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Pittsfield

Oct 20 - Oct 21 ·
2 guests

Pittsfield Vacation Rentals

Pittsfield
2 guests

Adults:

2

Children:

0

Child’s age:

Over 15 stays assessed to highlight the standout picks

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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

8. Lll

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

10. Clover Hill Farm & Country Inn

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
8.8
643 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
643 reviews
From US$ 153 / 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
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
  • 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
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

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

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

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

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!

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

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

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
  • 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

Lll Lll

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

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

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
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 centre
  • Sun terrace
9.7
144 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 centre
  • Sun terrace

Clover Hill Farm & Country Inn

9.7
144 reviews
From US$ 250 / night
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
9.6
33 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
33 reviews
From US$ 166 / night
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
9.8
21 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
21 reviews
From US$ 130 / night

Pittsfield Vacation Rentals with Private Pool

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

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
Econo Lodge Lee - Great Barrington Econo Lodge Lee - Great Barrington

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 centre
6.8
226 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 centre

Econo Lodge Lee - Great Barrington

6.8
226 reviews
From US$ 52 / night
Cozy Cabin In Stratton Mountain & Mount Snow 10Min Cozy Cabin In Stratton Mountain & Mount Snow 10Min

Cozy Cabin In Stratton Mountain & Mount Snow 10Min

Stratton Arlington Road 669
71.3 km (44.3 mi) from Pittsfield
121
  • Cookware/ Kitchen utensils
  • Free parking
  • Ironing facilities
  • Tea and coffee facilities
  • Heating
10
9 reviews
~ US$241 / night

Cozy Cabin In Stratton Mountain & Mount Snow 10Min

71.3 km (44.3 mi) from Pittsfield
121
  • Cookware/ Kitchen utensils
  • Free parking
  • Ironing facilities
  • Tea and coffee facilities
  • Heating

Cozy Cabin In Stratton Mountain & Mount Snow 10Min

10
9 reviews
From US$ 241 / night
The Retreat At Norwich Lake The Retreat At Norwich Lake

The Retreat At Norwich Lake

128 Norwich Lake
37.9 km (23.5 mi) from Pittsfield
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Table tennis
  • Terrace
9.1
30 reviews
~ US$395 / night

The Retreat At Norwich Lake

37.9 km (23.5 mi) from Pittsfield
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Table tennis
  • Terrace

The Retreat At Norwich Lake

9.1
30 reviews
From US$ 395 / night
1890 Capecod Farmhouse:Charming, Private, Spacious 1890 Capecod Farmhouse:Charming, Private, Spacious

1890 Capecod Farmhouse:Charming, Private, Spacious

1164 New York 212
77.4 km (48.1 mi) from Pittsfield
149
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Jacuzzi
  • Sun terrace
10
22 reviews
~ US$649 / night

1890 Capecod Farmhouse:Charming, Private, Spacious

77.4 km (48.1 mi) from Pittsfield
149
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Jacuzzi
  • Sun terrace

1890 Capecod Farmhouse:Charming, Private, Spacious

10
22 reviews
From US$ 649 / night
Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor

Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor

Corey Road 37
12.3 km (7.6 mi) from Pittsfield
47
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Fitness centre
  • Outdoor swimming pool
10
4 reviews
~ US$279 / night

Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor

12.3 km (7.6 mi) from Pittsfield
47
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Fitness centre
  • Outdoor swimming pool

Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor

10
4 reviews
From US$ 279 / 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

(643 Reviews)

 From 153$
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

(144 Reviews)

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

9.6 / 10

(33 Reviews)

 From 166$

Location