On Our Way Travel Pittsfield
Pittsfield
2 guests

Adults:

2

Children:

0

Child’s age:

Pittsfield

Oct 07 - Oct 08 ·
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. Elegant Pittsfield Home Near Downtown & Skiing!

3. Spacious Historic Home In The Berkshires!

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

Cheap Vacation Rentals in Pittsfield Massachusetts

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

8. Lll

9. Fall Fun In The Berkshires: Yard, Patio, Playset

10. Clover Hill Farm & Country Inn

Luxury Vacation Rentals Pittsfield

  • Guest favorite
Hotel Image Hotel Image

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
8.8
651 reviews
~ US$153 / 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

8.8
651 reviews
From US$ 153 / night
  • Top location
Hotel Image Hotel Image

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
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!

10
2 reviews
From US$ 356 / night
Hotel Image Hotel Image

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
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!

9
1 reviews
From US$ 289 / night

Cheap Vacation Rentals in Pittsfield Massachusetts

  • Great deal
Hotel Image Hotel Image

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 course
  • Patio

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 course
  • Patio

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

Hotel Image Hotel Image

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

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!

Hotel Image Hotel Image

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

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

Pet Friendly Vacation Rentals Pittsfield

Hotel Image Hotel Image

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
  • Jacuzzi

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
  • Jacuzzi

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

Hotel Image Hotel Image

Lll

8 Dan Fox Drive
4.5 km (2.8 mi) from city center
  • Free parking
  • Flat-screen TV
  • Tea and coffee facilities
  • Fitness centre
  • Jacuzzi

Lll

4.5 km (2.8 mi) from city center
  • Free parking
  • Flat-screen TV
  • Tea and coffee facilities
  • Fitness centre
  • Jacuzzi

Lll

Hotel Image Hotel Image

Fall Fun In The Berkshires: Yard, Patio, Playset

46 Lucille St
3.1 km (1.9 mi) from city center
143
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Heating
  • Fitness centre
  • Terrace

Fall Fun In The Berkshires: Yard, Patio, Playset

3.1 km (1.9 mi) from city center
143
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Heating
  • Fitness centre
  • Terrace

Fall Fun In The Berkshires: Yard, Patio, Playset

Vacation rentals near Pittsfield

Pittsfield Vacation Rentals Oceanfront

  • Best-rated
Hotel Image Hotel Image

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
9.7
141 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

9.7
141 reviews
From US$ 250 / night
Hotel Image Hotel Image

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
9.6
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

9.6
35 reviews
From US$ 166 / night
Hotel Image Hotel Image

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
9.6
18 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

9.6
18 reviews
From US$ 130 / night

Pittsfield Vacation Rentals with Private Pool

Hotel Image Hotel Image

Stylish Pine Plains Home Near Parks & Hiking!

17 Birch Dr
62.8 km (39.0 mi) from Pittsfield
84
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Flat-screen TV
  • Ironing facilities
  • Heating
10
7 reviews
~ US$119 / night

Stylish Pine Plains Home Near Parks & Hiking!

62.8 km (39.0 mi) from Pittsfield
84
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Flat-screen TV
  • Ironing facilities
  • Heating

Stylish Pine Plains Home Near Parks & Hiking!

10
7 reviews
From US$ 119 / night
Hotel Image Hotel Image

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
9.8
19 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

9.8
19 reviews
From US$ 130 / night
Hotel Image Hotel Image

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
9.2
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

9.2
49 reviews
From US$ 192 / night
  • Private beach
Hotel Image Hotel Image

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
9.5
27 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!

9.5
27 reviews
From US$ 302 / night
Hotel Image Hotel Image

Rustic-Chic Cottage W/ Yard & Grill - Near Hiking!

70.1 km (43.6 mi) from Pittsfield
125
  • Cookware/ Kitchen utensils
  • Car park
    Charges may apply
  • Flat-screen TV
  • Ironing facilities
  • Terrace
  • Garden area
9.2
14 reviews
~ US$93 / night

Rustic-Chic Cottage W/ Yard & Grill - Near Hiking!

70.1 km (43.6 mi) from Pittsfield
125
  • Cookware/ Kitchen utensils
  • Car park
    Charges may apply
  • Flat-screen TV
  • Ironing facilities
  • Terrace
  • Garden area

Rustic-Chic Cottage W/ Yard & Grill - Near Hiking!

9.2
14 reviews
From US$ 93 / night
Hotel Image Hotel Image

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
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

9.5
12 reviews
From US$ 95 / night
Hotel Image Hotel Image

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 course
  • Sun terrace
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 course
  • Sun terrace

Country Cottage With Large Yard, Fire Pit & Nature Views

9
25 reviews
From US$ 168 / night
Hotel Image Hotel Image

Econo Lodge Lee - Great Barrington

980 Pleasant Street
19.1 km (11.9 mi) from Pittsfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Tea and coffee facilities
  • Heating
  • Golf course
6.7
227 reviews
~ US$52 / night

Econo Lodge Lee - Great Barrington

19.1 km (11.9 mi) from Pittsfield
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Tea and coffee facilities
  • Heating
  • Golf course

Econo Lodge Lee - Great Barrington

6.7
227 reviews
From US$ 52 / 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

8.8 / 10

(651 Reviews)

 From 153$
Elegant Pittsfield Home Near Downtown & Skiing!

10.0 / 10

(2 Reviews)

 From 356$
Spacious Historic Home In The Berkshires!

9.0 / 10

(1 Reviews)

 From 289$
Clover Hill Farm & Country Inn

9.7 / 10

(141 Reviews)

 From 250$
Hibiscus Suite - Private Studio Apartment In Rhinebeck Village

9.6 / 10

(35 Reviews)

 From 166$

Location