Lake Views For A Family Getaway Near Pittsfield, Massachusetts
- Cookware/ Kitchen utensils
- Air conditioning
- Heating
- Golf centre
- Golf course
- Patio
Charming Cabin With Serene Lake Views For A Family Getaway Near Pittsfield, Massachusetts
The 3-bedroom Charming Cabin With Serene Lake Views For A Family Getaway Near Pittsfield, Massachusetts is located within 7 km of Olivia's Overlook and welcomes its guests to enjoy canyoning, hiking, and horseback riding. Offering horse riding tours, this Pittsfield holiday home can accommodate up to 7 people.
Lake Views & Dock Access - Pittsfield Cottage!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Sun loungers
The 4-bedroom Lake Views & Dock Access - Pittsfield Cottage! is located around 6 km from the Your Berkshire Community Museum and provides canyoning for active guests. Located within a 10-minute drive of Lake Onota Village Park, this property provides Wi-Fi and parking.
Lake Views & Dock Access - Pittsfield Cottage!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Sun loungers
Lake Views & Dock Access - Pittsfield Cottage!
The 4-bedroom Lake Views & Dock Access - Pittsfield Cottage! is located around 6 km from the Your Berkshire Community Museum and provides canyoning for active guests. Located within a 10-minute drive of Lake Onota Village Park, this property provides Wi-Fi and parking.
Cozy Pittsfield Gem With Deck, Gazebo And Fireplace
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Laundry
- Skiing
- Terrace
Featuring horse riding tours to make your visit more entertaining, the 3-bedroom Cozy Pittsfield Gem With Deck, Gazebo And Fireplace villa is 4.7 km from Pontoosuc Lake. Guests can enjoy snow skiing and horseback riding at this accommodation, located about 15 minutes' drive from Museum Facsimiles Outlet Store.
Cozy Pittsfield Gem With Deck, Gazebo And Fireplace
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Laundry
- Skiing
- Terrace
Cozy Pittsfield Gem With Deck, Gazebo And Fireplace
Featuring horse riding tours to make your visit more entertaining, the 3-bedroom Cozy Pittsfield Gem With Deck, Gazebo And Fireplace villa is 4.7 km from Pontoosuc Lake. Guests can enjoy snow skiing and horseback riding at this accommodation, located about 15 minutes' drive from Museum Facsimiles Outlet Store.
Pet Friendly Vacation Rentals Pittsfield Massachusetts
13-Min Jiminy, Fave, Hot Tub, Lg Open Lr, Family
- Free parking
- Air conditioning
- Flat-screen TV
Located about 10 minutes' drive from Pittsfield State Forest, 13-Min Jiminy, Fave, Hot Tub, Lg Open Lr, Family Villa Pittsfield provides access to various tourist attractions in the vicinity. With a maximum capacity of 10 guests, the property offers private car parking.
13-Min Jiminy, Fave, Hot Tub, Lg Open Lr, Family
- Free parking
- Air conditioning
- Flat-screen TV
13-Min Jiminy, Fave, Hot Tub, Lg Open Lr, Family
Located about 10 minutes' drive from Pittsfield State Forest, 13-Min Jiminy, Fave, Hot Tub, Lg Open Lr, Family Villa Pittsfield provides access to various tourist attractions in the vicinity. With a maximum capacity of 10 guests, the property offers private car parking.
Berkshire Mountain Lodge
- Free parking
- Fitness centre
- Jacuzzi
Situated nearly a 10-minute drive from Pleasant Valley Sanctuary Wildlife Refuge, the 1-bedroom Lll Villa Pittsfield includes a swimming pool, as well as a hot tub to relax in. Featuring mountain views, the Pittsfield lodge invites guests to visit the 750 vertical foot mountain "Bousquet Ski Area", located only 1.5 km away.
Berkshire Mountain Lodge
- Free parking
- Fitness centre
- Jacuzzi
Berkshire Mountain Lodge
Situated nearly a 10-minute drive from Pleasant Valley Sanctuary Wildlife Refuge, the 1-bedroom Lll Villa Pittsfield includes a swimming pool, as well as a hot tub to relax in. Featuring mountain views, the Pittsfield lodge invites guests to visit the 750 vertical foot mountain "Bousquet Ski Area", located only 1.5 km away.
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Best-rated
Clover Hill Farm & Country Inn
- BBQ facilities
- Free parking
- Security
- Air conditioning
- Golf course
- Sun terrace
Situated 2.6 km from Pine Cobble Mountain, the 3-room Clover Hill Farm & Country Inn Williamstown villa offers guests to enjoy a sunbathing terrace, a picnic area, and a golf course. Featuring a Jacuzzi, the property is about 15 minutes' drive from Sweet Brook Farm.
A shared lounge is available on site, and hiking, cycling, and fisheries can be enjoyed within proximity of the Williamstown accommodation.
Clover Hill Farm & Country Inn
- BBQ facilities
- Free parking
- Security
- Air conditioning
- Golf course
- Sun terrace
Clover Hill Farm & Country Inn
Situated 2.6 km from Pine Cobble Mountain, the 3-room Clover Hill Farm & Country Inn Williamstown villa offers guests to enjoy a sunbathing terrace, a picnic area, and a golf course. Featuring a Jacuzzi, the property is about 15 minutes' drive from Sweet Brook Farm.
A shared lounge is available on site, and hiking, cycling, and fisheries can be enjoyed within proximity of the Williamstown accommodation.
Pittsfield Vacation Rentals Oceanfront
Hibiscus Suite - Private Studio Apartment In Rhinebeck Village
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Garden area
To enjoy your vacation in Rhinebeck, stay at the 18 m² Hibiscus Suite - Private Studio Apartment In Rhinebeck Village, which is around a 25-minute walk from Ferncliff Forest and about 6 km from the living Old Rhinebeck Aerodrome Aviation Museum. At this 1-bedroom apartment, Wi-Fi and parking are also provided.
Guests can also participate in badminton to add a touch of excitement to their stay.
Hibiscus Suite - Private Studio Apartment In Rhinebeck Village
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Garden area
Hibiscus Suite - Private Studio Apartment In Rhinebeck Village
To enjoy your vacation in Rhinebeck, stay at the 18 m² Hibiscus Suite - Private Studio Apartment In Rhinebeck Village, which is around a 25-minute walk from Ferncliff Forest and about 6 km from the living Old Rhinebeck Aerodrome Aviation Museum. At this 1-bedroom apartment, Wi-Fi and parking are also provided.
Guests can also participate in badminton to add a touch of excitement to their stay.
North Shire Lodge
- Picnic area/ Tables
- Free parking
- Housekeeping
- Air conditioning
- Ski pass vendor
- Pool with view
During the stay at North Shire Lodge Manchester, guests can indulge in hiking and skiing or visit Norman Rockwell Exhibition Art Gallery, located 6 km away. The 8-room villa provides a ski pass vendor, as well as a sunbathing terrace and a picnic area for an enjoyable stay.
North Shire Lodge
- Picnic area/ Tables
- Free parking
- Housekeeping
- Air conditioning
- Ski pass vendor
- Pool with view
North Shire Lodge
During the stay at North Shire Lodge Manchester, guests can indulge in hiking and skiing or visit Norman Rockwell Exhibition Art Gallery, located 6 km away. The 8-room villa provides a ski pass vendor, as well as a sunbathing terrace and a picnic area for an enjoyable stay.
The Innwoods - Studio Apartment 1
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Staying at the 23 m² The Innwoods - Studio Apartment 1 Tannersville, guests can visit Tannersville General Store, located around 700 metres away. At the apartment, Wi-Fi and parking are also provided.
The Innwoods - Studio Apartment 1
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
The Innwoods - Studio Apartment 1
Staying at the 23 m² The Innwoods - Studio Apartment 1 Tannersville, guests can visit Tannersville General Store, located around 700 metres away. At the apartment, Wi-Fi and parking are also provided.
Pittsfield Vacation Rentals with Private Pool
The Innwoods - Studio Apartment 2
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
To enjoy your vacation in Tannersville, stay at the 23 m² The Innwoods - Studio Apartment 2 Tannersville, which is approximately 10 minutes by car from Bear Creek Landing and 2.5 km from Plattekill Falls. This 1-bedroom apartment features Wi-Fi, along with a car park for guests travelling by car.
The Innwoods - Studio Apartment 2
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
The Innwoods - Studio Apartment 2
To enjoy your vacation in Tannersville, stay at the 23 m² The Innwoods - Studio Apartment 2 Tannersville, which is approximately 10 minutes by car from Bear Creek Landing and 2.5 km from Plattekill Falls. This 1-bedroom apartment features Wi-Fi, along with a car park for guests travelling by car.
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Private beach
New 3 Bedroom - Thoroughbred Farm & Lake Views!
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Live entertainment
Situated about 5 minutes' walk from Saratoga Lake, the 3-bedroom New 3 Bedroom - Thoroughbred Farm & Lake Views! Saratoga Springs villa is ideal for up to 6 guests. The property boasts a picnic area and a golf course, while Saratoga Lake Golf Club is 3.7 km away.
The Saratoga Springs property offers a nightclub and a casino for entertainment, as well as mini golf and billiard for sport lovers.
New 3 Bedroom - Thoroughbred Farm & Lake Views!
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Live entertainment
New 3 Bedroom - Thoroughbred Farm & Lake Views!
Situated about 5 minutes' walk from Saratoga Lake, the 3-bedroom New 3 Bedroom - Thoroughbred Farm & Lake Views! Saratoga Springs villa is ideal for up to 6 guests. The property boasts a picnic area and a golf course, while Saratoga Lake Golf Club is 3.7 km away.
The Saratoga Springs property offers a nightclub and a casino for entertainment, as well as mini golf and billiard for sport lovers.
Downtown Albany 1 Bed With Workstation On Maiden Lane
- Cookware/ Kitchen utensils
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Car park
Charges may apply
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Laundry
The 1-room Downtown Albany 1 Bed With Workstation On Maiden Lane Apartment is located 0.7 km from the indoor arena "Times Union Center" and 19 minutes' walk from the Schuyler Mansion State Historic Site. This apartment can hold up to 4 guests.
Downtown Albany 1 Bed With Workstation On Maiden Lane
- Cookware/ Kitchen utensils
-
Car park
Charges may apply
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Laundry
Downtown Albany 1 Bed With Workstation On Maiden Lane
The 1-room Downtown Albany 1 Bed With Workstation On Maiden Lane Apartment is located 0.7 km from the indoor arena "Times Union Center" and 19 minutes' walk from the Schuyler Mansion State Historic Site. This apartment can hold up to 4 guests.
Country Cottage With Large Yard, Fire Pit & Nature Views
- Picnic area/ Tables
- Free parking
- Security
- Air conditioning
- Golf centre
- Sun terrace
Nestled approximately 7 km from Lighthouse, the 1-bedroom Country Cottage With Large Yard, Fire Pit & Nature Views Saugerties is boasting a sunbathing terrace, a picnic area, and a golf course for guests' enjoyment. Located about 10 minutes' drive from Cantine Field Memorial Park, the holiday home provides Wi-Fi and private car parking.
Hiking and lawn tennis are among the various activities that are offered in the surrounding area.
Country Cottage With Large Yard, Fire Pit & Nature Views
- Picnic area/ Tables
- Free parking
- Security
- Air conditioning
- Golf centre
- Sun terrace
Country Cottage With Large Yard, Fire Pit & Nature Views
Nestled approximately 7 km from Lighthouse, the 1-bedroom Country Cottage With Large Yard, Fire Pit & Nature Views Saugerties is boasting a sunbathing terrace, a picnic area, and a golf course for guests' enjoyment. Located about 10 minutes' drive from Cantine Field Memorial Park, the holiday home provides Wi-Fi and private car parking.
Hiking and lawn tennis are among the various activities that are offered in the surrounding area.
Berkshire Riverfront Ski Cabin: Close To Hiking!
- Free parking
- Heating
Located approximately a 20-minute walk from Umpachene Falls Park, the 2-bedroom Berkshire Riverfront Ski Cabin: Close To Hiking! Mill River gives access to various tourist sites in the vicinity. Up to 5 guests can stay at this 1-bathroom villa, which offers hire for rent.
Hiking are possible in the area.
Berkshire Riverfront Ski Cabin: Close To Hiking!
- Free parking
- Heating
Berkshire Riverfront Ski Cabin: Close To Hiking!
Located approximately a 20-minute walk from Umpachene Falls Park, the 2-bedroom Berkshire Riverfront Ski Cabin: Close To Hiking! Mill River gives access to various tourist sites in the vicinity. Up to 5 guests can stay at this 1-bathroom villa, which offers hire for rent.
Hiking are possible in the area.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Pittsfield, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Berkshire Mountain Lodge |
8.6 / 10 (642 Reviews) |
From 164$ | |
| Spacious Historic Home In The Berkshires! |
9.0 / 10 (1 Reviews) |
From 289$ | |
| Elegant Pittsfield Home Near Downtown & Skiing! |
10.0 / 10 (2 Reviews) |
From 356$ | |
| Clover Hill Farm & Country Inn |
9.7 / 10 (131 Reviews) |
From 250$ | |
| Hibiscus Suite - Private Studio Apartment In Rhinebeck Village |
9.7 / 10 (35 Reviews) |
From 166$ |
Frequently Asked Questions
Which vacation rentals near downtown Pittsfield offer easy access to local attractions?
Elegant Pittsfield Home Near Downtown & Skiing features a central location for exploring local attractions like the Berkshire Museum. Other nearby options include Berkshire Mountain Lodge, perfect for a quick trip to downtown.
Visit downtown between 10 am and 3 pm for fewer crowds at popular spots like museums.
What are the best vacation rentals for families in Pittsfield?
Charming Cabin With Serene Lake Views and Cozy Pittsfield Gem With Deck provide family-friendly amenities. Both have outdoor space for children to play and are conveniently located near family activities.
Choose rentals with kitchens to prepare meals, saving money on dining out when traveling with kids.
Which vacation rentals near historic districts in Pittsfield enhance the local experience?
Spacious Historic Home In The Berkshires and Berkshire Riverfront Ski Cabin place you near the historic charm of Pittsfield. These rentals let you explore nearby historic sites, ensuring a culturally rich stay.
Plan a visit to the nearby Barrington Stage Company for engaging local theater performances.
Are there vacation rentals with hot tubs in Pittsfield?
Look at the 13-Min Jiminy, Fave, Hot Tub, Lg Open Lr, Family for a cozy retreat complete with a hot tub. This is perfect for relaxation after a long day of exploring.
Book off-peak to enjoy your hot tub in a quieter setting, away from weekend crowds.
Which vacation rentals offer beautiful views in Pittsfield?
New 3 Bedroom - Thoroughbred Farm & Lake Views and Country Cottage With Large Yard, Fire Pit & Nature Views boast stunning scenery and outdoor settings. Both rentals allow you to enjoy the natural beauty of the Berkshires.
Early morning is the best time to capture beautiful sunrise views; take advantage of coffee on the patio.
What budget-friendly vacation rentals are available in Pittsfield?
Downtown Albany 1 Bed With Workstation On Maiden Lane offers affordable options without sacrificing comfort. Additionally, The Innwoods - Studio Apartment 1 and 2 provide reasonable rates for budget-conscious travelers.
Booking on weekdays can yield lower rates and more availability in these budget-friendly rentals.
Which vacation rentals are pet-friendly in Pittsfield?
Clover Hill Farm & Country Inn and Cozy Pittsfield Gem With Deck welcome pets, making it easy to travel with furry friends. Always check the pet policy for any extra fees.
Pack a favorite blanket or toy for your pet to help them adjust to the new environment.
What local events should I look for when planning my trip to Pittsfield?
The Pittsfield Fourth of July Parade is a must-see and celebrates with community spirit and local flair. Other events include the Berkshire Mountain Film Festival, highlighting regional cinema talent.
Book your vacation rental early for peak event times to ensure the best options.
How can I explore the best of Pittsfield during my stay?
Use public transportation or rent a bike to explore the city's parks and cultural landmarks. Nearby attractions include the Berkshire Museum and Hancock Shaker Village.
Purchase a local transit pass for unlimited rides, making it easier to get around without a car.
What's the best time of year to visit Pittsfield?
Visiting in autumn allows you to enjoy stunning fall foliage and local harvest festivals. Spring is also nice, with blooming gardens and mild weather.
Check local calendars for seasonal produce markets; they often have local crafts too.