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

Vacation rentals in Pittsfield

Browse 193 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

    • 2 mi
    • 3 mi
    • Any

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • 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 193 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Pittsfield
House ∙ 9 guests ∙ 5 bedrooms

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

Pittsfield, Berkshire County, Massachusetts, United States
This spacious house rental in Pittsfield features a mountain view, fireplace, kitchen, balcony, and a yard perfect for families and pets.
from $301
per night
Excellent(3 ratings)
from $301
per night
View deal
House Pittsfield
House ∙ 4 guests ∙ 2 bedrooms

Family-oriented lovely house with garden, terrace & barbeque | Mountain view | Pets are welcome

Pittsfield, Berkshire County, Massachusetts, United States
This house rental in Pittsfield features a yard, mountain view, and a fireplace, making it perfect for a family getaway with pets.
from $301
per night
Outstanding(103 ratings)
from $301
per night
View deal
House Pittsfield
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with yard, grill & patio | Mountain view

Pittsfield, Berkshire County, Massachusetts, United States
This waterfront house in Pittsfield features a balcony, fireplace, and yard, perfect for family gatherings with stunning mountain views.
from $674
per night
Outstanding(82 ratings)
from $674
per night
View deal
House Pittsfield
House ∙ 28 guests ∙ 8 bedrooms

Vacation home with hot tub, patio & garden | Lake view | Good for workation

Pittsfield, Berkshire County, Massachusetts, United States
This waterfront house rental in Pittsfield features a hot tub, mountain views, and ample space for 28 guests, perfect for families.
from $276
per night
Outstanding(168 ratings)
from $276
per night
View deal
House Pittsfield
House ∙ 10 guests ∙ 4 bedrooms

House with terrace, barbecue & hot tub | Lake view

Pittsfield, Berkshire County, Massachusetts, United States
This waterfront house in Pittsfield features a hot tub, fireplace, and balcony, accommodating up to 10 guests for a memorable stay.
from $447
per night
Outstanding(14 ratings)
from $447
per night
View deal
House Pittsfield
House ∙ 10 guests ∙ 3 bedrooms

Children-friendly wonderful vacation home with barbeque & patio | Nature view

Pittsfield, Berkshire County, Massachusetts, United States
This waterfront house rental in Pittsfield offers a kitchen, fireplace, and parking, perfect for family gatherings of up to 10.
from $401
per night
Outstanding(95 ratings)
from $401
per night
View deal
House Pittsfield
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped house with yard, patio & barbeque | Mountain view | Suitable for remote work

Pittsfield, Berkshire County, Massachusetts, United States
This house rental in Pittsfield features a fireplace, kitchen, yard, mountain view, and parking, accommodating up to 8 guests.
from $369
per night
Outstanding(39 ratings)
from $369
per night
View deal
House Pittsfield
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with terrace, garden & barbecue | Lake view

Pittsfield, Berkshire County, Massachusetts, United States
This waterfront house in Pittsfield features a balcony, kitchen, and yard, perfect for family gatherings of up to 10.
from $776
per night
Outstanding(98 ratings)
from $776
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 $155
per night
Very good(21 ratings)
from $155
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 $489
per night
Outstanding(45 ratings)
from $489
per night
View deal
House Pittsfield
House ∙ 10 guests ∙ 5 bedrooms

House with barbecue, patio & yard | Perfect for remote work

Pittsfield, Berkshire County, Massachusetts, United States
This house rental in Pittsfield features a hot tub, fireplace, and a spacious yard, perfect for family gatherings and pets.
from $477
per night
Outstanding(21 ratings)
from $477
per night
View deal
House Pittsfield
House ∙ 7 guests ∙ 4 bedrooms

Family-oriented charming house with barbeque & yard

Pittsfield, Berkshire County, Massachusetts, United States
This house rental in Pittsfield features a fireplace, kitchen, balcony, and yard, perfect for family gatherings with parking.
from $374
per night
Outstanding(3 ratings)
from $374
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 $310
per night
Excellent(15 ratings)
from $310
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 $560
per night
Outstanding(58 ratings)
from $560
per night
View deal
House Pittsfield
House ∙ 6 guests ∙ 3 bedrooms

House with yard & grill | Mountain view | Ski nearby | Pet-friendly

Pittsfield, Berkshire County, Massachusetts, United States
This house rental in Pittsfield features a kitchen, yard, mountain view, and parking, accommodating up to six guests and pets.
from $199
per night
Outstanding(61 ratings)
from $199
per night
View deal

Vacation rentals and apartments with air conditioning

House Pittsfield
from $344
per night
House ∙ 9 guests ∙ 5 bedrooms

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

4.9
Outstanding(26 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Air conditioning
View deal
House Pittsfield
from $642
per night
House ∙ 10 guests ∙ 5 bedrooms

Fully equipped beautiful house with BBQ & yard

5.0
Outstanding(2 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Air conditioning
View deal
Accommodation Pittsfield
from $125
per night
Accommodation ∙ 4 guests ∙ 1 bedroom

Rental with garden & patio | Garden view

4.3
Very good(278 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Air conditioning
View deal
See all offers

Vacation Rentals With Saunas

Villa Pittsfield
from $158
per night
Villa ∙ 6 guests ∙ 2 bedrooms

Family-oriented nice villa with pool, sauna & jacuzzi

Pittsfield, Berkshire County, Massachusetts, United States
Sauna
View deal
Apartment Pittsfield
from $263
per night
Apartment ∙ 8 guests ∙ 2 bedrooms

Rental apartment with jacuzzi, sauna & pool | Mountain view

5.0
Outstanding(41 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Sauna
View deal
House Pittsfield
from $569
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

Vacation rentals with Wi-Fi

Apartment Pittsfield
from $148
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Fully equipped lovely holiday apartment

Pittsfield, Berkshire County, Massachusetts, United States
Internet
View deal
House Pittsfield
from $251
per night
House ∙ 8 guests ∙ 3 bedrooms

Wonderful house with barbecue

Pittsfield, Berkshire County, Massachusetts, United States
Internet
View deal
Lodge Pittsfield
from $134
per night
Lodge ∙ 3 guests ∙ 1 bedroom

Fully equipped nice lodge with pool & BBQ | Suitable for remote work

4.4
Very good(474 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Internet
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Pittsfield offering exceptional value for money

House Pittsfield
from $532
per night
House ∙ 10 guests ∙ 5 bedrooms

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

5.0
Outstanding(63 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
View deal
Accommodation Pittsfield
from $99
per night
Accommodation ∙ 3 guests ∙ 1 bedroom

Fully equipped rental with terrace

4.3
Very good(278 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
View deal
House Pittsfield
from $1,009
per night
House ∙ 14 guests ∙ 6 bedrooms

Family-friendly house with hot tub, yard & sauna | Mountain view

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

House Pittsfield
from $330
per night
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly lovely house with patio & BBQ | Pets are welcome

5.0
Outstanding(254 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
View deal
House Pittsfield
from $524
per night
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped vacation home with yard, terrace & grill

5.0
Outstanding(87 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
View deal
House Pittsfield
from $526
per night
House ∙ 14 guests ∙ 5 bedrooms

Vacation home with garden, jacuzzi & patio | Lake view

4.6
Excellent(72 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. Nearly 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 4 guests and have an average cost of $257 per night. Among these accommodations, 58 of them are within 2 miles of water.

Information about vacation rentals in Pittsfield

🏡 Vacation rentals available 193 rentals
🌙 Nightly prices starting at $82
⭐ Popular amenities Pets allowed, Internet and Air conditioning
🐾 Pet friendly homes 76 homes
🏊 Vacation rentals with pools 95 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 $82. Nightly prices for house rentals are $654 on average. Apartment rentals in Pittsfield cost on average $185 per night.

How many vacation rentals are available for booking in Pittsfield?

Currently there are 193 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 95 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 76 pet-friendly available.

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