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

Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Pittsfield vacation 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, (167 reviews)
"How clean the cabin is feel so peaceful over there"
United States
Jessica
The price is P9,767
P13,263 total
includes taxes & fees
Aug 3 - Aug 4
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Interior

On Baxter Lake: Wooded Retreat Near Trails

On Baxter Lake: Wooded Retreat Near Trails
3.0 star property
Farmington
The price is P11,364
P27,414 total
includes taxes & fees
Jul 8 - Jul 9
On Baxter Lake: Wooded Retreat Near Trails
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 P10,013
P10,864 total
includes taxes & fees
Jul 7 - Jul 8
The Cottages at Harvey Lake
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 P19,018
P29,632 total
includes taxes & fees
Jul 7 - Jul 8
9 Lake Street
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 P15,234
P34,874 total
includes taxes & fees
Jul 17 - Jul 18
7 Mi to Hiking: Waterfront Long Pond Gem!
Interior

2 Mi to Winnipesaukee Shores: Gunstock Retreat

2 Mi to Winnipesaukee Shores: Gunstock Retreat
3.0 star property
Gilford
The price is P31,697
P58,850 total
includes taxes & fees
Jul 16 - Jul 17
2 Mi to Winnipesaukee Shores: Gunstock Retreat
Interior

Hiking & Snowmobile Trails On-site: Alton Retreat!

Hiking & Snowmobile Trails On-site: Alton Retreat!
3.0 star property
Alton
Hiking & Snowmobile Trails On-site: Alton Retreat!
Interior

Quiet New Hampshire Getaway w/ Game Room!

Quiet New Hampshire Getaway w/ Game Room!
3.0 star property
Locke Lake Colony
Quiet New Hampshire Getaway w/ Game Room!
Interior

Lake Getaway: Walk Across Street to Private Beach!

Lake Getaway: Walk Across Street to Private Beach!
3.0 star property
Gilford
6.0 out of 10, (1 review)
The price is P8,846
P16,038 total
includes taxes & fees
Jul 26 - Jul 27
Lake Getaway: Walk Across Street to Private Beach!
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.
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Top Pittsfield Hotel Reviews

The Lake Estate on Winnisquam

The Lake Estate on Winnisquam

10/10 Excellent
"The room was huge. We really enjoyed how nicely furnished the hotel. The lake was a lot of fun."
Jennifer 1-night trip
Posted 1 hour ago
The Lake Estate on Winnisquam

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:

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

Frequently asked questions

Can I find vacation rentals in Pittsfield?

Yes, there are vacation rentals close to popular local attractions in Pittsfield, or you can select a secluded option if you'd like a relaxing place to stay.

How many vacation rentals will I find in Pittsfield?

Expedia has 4 vacation 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 vacation rental in Pittsfield like?

Vacation rentals are private properties you can stay in for short or long periods in Pittsfield. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.