Lake Autumn Foliage fog

Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

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
2.0 star property
Epsom
9.6 out of 10, Exceptional, (160 reviews)
"Great stay "
United States
Edward
The price is ￥25,478
￥34,599 total
includes taxes & fees
Jun 15 - Jun 16
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
House (2 Bedrooms) | Interior

On Baxter Lake: Wooded Retreat Near Trails

On Baxter Lake: Wooded Retreat Near Trails
3.0 star property
Farmington
The price is ￥25,158
￥71,054 total
includes taxes & fees
Jun 21 - Jun 22
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, (46 reviews)
"The view of the lake from the cabin was excellent. "
United States
Matt
The price is ￥26,600
￥28,861 total
includes taxes & fees
Jul 1 - Jul 2
The Cottages at Harvey Lake
House (2 Bedrooms) | 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 ￥35,253
￥90,513 total
includes taxes & fees
Jun 14 - Jun 15
7 Mi to Hiking: Waterfront Long Pond Gem!
House (4 Bedrooms) | 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 ￥38,297
￥108,703 total
includes taxes & fees
Jun 28 - Jun 29
Quiet New Hampshire Getaway w/ Game Room!
Apartment (1 Bedroom) | 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 ￥18,588
￥41,379 total
includes taxes & fees
Jul 12 - Jul 13
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

Homewood Suites by Hilton Dover

Homewood Suites by Hilton Dover

10/10 Excellent
"I have stayed at this hotel 3 times now because how much I like it. They just changed the thermostat in the room and I couldn’t figure out how to adjust it. Otherwise very comfortable and clean."
Linda 7-night trip
Posted 1 hour ago
Homewood Suites by Hilton Dover

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
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  • 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 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.

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

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock: This vacation home rental outside of Pittsfield is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

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.