Vacation rentals in Pittsfield - HomeToGo base64Hash Vacation rentals in Pittsfield - HomeToGo

Vacation rentals in Pittsfield

Browse 197 available vacation homes and compared across 8 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • House
    • Apartment
    • Pension

  • Distance to center

    • 1 mi
    • 2 mi
    • 3 mi

  • Rating

    • 4.5+
    • 4+

  • Services

    • WiFi
    • Air conditioning
    • Parking
    • Kitchen
    • TV
    • Pool
    • Washing machine
    • Dishwasher
    • Microwave
    • Fireplace
    • Yard
    • Balcony/patio
    • Hot tub
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals in Pittsfield

Discover your ideal Pittsfield vacation rental with real-time comparisons of 197 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Condo Pittsfield
Condo ∙ 8 guests ∙ 3 bedrooms

Children-friendly beautiful condo with BBQ, pool & terrace | Mountain view | Ski nearby | Dogs allowed

Pittsfield, Berkshire County, Massachusetts, United States
This family-friendly condo in Pittsfield features a kitchen, fireplace, mountain view, and pool, accommodating up to 8 guests.
from $364
per night
from $364
per night
View deal
House Pittsfield
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented lovely vacation home with terrace & grill | Suitable for remote work | Dogs allowed

Pittsfield, Berkshire County, Massachusetts, United States
This family-friendly house rental in Pittsfield features a fireplace, kitchen, and parking, welcoming up to six guests and pets.
from $255
per night
Good(13 ratings)
from $255
per night
View deal
Condo Pittsfield
Condo ∙ 4 guests ∙ 1 bedroom

Family-friendly condo with garden, hot tub & BBQ | City view | Suitable for remote work | Pets allowed

Pittsfield, Berkshire County, Massachusetts, United States
This Pittsfield condo features a pool, hot tub, sauna, and mountain views, perfect for a family getaway with all amenities.
from $199
per night
from $199
per night
View deal
Apartment Pittsfield
Apartment ∙ 6 guests ∙ 3 bedrooms

Rental apartment with 3 rooms for 6 persons

Pittsfield, Berkshire County, Massachusetts, United States
from $281
per night
from $281
per night
View deal
Apartment Pittsfield
Apartment ∙ 2 guests ∙ 1 bedroom

Family-friendly rental apartment with BBQ, pool & yard | Suitable for remote work

Pittsfield, Berkshire County, Massachusetts, United States
This Pittsfield apartment rental features a pool, fireplace, kitchen, and yard, perfect for a family getaway with parking included.
from $126
per night
from $126
per night
View deal
House Pittsfield
House ∙ 7 guests ∙ 4 bedrooms

House | Suitable for remote work

Pittsfield, Berkshire County, Massachusetts, United States
This house rental in Pittsfield features a kitchen and parking, accommodating up to seven guests for an unforgettable getaway.
from $436
per night
Outstanding(2 ratings)
from $436
per night
View deal
House Pittsfield
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with terrace, garden & grill | Good for workation

Pittsfield, Berkshire County, Massachusetts, United States
This spacious house rental in Pittsfield features a private heated pool, a yard, and room for 10, perfect for family gatherings.
from $298
per night
from $298
per night
View deal
House Pittsfield
House ∙ 5 guests ∙ 2 bedrooms

Vacation home with barbeque & patio | City view | Good for workation

Pittsfield, Berkshire County, Massachusetts, United States
This house rental in Pittsfield offers a kitchen, parking, and space for five, perfect for your next family getaway.
from $160
per night
Outstanding(10 ratings)
from $160
per night
View deal
House Pittsfield
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly charming vacation home with yard, BBQ & terrace | Dogs allowed

Pittsfield, Berkshire County, Massachusetts, United States
This inviting house rental in Pittsfield features a fireplace, kitchen, balcony, and yard, perfect for a family getaway.
from $165
per night
Very good(21 ratings)
from $165
per night
View deal
House Pittsfield
House ∙ 14 guests ∙ 5 bedrooms

House with patio & grill | Lake view

Pittsfield, Berkshire County, Massachusetts, United States
This waterfront house in Pittsfield accommodates 14 guests with a kitchen, fireplace, and family-friendly amenities for an unforgettable stay.
from $1,086
per night
Outstanding(60 ratings)
from $1,086
per night
View deal
House Pittsfield
House ∙ 16 guests ∙ 6 bedrooms

Child-friendly house with barbecue, terrace & private pool | Lake view

Pittsfield, Berkshire County, Massachusetts, United States
This spacious house rental in Pittsfield boasts a private heated pool, waterfront access, and stunning mountain views for 16 guests.
from $669
per night
Outstanding(47 ratings)
from $669
per night
View deal
House Pittsfield
House ∙ 12 guests ∙ 4 bedrooms

Family-oriented house with garden, patio & barbeque | Good for workation | Pets allowed

Pittsfield, Berkshire County, Massachusetts, United States
This Pittsfield house rental for 12 features a yard, kitchen, and fireplace, perfect for a family getaway with pets.
from $458
per night
Outstanding(45 ratings)
from $458
per night
View deal
House Pittsfield
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped nice vacation home with yard, patio & barbeque | Perfect for remote work | Pet-friendly

Pittsfield, Berkshire County, Massachusetts, United States
This Pittsfield house rental features a yard, fireplace, and parking, accommodating up to eight guests and pets for a memorable stay.
from $295
per night
Excellent(18 ratings)
from $295
per night
View deal
House Pittsfield
House ∙ 9 guests ∙ 5 bedrooms

Children-friendly vacation home with garden | Good for workation | Pet-friendly

Pittsfield, Berkshire County, Massachusetts, United States
This family-friendly house rental in Pittsfield features a fireplace, yard, balcony, and ample parking for a memorable stay.
from $291
per night
Outstanding(25 ratings)
from $291
per night
View deal
Cabin Pittsfield
Cabin ∙ 5 guests ∙ 1 bedroom

Child-friendly cottage with patio, barbeque & yard | Lake view | Suitable for remote work

Pittsfield, Berkshire County, Massachusetts, United States
This Pittsfield cabin offers a waterfront view, family-friendly space, a kitchen, and parking, perfect for your next getaway.
from $160
per night
Outstanding(21 ratings)
from $160
per night
View deal

Vacation rentals and apartments with air conditioning

House Pittsfield
from $300
per night
House ∙ 9 guests ∙ 5 bedrooms

Family-friendly vacation home with garden | Mountain view | Pet-friendly

4.7
Excellent(3 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Air conditioning
View deal
House Pittsfield
from $563
per night
House ∙ 10 guests ∙ 5 bedrooms

Family-friendly vacation home with patio, barbeque & garden | Suitable for remote work

4.9
Outstanding(29 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Air conditioning
View deal
Condo Pittsfield
from $661
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Children-friendly condo with pool | Ski nearby | Suitable for remote work | Dogs allowed

Pittsfield, Berkshire County, Massachusetts, United States
Air conditioning
View deal
See all offers

Vacation Rentals With Fireplaces

Apartment Pittsfield
from $258
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Child-friendly lovely holiday apartment

Pittsfield, Berkshire County, Massachusetts, United States
Fireplace
View deal
House Pittsfield
from $400
per night
House ∙ 14 guests ∙ 5 bedrooms

Vacation home with garden, jacuzzi & patio | Lake view

4.7
Excellent(73 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Fireplace
View deal
House Pittsfield
from $338
per night
House ∙ 6 guests ∙ 3 bedrooms

House with garden & BBQ | Mountain view

4.7
Excellent(177 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Fireplace
View deal
See all offers

Vacation Rentals With Saunas

Villa Pittsfield
from $201
per night
Villa ∙ 6 guests ∙ 2 bedrooms

Villa with sauna, pool & grill

Pittsfield, Berkshire County, Massachusetts, United States
Sauna
View deal
Villa Pittsfield
from $179
per night
Villa ∙ 6 guests ∙ 2 bedrooms

Family-oriented nice villa with pool, sauna & jacuzzi

Pittsfield, Berkshire County, Massachusetts, United States
Sauna
View deal
House Pittsfield
from $581
per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with sauna, patio & pool | Mountain view

5.0
Outstanding(30 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Sauna
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Pittsfield offering exceptional value for money

Apartment Pittsfield
from $161
per night
Apartment ∙ 4 guests ∙ 1 bedroom

Holiday apartment with 1 room for 4 persons

Pittsfield, Berkshire County, Massachusetts, United States
View deal
Accommodation Pittsfield
from $131
per night
Accommodation ∙ 4 guests ∙ 1 bedroom

Fully equipped nice rental with terrace

4.3
Very good(278 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
View deal
Accommodation Pittsfield
from $125
per night
Accommodation ∙ 3 guests ∙ 1 bedroom

Fully equipped rental with terrace | Perfect for remote work | Dogs allowed

4.3
Very good(278 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
View deal

Top-Rated Vacation rentals in Pittsfield

Book the highest-rated Pittsfield vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Apartment Pittsfield
from $474
per night
Apartment ∙ 15 guests ∙ 4 bedrooms

Child-friendly holiday apartment with patio, barbeque & jacuzzi | Ski nearby | Pet-friendly

4.9
Outstanding(89 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
View deal
House Pittsfield
from $501
per night
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped pleasant house with yard & BBQ

5.0
Outstanding(70 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
View deal
House Pittsfield
from $946
per night
House ∙ 12 guests ∙ 6 bedrooms

Vacation home with private pool & barbeque

4.6
Excellent(57 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
View deal

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Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

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Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Features & Amenities in Pittsfield

  • Pet-friendly (76)
  • WiFi (192)
  • Air conditioning (189)
  • Parking (5)
  • Kitchen (74)
  • TV (171)
  • Pool (95)
  • Grill (39)
  • Washing machine (108)
  • No smoking (181)
  • Dishwasher (62)
  • Microwave (147)

Finding a vacation rental with a pool shouldn't be too difficult in Pittsfield. More than half of the accommodations offer pools. Additionally, more hotel room offer a pool than motel. Most of the hotel room with pools in Pittsfield can welcome 7 guests and have an average cost of $314 per night. Among these accommodations, 56 of them are within 2 miles of water.

Information about vacation rentals in Pittsfield

🏡 Vacation rentals available 197 rentals
🌙 Nightly prices starting at $117
⭐ Popular amenities Pets allowed, Internet and Air conditioning
🐾 Pet friendly homes 80 homes
🏊 Vacation rentals with pools 99 homes
2 reviews
Pittsfield vacation rentals have an average rating of 4/5 on 2 reviews left by travelers.

Frequently Asked Questions

What is the average price per night for a vacation rental in Pittsfield?

The price of a night's stay in Pittsfield starts at $117. Nightly prices for house rentals are $659 on average. Apartment rentals in Pittsfield cost on average $221 per night.

How many vacation rentals are available for booking in Pittsfield?

Currently there are 197 vacation rentals in Pittsfield to choose from and rent for your trip.

What amenities are most popular for vacation homes in Pittsfield?

If you're looking to book a vacation rental in Pittsfield, travelers search for accommodation with Internet, Pets allowed and Air conditioning.

How many vacation homes with a pool are there in Pittsfield?

Pittsfield has 99 Hotel room and Motel options on offer to rent.

Are dogs allowed in vacation homes in Pittsfield?

Finding a rental in Pittsfield that allows pets is definitely possible, with 80 pet-friendly available.

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