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

Vacation rentals in Pittsfield

Browse 190 available vacation homes and compared across 6 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+

  • Popular amenities

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

  • Other Services

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

House Pittsfield
House ∙ 10 guests ∙ 5 bedrooms

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

Pittsfield, Berkshire County, Massachusetts, United States
This Pittsfield house rental features a kitchen, fireplace, and yard, perfect for families seeking an unforgettable getaway.
from $533
per night
Outstanding(29 ratings)
from $533
per night
View deal
House Pittsfield
House ∙ 10 guests ∙ 3 bedrooms

Children-friendly wonderful vacation home with barbeque & patio | Lake 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 $356
per night
Outstanding(98 ratings)
from $356
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 $146
per night
Outstanding(23 ratings)
from $146
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 $588
per night
Outstanding(25 ratings)
from $588
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 $492
per night
Outstanding(60 ratings)
from $492
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 $292
per night
Excellent(19 ratings)
from $292
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 $221
per night
Outstanding(59 ratings)
from $221
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 $280
per night
Outstanding(102 ratings)
from $280
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 $419
per night
Outstanding(40 ratings)
from $419
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 $663
per night
Outstanding(100 ratings)
from $663
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 $897
per night
Outstanding(47 ratings)
from $897
per night
View deal
House Pittsfield
House ∙ 14 guests ∙ 6 bedrooms

Family-oriented big vacation home with terrace, garden & private pool | Perfect for remote work

Pittsfield, Berkshire County, Massachusetts, United States
This Pittsfield house rental features a private heated pool, hot tub, sauna, and spacious yard, perfect for family gatherings.
from $1,405
per night
Outstanding(17 ratings)
from $1,405
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 $316
per night
Outstanding(10 ratings)
from $316
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 $123
per night
Outstanding(10 ratings)
from $123
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 $330
per night
Very good(15 ratings)
from $330
per night
View deal

Vacation rentals with a balcony

Cabin Pittsfield
from $426
per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with grill, patio & yard | Perfect for remote work

5.0
Outstanding(28 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Balcony
View deal
House Pittsfield
from $394
per night
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented ample vacation home with yard, patio & BBQ | Nature view | Suitable for remote work | Pet-friendly

5.0
Outstanding(110 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Balcony
View deal
House Pittsfield
from $565
per night
House ∙ 5 guests ∙ 3 bedrooms

Vacation home with barbeque & terrace | Perfect for remote work

5.0
Outstanding(37 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Balcony
View deal
See all offers

Vacation Homes With Fishing Spots Nearby

House Pittsfield
from $281
per night
House ∙ 8 guests ∙ 4 bedrooms

House with terrace & grill

4.9
Outstanding(11 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Fishing
View deal
House Pittsfield
from $273
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with patio, barbecue & garden | Nature view

5.0
Outstanding(34 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Fishing
View deal
House Pittsfield
from $449
per night
House ∙ 8 guests ∙ 5 bedrooms

Fully equipped vacation home with terrace & barbeque | Lake view

4.9
Outstanding(14 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Fishing
View deal
See all offers

Vacation Rentals With Saunas

Villa Pittsfield
from $192
per night
Villa ∙ 6 guests ∙ 2 bedrooms

Family-oriented nice villa with pool, sauna & jacuzzi

Pittsfield, Berkshire County, Massachusetts, United States
Sauna
View deal
Villa Pittsfield
from $134
per night
Villa ∙ 4 guests ∙ 1 bedroom

Villa with sauna, jacuzzi & BBQ

Pittsfield, Berkshire County, Massachusetts, United States
Sauna
View deal
Villa Pittsfield
from $233
per night
Villa ∙ 8 guests ∙ 3 bedrooms

Villa with BBQ, sauna & hot tub

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

House Pittsfield
from $208
per night
House ∙ 4 guests ∙ 1 bedroom

Fully equipped vacation home with yard | Good for workation

Pittsfield, Berkshire County, Massachusetts, United States
View deal
Accommodation Pittsfield
from $141
per night
Accommodation ∙ 4 guests ∙ 1 bedroom

Rental with garden & patio | Garden view

4.3
Very good(379 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
View deal
Apartment Pittsfield
from $162
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Charming holiday apartment with 1 bedroom for 2 persons

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 $1,149
per night
House ∙ 20 guests ∙ 6 bedrooms

Child-friendly vacation home with garden, barbeque & terrace | Nature view | Perfect for remote work

5.0
Outstanding(287 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
View deal
House Pittsfield
from $223
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented pleasant vacation home with barbecue, terrace & yard | Mountain view | Suitable for remote work

5.0
Outstanding(107 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
View deal
House Pittsfield
from $902
per night
House ∙ 12 guests ∙ 6 bedrooms

Vacation home with private pool, hot tub & barbeque

4.6
Excellent(61 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
View deal

Why choose HomeToGo?

Securely pay and stay your way

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Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Award-winning customer service

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.

Price clarity, no surprises

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 7 guests and have an average cost of $331 per night. Among these accommodations, 59 of them are within 2 miles of water.

Information about vacation rentals in Pittsfield

🏡 Vacation rentals available 190 rentals
🌙 Nightly prices starting at $113
⭐ Popular amenities Pets allowed, Internet and Air conditioning
🐾 Pet friendly homes 96 homes
🏊 Vacation rentals with pools 94 homes

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 $113. Nightly prices for house rentals are $705 on average. Apartment rentals in Pittsfield cost on average $215 per night.

How many vacation rentals are available for booking in Pittsfield?

Currently there are 190 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 94 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 96 pet-friendly available.

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