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
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Pittsfield vacation rentals

View from property

1. 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, (188 reviews)
"It was an enjoyable stay."
United States
Marybeth
The price is AED 529
AED 733 total
includes taxes & fees
16 Sep - 17 Sep
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Lake

2. 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 AED 500
AED 542 total
includes taxes & fees
8 Sep - 9 Sep
The Cottages at Harvey Lake
Interior

3. Lakefront Salmon Cottage

Lakefront Salmon Cottage
Northwood
9.8 out of 10, Exceptional, (18 reviews)
"I had a wonderful stay at the cottage. Nancy met me there and gave me a gift! The cottage was perfect! Clean and welcoming. I will definitely be back!"
United States
susan l.
The price is AED 499
AED 622 total
includes taxes & fees
8 Sep - 9 Sep
Lakefront Salmon Cottage
Dining

4. 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 AED 571
AED 707 total
includes taxes & fees
19 Aug - 20 Aug
Lakefront Yellow Cottage
Dining

5. Lakefront Pink Cottage

Lakefront Pink Cottage
Northwood
10.0 out of 10, Exceptional, (4 reviews)
"We had an enjoyable two night stay at the cabin. Our dog loved his first ever swim and we wanted to stay longer."
United States
Matty B.
The price is AED 609
AED 753 total
includes taxes & fees
19 Aug - 20 Aug
Lakefront Pink Cottage
Exterior

6. 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 AED 560
AED 695 total
includes taxes & fees
31 Aug - 1 Sep
Lakefront Purple Cottage
Sun loungers

7. Lakes Region Cozy Camp in Shellcamp

Lakes Region Cozy Camp in Shellcamp
Gilmanton
9.8 out of 10, Exceptional, (27 reviews)
"Excellent and Know host. Great view. Very clean."
United States
Jonathan
The price is AED 845
AED 1,323 total
includes taxes & fees
19 Aug - 20 Aug
Lakes Region Cozy Camp in Shellcamp
Interior

8. Lakefront Blue Cottage

Lakefront Blue Cottage
Northwood
10.0 out of 10, Exceptional, (3 reviews)
"The cabin was perfect. Quiet, comfy, and the use of the lake was great. We loved getting out on the lake with the supplied kayaks. We would definitely stay again. It wasn't fancy but great for relaxing "
United States
Geraldine M.
The price is AED 753
AED 937 total
includes taxes & fees
20 Aug - 21 Aug
Lakefront Blue Cottage
Property grounds

9. Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
Gilmanton
9.8 out of 10, Exceptional, (66 reviews)
"Great stay!"
United States
Matthew C.
The price is AED 716
AED 2,048 total
includes taxes & fees
3 Sep - 4 Sep
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
Exterior

10. Lakefront Secluded Cottage in Northwood, New Hampshire

Lakefront Secluded Cottage in Northwood, New Hampshire
Northwood
The price is AED 554
AED 688 total
includes taxes & fees
7 Sep - 8 Sep
Lakefront Secluded Cottage in Northwood, New Hampshire
Marina

11. Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi

Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi
Alton
10.0 out of 10, Exceptional, (18 reviews)
"We thoroughly enjoyed our stay at your cozy, clean, comfy cabin. It was a fun place to spend our couple of days of vacation "
United States
Jackie r.
The price is AED 496
AED 1,076 total
includes taxes & fees
8 Sep - 9 Sep
Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi
House (2 Bedrooms) | Interior

12. 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 AED 911
AED 2,085 total
includes taxes & fees
19 Aug - 20 Aug
7 Mi to Hiking: Waterfront Long Pond Gem!
Interior

13. Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!

Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Alton
10.0 out of 10, Exceptional, (1 review)
"This is a classic old-style cabin that reminded us of our childhood family trips in the 60’s. It’s not new, but a heck of a lot of fun if you’re in the right head space. Easily walked to town for dinner and to the shore. Clean and had everything we needed."
United States
Christine F.
The price is AED 422
AED 868 total
includes taxes & fees
8 Sep - 9 Sep
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Exterior

14. 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 AED 609
AED 661 total
includes taxes & fees
30 Aug - 31 Aug
Lakefront Orange Cottage
Interior

15. Lakefront Green Cottage

Lakefront Green Cottage
Northwood
10.0 out of 10, Exceptional, (6 reviews)
"Great place. "
United States
Joseph G.
The price is AED 560
AED 695 total
includes taxes & fees
30 Aug - 31 Aug
Lakefront Green Cottage
Interior

16. 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, (38 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 AED 624
AED 1,343 total
includes taxes & fees
16 Sep - 17 Sep
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
TV, fireplace, video games, foosball

17. Cozy Long Pond Winter Retreat: Waterfront Gem!

Cozy Long Pond Winter Retreat: Waterfront Gem!
Barrington
9.6 out of 10, Exceptional, (11 reviews)
"We had a lovely time! The place was beautiful, clean, and well equipped (with kayaks/life jackets, fishing gear, and games). The pond is gorgeous and has plenty of ducks, turtles and fish. "
United States
Alexander H.
The price is AED 724
AED 2,136 total
includes taxes & fees
19 Aug - 20 Aug
Cozy Long Pond Winter Retreat: Waterfront Gem!
TV

18. 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 AED 459
AED 1,364 total
includes taxes & fees
15 Sep - 16 Sep
Newly Renovated Cottage 4 in Alton Bay, NH
Private kitchen

19. 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 AED 628
AED 1,459 total
includes taxes & fees
8 Sep - 9 Sep
Cozy Cottage on a Lake, near Gunstock Mountain
TV, fireplace, books

20. 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 AED 771
AED 1,268 total
includes taxes & fees
16 Sep - 17 Sep
Farmhouse Apartment on a Highland Cattle Farm - A
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

Steele Hill Resorts

Steele Hill Resorts

10/10 Excellent
"The views were amazing! The property has everything if you feel like just staying there without traveling. Fun for everyone!"
Jodi 3-night trip
Posted 11 hours ago
Steele Hill Resorts

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

How many vacation rentals will I find in Pittsfield?

Expedia has 3 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.