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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (221 reviews)
"Great stay"
United States
Anthony
The price is AED 496
AED 697 total
includes taxes & fees
2 Nov - 3 Nov
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
A spacious kitchen with a large island, white cabinetry, and a view of a playground through large windows.

2. Newly Renovated Cottage 3 on Main Street Alton Bay!

Newly Renovated Cottage 3 on Main Street Alton Bay!
Alton
9.6 out of 10, Exceptional, (7 reviews)
"Staff was very freindly"
United States
David
The price is AED 426
AED 864 total
includes taxes & fees
29 Oct - 30 Oct
Newly Renovated Cottage 3 on Main Street Alton Bay!
A coastal town with a marina, a large cruise ship docked, and a beach.

3. Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3

Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3
Alton
8.8 out of 10, Excellent, (14 reviews)
"Nicely kept enjoyable stay"
United States
Shirley G.
Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3
A cozy room with a wicker sofa, a wooden ladder shelf, and a large wooden-framed window.

4. 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 430
AED 1,320 total
includes taxes & fees
27 Oct - 28 Oct
Newly Renovated Cottage 4 in Alton Bay, NH
A cabin with a deck, surrounded by trees and a small body of water.

5. Modern & Cozy Lakefront Cabin: Rustic Charm and Serene views

Modern & Cozy Lakefront Cabin: Rustic Charm and Serene views
Barnstead
9.4 out of 10, Exceptional, (18 reviews)
"The cabin was very cozy and the view of the lake was beautiful to wake up to every morning. "
United States
Jessica C.
The price is AED 1,245
AED 2,455 total
includes taxes & fees
25 Oct - 26 Oct
Modern & Cozy Lakefront Cabin: Rustic Charm and Serene views
A modern living room with a grey sofa, a floor lamp, and a hanging plant.

6. New, Clean, Downtown Getaway!

New, Clean, Downtown Getaway!
Concord
9.0 out of 10, Wonderful, (11 reviews)
"Quiet location with great walkable small town feel!"
United States
Kerry L.
The price is AED 458
AED 696 total
includes taxes & fees
4 Oct - 5 Oct
New, Clean, Downtown Getaway!
A wooden cabin interior with a dining table, chairs, a sofa, and a TV.

7. A - Farmhouse Apartment on a Cattle Farm

A - Farmhouse Apartment on a Cattle Farm
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 802
AED 1,305 total
includes taxes & fees
22 Oct - 23 Oct
A - Farmhouse Apartment on a Cattle Farm
A modern interior with a large sliding glass door leading to an outdoor deck.

8. Cozy Long Pond Winter Retreat: Waterfront Gem!

Cozy Long Pond Winter Retreat: Waterfront Gem!
Barrington
9.6 out of 10, Exceptional, (13 reviews)
"Very nice location on the lake was very pleased on everything that was offered it had canoes paddle boards fishing poles and a bunch more than what was expected and will definitely use this place again for my next trip"
United States
David S G.
The price is AED 724
AED 2,108 total
includes taxes & fees
9 Oct - 10 Oct
Cozy Long Pond Winter Retreat: Waterfront Gem!
A bedroom with a bed, bedside tables, a wardrobe, and a kitchen area.

9. Picturesque Studio Lakefront - Dock

Picturesque Studio Lakefront - Dock
Alton
The price is AED 606
AED 1,370 total
includes taxes & fees
6 Oct - 7 Oct
Picturesque Studio Lakefront - Dock
A narrow kitchen with a stove, white cabinets, and a wooden floor.

10. Cozy Cottage on a Lake, near Gunstock Mountain

Cozy Cottage on a Lake, near Gunstock Mountain
Gilmanton
9.0 out of 10, Wonderful, (8 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 1,463 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Cottage on a Lake, near Gunstock Mountain
A wooden cabin interior with a dining table set for four, surrounded by wooden chairs.

11. On Baxter Lake: Wooded Retreat Near Trails

On Baxter Lake: Wooded Retreat Near Trails
Farmington
10.0 out of 10, Exceptional, (5 reviews)
"What a beautiful and cozy little property! We really enjoyed our stay."
United States
Rebekah
The price is AED 566
AED 1,718 total
includes taxes & fees
5 Oct - 6 Oct
On Baxter Lake: Wooded Retreat Near Trails
A cozy cabin interior with a sectional sofa, a leather ottoman, and a television mounted on the wall.

12. Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...

Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
Alton
10.0 out of 10, Exceptional, (5 reviews)
"Best communication ever at a VRBO. When I come back, I’m there!"
United States
shaun d.
The price is AED 680
AED 1,518 total
includes taxes & fees
4 Oct - 5 Oct
Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
A cozy room with a hammock, wicker furniture, and a view of a lush garden.

13. 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, (45 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 823
AED 1,571 total
includes taxes & fees
12 Oct - 13 Oct
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
A modern kitchen with white cabinets, a microwave, and a stove.

14. 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 430
AED 868 total
includes taxes & fees
18 Oct - 19 Oct
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
A cozy room with a large window, a sofa, a coffee table, and a wicker chair.

15. Locke Lake House

Locke Lake House
Barnstead
10.0 out of 10, Exceptional, (1 review)
"Perfect for our littles, the house is right on the water. Great location, clean house. We told the host we had trouble with AC they came over to install another window unit. My daughter got sick and they answered the phone immediately to suggest a local urgent care. Very responsible, respectful of our privacy and a lovely house. We would stay again."
United States
Jennifer L.
The price is AED 1,349
AED 3,052 total
includes taxes & fees
1 Nov - 2 Nov
Locke Lake House
A modern living room with a grey sofa, a coffee table, and large windows offering a view of the outside.

16. Charming Alton Bay Getaway – 1BR Cottage, Pool Access & Walk to Lake

Charming Alton Bay Getaway – 1BR Cottage, Pool Access & Walk to Lake
Alton
9.0 out of 10, Wonderful, (2 reviews)
The price is AED 452
AED 900 total
includes taxes & fees
22 Oct - 23 Oct
Charming Alton Bay Getaway – 1BR Cottage, Pool Access & Walk to Lake
A modern interior with a large sliding glass door leading to an outdoor deck.

17. 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
9 Oct - 10 Oct
7 Mi to Hiking: Waterfront Long Pond Gem!
A beach with clear water, a sandy shore, and a few trees in the background.

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

Fantastic Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi
Alton
9.0 out of 10, Wonderful, (19 reviews)
"Cute cabin. Nice location!"
United States
Evan C.
The price is AED 408
AED 732 total
includes taxes & fees
7 Oct - 8 Oct
Fantastic Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi
A modern kitchen with a large island, dark cabinetry, and a view of the outdoors.

19. Stay in Venice our Modern Steps from the Lake with Dock!

Stay in Venice our Modern Steps from the Lake with Dock!
Alton
10.0 out of 10, Exceptional, (9 reviews)
"Great location on the lake!"
United States
Stephanie H.
The price is AED 602
AED 1,312 total
includes taxes & fees
9 Oct - 10 Oct
Stay in Venice our Modern Steps from the Lake with Dock!
A residential property with a wooden deck, a small garden, and a blue house with a chimney.

20. Newly Renovated Cottage on Main Street Alton Bay #5

Newly Renovated Cottage on Main Street Alton Bay #5
Alton
8.4 out of 10, Very good, (6 reviews)
"Great places. Quiet and quaint and close to the lake and restaurants. Will rent again "
United States
Brian B.
The price is AED 496
AED 972 total
includes taxes & fees
1 Nov - 2 Nov
Newly Renovated Cottage on Main Street Alton Bay #5
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

Winnisquam Lake Inn

Winnisquam Lake Inn

10/10 Excellent
"Great service"
Martin 1-night trip
Posted 1 hour ago
Winnisquam Lake Inn

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?

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski: This vacation home rental outside of Pittsfield is located on a lake and has an indoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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?

Lily Lake and Suncook River 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.