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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Pittsfield vacation rentals

Northerly View from the Balcony

1. The Barn - Lake View and Pet Friendly

The Barn - Lake View and Pet Friendly
Pittsfield
6.0 out of 10, (1 review)
"It was peaceful and quiet, nice water view from the picture window , whole place was nice sized, Nice sized kitchen downstairs and office room, The main bathroom upstairs was nice and balcony was very nice, However the strong smell of animal urin all upstairs in the living room/bedroom was overwhelming, We brought our own lysol wipes to wipe everything down and used our Febreeze air spray to try to clean the smell upstairs , the little sofa looked stained and smelled, We sprayed it with...
United States
Joseph G.
The price is SAR 591
SAR 731 total
includes taxes & fees
20 Oct - 21 Oct
The Barn - Lake View and Pet Friendly
View from property

2. 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, (228 reviews)
"Great stay"
United States
Anthony
The price is SAR 477
SAR 680 total
includes taxes & fees
16 Nov - 17 Nov
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
A wooden cabin interior with a dining table, chairs, a kitchen area with cabinets, and a door with a window.

3. Hiking & Snowmobile Trails On-Site: Alton Retreat!

Hiking & Snowmobile Trails On-Site: Alton Retreat!
Alton
10.0 out of 10, Exceptional, (9 reviews)
"Perfect little spot. Clean, comfy everything you need and then some. Thanks for hosting us."
United States
Matthew M.
Hiking & Snowmobile Trails On-Site: Alton Retreat!
A wooden cabin interior with a dining table, chairs, a kitchen area with cabinets, and a door with a window.

4. 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!
An outdoor grill area with a red grill, a stainless steel grill, and a charcoal grill, surrounded by a fence and trees.

5. 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 SAR 499
SAR 961 total
includes taxes & fees
28 Oct - 29 Oct
Newly Renovated Cottage 3 on Main Street Alton Bay!
Interior

6. Stone Haven "Tent Cabin" with a cast iron fire pit in Canterbury, NH.

Stone Haven "Tent Cabin" with a cast iron fire pit in Canterbury, NH.
Canterbury
10.0 out of 10, Exceptional, (1 review)
"A beautiful little slice of heaven! I was able to give my 3 year old her first "camping" experience in a safe and cozy location. The host was awesome and very helpful and accommodating. 10/10 wouls absolutely go back"
United States
Amanda M.
The price is SAR 563
SAR 700 total
includes taxes & fees
20 Oct - 21 Oct
Stone Haven "Tent Cabin" with a cast iron fire pit in Canterbury, NH.
Rustic kitchen with charming details and modern essentials.

7. Farm Adventure | Animals + Fire Pit | Lakes Region

Farm Adventure | Animals + Fire Pit | Lakes Region
Gilmanton
8.0 out of 10, Very good, (2 reviews)
"We really enjoyed our stay in the working farm apt. The spa bathroom was spacious and beautiful, the kitchen cozy and the farm animals were so chill and sweet. The king size bed was comfortable. Communication w Patti was almost immediate. The farm workers were lovely to chat with. We appreciated they allowed our 80 lb dog. She's not allowed on furniture so a good traveler.I would like to suggest a sponge, drying rack and towels in the kitchen. We did have to clean a few things before using...
United States
Kathy B.
The price is SAR 567
SAR 1,761 total
includes taxes & fees
26 Oct - 27 Oct
Farm Adventure | Animals + Fire Pit | Lakes Region
A narrow kitchen with a stove, white cabinets, and a wooden floor.

8. 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 SAR 642
SAR 1,486 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Cottage on a Lake, near Gunstock Mountain
A wooden cabin interior with a dining table, chairs, a sofa, and a TV.

9. 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 SAR 820
SAR 1,289 total
includes taxes & fees
19 Oct - 20 Oct
A - Farmhouse Apartment on a Cattle Farm
A cozy cabin interior with a sectional sofa, a leather ottoman, and a television mounted on the wall.

10. 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 SAR 694
SAR 1,551 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
A cozy room with a large window, a sofa, a coffee table, and a wicker chair.

11. 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 SAR 1,358
SAR 3,092 total
includes taxes & fees
2 Nov - 3 Nov
Locke Lake House
A modern interior with a large sliding glass door leading to an outdoor deck.

12. Cozy Long Pond Winter Retreat: Waterfront Gem!

Cozy Long Pond Winter Retreat: Waterfront Gem!
Barrington
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful and peaceful lakeside property, immaculately cleaned and stocked with everything you need for a relaxing time in New Hampshire. We thoroughly enjoyed our stay here and would return in a heartbeat!"
United States
Tina U.
The price is SAR 739
SAR 2,154 total
includes taxes & fees
23 Oct - 24 Oct
Cozy Long Pond Winter Retreat: Waterfront Gem!
A modern kitchen with a large island, dark cabinetry, and a view of the outdoors.

13. 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 SAR 615
SAR 1,341 total
includes taxes & fees
23 Oct - 24 Oct
Stay in Venice our Modern Steps from the Lake with Dock!
A living room with a view of a lake, featuring a leather sofa, a black armchair, and wicker chairs.

14. 4BR Dog-Friendly Lakefront, Private Dock, Kayaks, Paddleboards, Sleeps 8

4BR Dog-Friendly Lakefront, Private Dock, Kayaks, Paddleboards, Sleeps 8
Gilmanton
10.0 out of 10, Exceptional, (9 reviews)
"Incredible place, host was extremely thoughtful in providing extras for guests that was appreciated. Has everything you need and more. Highly recommend."
United States
Conor N.
The price is SAR 1,914
SAR 3,652 total
includes taxes & fees
28 Oct - 29 Oct
4BR Dog-Friendly Lakefront, Private Dock, Kayaks, Paddleboards, Sleeps 8
A sign for Cottages on Main, located at 324 Main Street, with a website address CottagesOnMain.com.

15. Newly Renovated Cottage 8 Main Street Alton Bay!

Newly Renovated Cottage 8 Main Street Alton Bay!
Alton
7.4 out of 10, Good, (6 reviews)
"My bed was broken to the point where I was sleeping at an angle & The couch bed was nasty it had stains and dirt all over it , The bunk beds were like taking a trip to bar heaven it was truly a painful stay"
United States
Eric
The price is SAR 612
SAR 1,222 total
includes taxes & fees
19 Oct - 20 Oct
Newly Renovated Cottage 8 Main Street Alton Bay!
A modern interior with a large sliding glass door leading to an outdoor deck.

16. 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 SAR 931
SAR 2,130 total
includes taxes & fees
23 Oct - 24 Oct
7 Mi to Hiking: Waterfront Long Pond Gem!
A modern kitchen with a central island, bar stools, hanging pendant lights, and a stainless steel refrigerator.

17. Serene Pondside Retreat Surrounded by Nature

Serene Pondside Retreat Surrounded by Nature
Deerfield
10.0 out of 10, Exceptional, (1 review)
"Wonderful property - we stayed here to visit our nearby family and attend opening day of the Deerfield fair. The property is immaculately maintained and the host responsive. We’ll be back!"
United States
Bobbi S.
The price is SAR 675
SAR 2,606 total
includes taxes & fees
20 Oct - 21 Oct
Serene Pondside Retreat Surrounded by Nature
A kitchen with a marble countertop, stainless steel sink, and a black pendant light.

18. Incredible Lake & Mtn Views - Loft Vibes Getaway!

Incredible Lake & Mtn Views - Loft Vibes Getaway!
Tilton
10.0 out of 10, Exceptional, (1 review)
"The location of this was perfect for us. We went to 2 nights of concerts at the pavilion and the drive was very easy. The location to food and activities was also great! The place was exactly as pictured, very clean, and perfect for our needs. The host was phenomenal, communicative, and even helped us out when we arrived with a flat tire! We look forward to making this "our spot" when we come up for concerts in the future!"
United States
Melissa S.
The price is SAR 475
SAR 1,065 total
includes taxes & fees
16 Nov - 17 Nov
Incredible Lake & Mtn Views - Loft Vibes Getaway!
A wooden sauna with a glass door, a shower area with shelves, and a red wall with a mirror.

19. Rustic Rose Cottage of Historic West Lebanon

Rustic Rose Cottage of Historic West Lebanon
Lebanon
9.8 out of 10, Exceptional, (31 reviews)
"Everything was great. Very clean and comfortable! Thank you for a great place to stay. "
United States
Heather K.
The price is SAR 390
SAR 871 total
includes taxes & fees
3 Nov - 4 Nov
Rustic Rose Cottage of Historic West Lebanon
A deck with wicker furniture, a table, and a view of a lake and trees.

20. Lakefront Bliss, Private Dock & Cozy Year-Round Retreat!

Lakefront Bliss, Private Dock & Cozy Year-Round Retreat!
Belmont
10.0 out of 10, Exceptional, (25 reviews)
"Great communication with host, everything was perfect. Perfect house for a family great location!! Hoping to get back for the summer and enjoy the lake! "
United States
Elizabeth K.
The price is SAR 1,115
SAR 2,301 total
includes taxes & fees
19 Oct - 20 Oct
Lakefront Bliss, Private Dock & Cozy Year-Round Retreat!
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
"Everything was great , we were very satisfied !"
James 4-night trip
Posted 1 hour ago
Comfort Inn Concord South End

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.