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

Pittsfield Holiday Rentals

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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!
Interior

Lakefront Salmon Cottage

Lakefront Salmon Cottage
Northwood
9.8 out of 10, Exceptional, (16 reviews)
"Awesome place for quite getaway."
United States
Jason L.
The price is HK$1,300
HK$1,615 total
includes taxes & fees
6 Aug - 7 Aug
Lakefront Salmon Cottage
Beach

Quiet New Hampshire Getaway w/ Game Room!

Quiet New Hampshire Getaway w/ Game Room!
Locke Lake Colony
10.0 out of 10, Exceptional, (11 reviews)
"I was quite satisfied with the cleanliness and the place was beautiful .It is situated near a lake and I am hoping to be back in the summer."
United States
Karen B.
The price is HK$1,678
HK$5,462 total
includes taxes & fees
6 Aug - 7 Aug
Quiet New Hampshire Getaway w/ Game Room!
Dining

Lakefront Yellow Cottage

Lakefront Yellow Cottage
Northwood
9.4 out of 10, Exceptional, (6 reviews)
"Clean, friendly, a great place to stay. I kayaked in the lake and it was beautiful. Hope to stay again next summer!"
United States
Ravaioli N.
The price is HK$1,300
HK$1,615 total
includes taxes & fees
30 Jul - 31 Jul
Lakefront Yellow Cottage
Sun-loungers

Lakes Region Cozy Camp in Shellcamp

Lakes Region Cozy Camp in Shellcamp
Gilmanton
9.8 out of 10, Exceptional, (26 reviews)
"Excellent and Know host. Great view. Very clean."
United States
Jonathan
The price is HK$1,803
HK$2,824 total
includes taxes & fees
5 Aug - 6 Aug
Lakes Region Cozy Camp in Shellcamp
Dining

Hiking & Snowmobile Trails On-Site: Alton Retreat!

Hiking & Snowmobile Trails On-Site: Alton Retreat!
Alton
10.0 out of 10, Exceptional, (6 reviews)
"Such a cute place! Great amenities! Very cozy! Would definitely stay again! "
United States
Karolyn W.
The price is HK$964
HK$2,220 total
includes taxes & fees
2 Aug - 3 Aug
Hiking & Snowmobile Trails On-Site: Alton Retreat!
Exterior

Lakefront Purple Cottage

Lakefront Purple Cottage
Northwood
9.2 out of 10, Wonderful, (7 reviews)
"Quaint colorful just right ."
United States
Susan B.
The price is HK$1,308
HK$1,624 total
includes taxes & fees
11 Aug - 12 Aug
Lakefront Purple Cottage
Interior

Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit

Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Gilmanton
9.8 out of 10, Exceptional, (37 reviews)
"Lovely stay in a quiet area. The hot tub was great to unwind in after hiking in the area!"
United States
Cristofer V.
The price is HK$2,109
HK$3,828 total
includes taxes & fees
13 Aug - 14 Aug
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Smart TV, fireplace, DVD player, books

4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock

4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock
Gilmanton
10.0 out of 10, Exceptional, (4 reviews)
"This property was immaculate and even more beautiful than the photos. The kitchen was well appointed and had everything needed to prepare meals for 8 adults for a week. The host was very responsive and helpful. I highly recommend staying here."
United States
Melanie S.
The price is HK$5,136
HK$9,044 total
includes taxes & fees
2 Aug - 3 Aug
4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock
Property grounds

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
Gilmanton
10.0 out of 10, Exceptional, (62 reviews)
"Great place! "
United States
Taylor B.
The price is HK$784
HK$3,412 total
includes taxes & fees
26 Aug - 27 Aug
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
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!
TV, fireplace, books

Farmhouse Apartment on a Highland Cattle Farm - A

Farmhouse Apartment on a Highland Cattle Farm - A
Loudon
10.0 out of 10, Exceptional, (5 reviews)
"We loved our stay the house had everything we needed. Seeing all the farm animals was amazing. We would love to come back for a longer stay. "
United States
kimberly S.
The price is HK$1,655
HK$2,715 total
includes taxes & fees
30 Jul - 31 Jul
Farmhouse Apartment on a Highland Cattle Farm - A
TV

Newly Renovated Cottage 7 in Alton Bay

Newly Renovated Cottage 7 in Alton Bay
Alton
10.0 out of 10, Exceptional, (2 reviews)
"Host was responsive and the property was just close enough to enjoy laconia without a huge price premium. Its a simple cabin, but it did what we needed it to do. Gravel parking lot is not the best for motorcycles if i had to leave constructive feedback. Would rent again."
United States
fred j.
The price is HK$2,384
HK$3,690 total
includes taxes & fees
25 Aug - 26 Aug
Newly Renovated Cottage 7 in Alton Bay
Outdoor dining

Cozy cottage get-away at Lake Winnipesaukee with swim access off dock

Cozy cottage get-away at Lake Winnipesaukee with swim access off dock
Alton
9.6 out of 10, Exceptional, (17 reviews)
"Cabin is in a great location, very quiet, very comfortable, with great features. Would definitely return again when I'm in the area."
United States
Barry
The price is HK$1,969
HK$3,370 total
includes taxes & fees
2 Aug - 3 Aug
Cozy cottage get-away at Lake Winnipesaukee with swim access off dock
Beach

The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV

The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV
Alton
9.6 out of 10, Exceptional, (17 reviews)
"Great place loved the bikes and campfire area"
United States
Desiree S.
The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV
Exterior

Lakefront Orange Cottage

Lakefront Orange Cottage
Northwood
9.0 out of 10, Wonderful, (12 reviews)
"The personal touch and welcome gift was lovely z"
United States
Joyce
The price is HK$1,365
HK$1,481 total
includes taxes & fees
9 Aug - 10 Aug
Lakefront Orange Cottage
Private kitchen

Cozy Cottage on a Lake, near Gunstock Mountain

Cozy Cottage on a Lake, near Gunstock Mountain
Gilmanton
8.8 out of 10, Excellent, (5 reviews)
"We had a wonderful time during our stay. The cottage was in a great location, exactly as advertised, and spotlessly clean. The hot tub was great. Can’t think of a single thing we’d change. Would love to come back again during the summer months."
United States
Dawn P.
The price is HK$1,341
HK$3,105 total
includes taxes & fees
12 Aug - 13 Aug
Cozy Cottage on a Lake, near Gunstock Mountain
TV

Newly Renovated Cottage 4 in Alton Bay, NH

Newly Renovated Cottage 4 in Alton Bay, NH
Alton
9.0 out of 10, Wonderful, (4 reviews)
"Communication was amazing, check in was a delightful, the house itself was perfect "
United States
Jennifer S.
The price is HK$1,505
HK$3,545 total
includes taxes & fees
25 Aug - 26 Aug
Newly Renovated Cottage 4 in Alton Bay, NH
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

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 2 hours 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
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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 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.