Pittsfield
2 guests

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Pittsfield

Nov 09 - Nov 10 ·
2 guests

Pittsfield Vacation Rentals

Pittsfield
2 guests

Adults:

2

Children:

0

Child’s age:

Over 15 stays assessed to highlight the standout picks

Navigation

1. Berkshire Mountain Lodge

2. Spacious Historic Home In The Berkshires!

3. Elegant Pittsfield Home Near Downtown & Skiing!

4. Charming Cabin With Serene Lake Views For A Family Getaway Near Pittsfield, Massachusetts

Cheap Pittsfield Vacation Rentals

5. Lake Views & Dock Access - Pittsfield Cottage!

6. Cozy Pittsfield Gem With Deck, Gazebo And Fireplace

7. 13-Min Jiminy, Fave, Hot Tub, Lg Open Lr, Family

Pet Friendly Vacation Rentals Pittsfield Massachusetts

8. Berkshire Mountain Lodge

9. Clover Hill Farm & Country Inn

10. Hibiscus Suite - Private Studio Apartment In Rhinebeck Village

Best Pittsfield Vacation Rentals

  • Guest favorite
Berkshire Mountain Lodge Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr
4.6 km (2.9 mi) from city center
  • 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.

8.6
642 reviews
~ US$164 / night

Berkshire Mountain Lodge

4.6 km (2.9 mi) from city center
  • 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.

8.6
642 reviews
From US$ 164 / night
Spacious Historic Home In The Berkshires! Spacious Historic Home In The Berkshires!

Spacious Historic Home In The Berkshires!

140 Bartlett Ave
0.9 km (0.6 mi) from city center
307
  • 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.

9
1 reviews
~ US$289 / night

Spacious Historic Home In The Berkshires!

0.9 km (0.6 mi) from city center
307
  • 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.

9
1 reviews
From US$ 289 / night
  • Top location
Elegant Pittsfield Home Near Downtown & Skiing! Elegant Pittsfield Home Near Downtown & Skiing!

Elegant Pittsfield Home Near Downtown & Skiing!

140 Pomeroy Ave
0.9 km (0.6 mi) from city center
253
  • 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.

10
2 reviews
~ US$356 / night

Elegant Pittsfield Home Near Downtown & Skiing!

0.9 km (0.6 mi) from city center
253
  • 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.

10
2 reviews
From US$ 356 / night

Cheap Pittsfield Vacation Rentals

  • Great deal
Charming Cabin With Serene Lake Views For A Family Getaway Near Pittsfield, Massachusetts Charming Cabin With Serene Lake Views For A Family Getaway Near Pittsfield, Massachusetts

Charming Cabin With Serene Lake Views For A Family Getaway Near Pittsfield, Massachusetts

Lake Rd
7.2 km (4.5 mi) from city center
186
  • 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

7.2 km (4.5 mi) from city center
186
  • 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! Lake Views & Dock Access - Pittsfield Cottage!

Lake Views & Dock Access - Pittsfield Cottage!

97 Narragansett Ave
5.6 km (3.5 mi) from city center
186
  • 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!

5.6 km (3.5 mi) from city center
186
  • 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 Cozy Pittsfield Gem With Deck, Gazebo And Fireplace

Cozy Pittsfield Gem With Deck, Gazebo And Fireplace

10 Lawrence Dr, Pittsfield, Ma 01201, Usa
4.9 km (3.0 mi) from city center
177
  • 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

4.9 km (3.0 mi) from city center
177
  • 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 13-Min Jiminy, Fave, Hot Tub, Lg Open Lr, Family

13-Min Jiminy, Fave, Hot Tub, Lg Open Lr, Family

3 Algonquin St
5.3 km (3.3 mi) from city center
210
  • 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

5.3 km (3.3 mi) from city center
210
  • 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 Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Drive
4.5 km (2.8 mi) from city center
  • 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

4.5 km (2.8 mi) from city center
  • 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.

Vacation rentals near Pittsfield

  • Best-rated
Clover Hill Farm & Country Inn Clover Hill Farm & Country Inn

Clover Hill Farm & Country Inn

249 Adams Road
28.8 km (17.9 mi) from Pittsfield
  • 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.

9.7
131 reviews
~ US$250 / night

Clover Hill Farm & Country Inn

28.8 km (17.9 mi) from Pittsfield
  • 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.

9.7
131 reviews
From US$ 250 / night

Pittsfield Vacation Rentals Oceanfront

Hibiscus Suite - Private Studio Apartment In Rhinebeck Village Hibiscus Suite - Private Studio Apartment In Rhinebeck Village

Hibiscus Suite - Private Studio Apartment In Rhinebeck Village

36 Orchard Street
79.2 km (49.2 mi) from Pittsfield
18
  • 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.

9.7
35 reviews
~ US$166 / night

Hibiscus Suite - Private Studio Apartment In Rhinebeck Village

79.2 km (49.2 mi) from Pittsfield
18
  • 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.

9.7
35 reviews
From US$ 166 / night
North Shire Lodge North Shire Lodge

North Shire Lodge

97 Main Street
75.4 km (46.9 mi) from Pittsfield
  • 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.

9.4
49 reviews
~ US$192 / night

North Shire Lodge

75.4 km (46.9 mi) from Pittsfield
  • 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.

9.4
49 reviews
From US$ 192 / night
The Innwoods - Studio Apartment 1 The Innwoods - Studio Apartment 1

The Innwoods - Studio Apartment 1

6014 Main Street 3
78.3 km (48.6 mi) from Pittsfield
23
  • 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.

9.5
17 reviews
~ US$130 / night

The Innwoods - Studio Apartment 1

78.3 km (48.6 mi) from Pittsfield
23
  • 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.

9.5
17 reviews
From US$ 130 / night

Pittsfield Vacation Rentals with Private Pool

The Innwoods - Studio Apartment 2 The Innwoods - Studio Apartment 2

The Innwoods - Studio Apartment 2

6014 Main Street 4
78.3 km (48.6 mi) from Pittsfield
23
  • 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.

9.8
15 reviews
~ US$130 / night

The Innwoods - Studio Apartment 2

78.3 km (48.6 mi) from Pittsfield
23
  • 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.

9.8
15 reviews
From US$ 130 / night
  • Private beach
New 3 Bedroom - Thoroughbred Farm & Lake Views! New 3 Bedroom - Thoroughbred Farm & Lake Views!

New 3 Bedroom - Thoroughbred Farm & Lake Views!

10 Brock Drive
74.2 km (46.1 mi) from Pittsfield
  • 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.

9.5
26 reviews
~ US$302 / night

New 3 Bedroom - Thoroughbred Farm & Lake Views!

74.2 km (46.1 mi) from Pittsfield
  • 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.

9.5
26 reviews
From US$ 302 / night
Downtown Albany 1 Bed With Workstation On Maiden Lane Downtown Albany 1 Bed With Workstation On Maiden Lane

Downtown Albany 1 Bed With Workstation On Maiden Lane

37 Maiden Lane
47.0 km (29.2 mi) from Pittsfield
  • Cookware/ Kitchen utensils
  • 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.

9.5
12 reviews
~ US$95 / night

Downtown Albany 1 Bed With Workstation On Maiden Lane

47.0 km (29.2 mi) from Pittsfield
  • 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.

9.5
12 reviews
From US$ 95 / night
Country Cottage With Large Yard, Fire Pit & Nature Views Country Cottage With Large Yard, Fire Pit & Nature Views

Country Cottage With Large Yard, Fire Pit & Nature Views

3 Dave Elliot Road
68.9 km (42.8 mi) from Pittsfield
7
  • 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.

9
25 reviews
~ US$168 / night

Country Cottage With Large Yard, Fire Pit & Nature Views

68.9 km (42.8 mi) from Pittsfield
7
  • 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.

9
25 reviews
From US$ 168 / night
Berkshire Riverfront Ski Cabin: Close To Hiking! Berkshire Riverfront Ski Cabin: Close To Hiking!

Berkshire Riverfront Ski Cabin: Close To Hiking!

38.2 km (23.7 mi) from Pittsfield
102
  • 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.

10
6 reviews
~ US$252 / night

Berkshire Riverfront Ski Cabin: Close To Hiking!

38.2 km (23.7 mi) from Pittsfield
102
  • 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.

10
6 reviews
From US$ 252 / night

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.

Tip:

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.

Tip:

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.

Tip:

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.

Tip:

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.

Tip:

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.

Tip:

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.

Tip:

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.

Tip:

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.

Tip:

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.

Tip:

Check local calendars for seasonal produce markets; they often have local crafts too.

Location