A calm lake reflecting colorful autumn trees and misty mountains in the distance.

Pittsfield Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Pittsfield holiday rentals

View from property

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
2.5 star property
Epsom
9.6 out of 10, Exceptional, (177 reviews)
"What a great experience, everyone was so kind and the room was clean and comfortable with the staff"
United States
Katherin
The price is HK$1,325
HK$1,778 total
includes taxes & fees
6 Aug - 7 Aug
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Lake

The Cottages at Harvey Lake

The Cottages at Harvey Lake
3.0 star property
Northwood
8.8 out of 10, Excellent, (47 reviews)
"The view of the lake from the cabin was excellent. "
United States
Matt
The price is HK$1,192
HK$1,293 total
includes taxes & fees
10 Aug - 11 Aug
The Cottages at Harvey Lake
Interior

Quiet New Hampshire Getaway w/ Game Room!

Quiet New Hampshire Getaway w/ Game Room!
3.0 star property
Locke Lake Colony
The price is HK$2,094
HK$5,342 total
includes taxes & fees
6 Aug - 7 Aug
Quiet New Hampshire Getaway w/ Game Room!
Private kitchen

9 Lake Street

9 Lake Street
3.0 star property
Wolfeboro
10.0 out of 10, Exceptional, (1 review)
"Great location and wonderful space! Will definitely stay again"
United States
Roog
The price is HK$2,515
HK$4,034 total
includes taxes & fees
12 Aug - 13 Aug
9 Lake Street
Interior

Hiking & Snowmobile Trails On-site: Alton Retreat!

Hiking & Snowmobile Trails On-site: Alton Retreat!
3.0 star property
Alton
The price is HK$1,294
HK$2,184 total
includes taxes & fees
2 Aug - 3 Aug
Hiking & Snowmobile Trails On-site: Alton Retreat!
Interior

7 Mi to Hiking: Waterfront Long Pond Gem!

7 Mi to Hiking: Waterfront Long Pond Gem!
3.0 star property
Barrington
10.0 out of 10, Exceptional, (1 review)
"Well designed and maintained property. We enjoyed the little touches like the automatic nightlights and heater in bathroom. Wish we could have spent more time here but we attended the Deerfield fair. Highly recommended. "
United States
Ronald
The price is HK$1,945
HK$4,451 total
includes taxes & fees
30 Jul - 31 Jul
7 Mi to Hiking: Waterfront Long Pond Gem!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Comfort Inn Concord South End

Comfort Inn Concord South End

10/10 Excellent
"Staff very polite and helpful with any questions asked. Parking is easy. Even though they provided breakfast, I went out to eat with family members."
Ramona 5-night trip
Posted 1 hour ago
Comfort Inn Concord South End

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

  • View our selection of featured holiday rentals in Pittsfield
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

Look no further and take a look at our great range of rental properties in Pittsfield!

Frequently asked questions

Can I find holiday rentals in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pittsfield has to offer?

🌟 Lakefront Bliss Awaits – Your Ultimate Getaway! 🏡🌊⛰️: This holiday home rental outside of Pittsfield is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals will I find in Pittsfield?

Expedia has 3 holiday rentals for your stay in Pittsfield.

What’s there to see and do in Pittsfield?

Suncook River and Lily Lake are a couple of scenic spots to enjoy the outdoors, whereas Scenic Theatre is one of the cultural attractions. Other places in town to visit include Josiah Carpenter Library and Pittsfield Town Hall.

What’s a holiday rental in Pittsfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pittsfield. Holiday rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a small group gathering.