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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Pittsfield holiday rentals

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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, (235 reviews)
"Good for couples"
United States
Julio
The price is AU$257
includes taxes & fees
28 Oct - 29 Oct
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
A cozy room with a large window, a sofa, a coffee table, and a wicker chair.

2. 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 AU$1,059
includes taxes & fees
1 Nov - 2 Nov
Locke Lake House
A wooden cabin interior with a dining table, chairs, a sofa, and a TV.

3. 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 AU$495
includes taxes & fees
26 Oct - 27 Oct
A - Farmhouse Apartment on a Cattle Farm
A living room with a view of a lake, featuring a leather sofa, a black armchair, and wicker chairs.

4. 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, (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 AU$1,236
includes taxes & fees
26 Oct - 27 Oct
4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock
cozy rustic bedroom

5. 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 AU$593
includes taxes & fees
1 Nov - 2 Nov
Farm Adventure | Animals + Fire Pit | Lakes Region
A spacious kitchen with a large island, white cabinetry, and a view of a playground through large windows.

6. 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, (8 reviews)
"Staff was very freindly"
United States
David
The price is AU$368
includes taxes & fees
1 Nov - 2 Nov
Newly Renovated Cottage 3 on Main Street Alton Bay!
A modern interior with a large sliding glass door leading to an outdoor deck.

7. 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 AU$808
includes taxes & fees
23 Oct - 24 Oct
7 Mi to Hiking: Waterfront Long Pond Gem!
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 AU$548
includes taxes & fees
2 Nov - 3 Nov
Cozy Cottage on a Lake, near Gunstock Mountain
A cabin with a wooden interior, a gray sofa with yellow cushions, a wooden bench, and a window with a view of trees and a snowy landscape.

9. New Lakefront Home sleeps 14 with dock.

New Lakefront Home sleeps 14 with dock.
Alton
8.6 out of 10, Excellent, (76 reviews)
"Plenty of parking, easy check in, plenty of sleeping areas and sitting areas. "
United States
Caroline M.
The price is AU$1,061
includes taxes & fees
2 Nov - 3 Nov
New Lakefront Home sleeps 14 with dock.
A modern interior with a large sliding glass door leading to an outdoor deck.

10. 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 AU$817
includes taxes & fees
23 Oct - 24 Oct
Cozy Long Pond Winter Retreat: Waterfront Gem!
A modern kitchen with a built-in microwave and oven, a gray sofa with teal cushions, and a view of a snowy landscape through large windows.

11. NEW Lakefront Escape Private Dock & Lake Views

NEW Lakefront Escape Private Dock & Lake Views
Alton
9.8 out of 10, Exceptional, (11 reviews)
"Beautiful location. Lake was beautiful and bedroom was right on the water. Responsive host."
United States
Magdalena P.
The price is AU$657
includes taxes & fees
19 Nov - 20 Nov
NEW Lakefront Escape Private Dock & Lake Views
A modern living room with a grey sofa, a floor lamp, and a hanging plant.

12. 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.
New, Clean, Downtown Getaway!
A cozy cabin interior with a sectional sofa, a leather ottoman, and a television mounted on the wall.

13. 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 AU$572
includes taxes & fees
31 Oct - 1 Nov
Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
A modern kitchen with a large island, dark cabinetry, and a view of the outdoors.

14. 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 AU$546
includes taxes & fees
5 Nov - 6 Nov
Stay in Venice our Modern Steps from the Lake with Dock!
Miscellaneous

15. 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 AU$265
includes taxes & fees
25 Oct - 26 Oct
Stone Haven "Tent Cabin" with a cast iron fire pit in Canterbury, NH.
A modern room with a spiral staircase, large sliding glass doors to a lake, and a desk with a chair.

16. Siena/Naples 2 units Sleeps 8 with 2 Docks!

Siena/Naples 2 units Sleeps 8 with 2 Docks!
Alton
8.6 out of 10, Excellent, (4 reviews)
"Excellent property right on the water. Easy walk to downtown. Would book again!"
United States
chris P.
The price is AU$970
includes taxes & fees
22 Nov - 23 Nov
Siena/Naples 2 units Sleeps 8 with 2 Docks!
A sign for Cottages on Main, located at 324 Main Street, with a website address CottagesOnMain.com.

17. 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 AU$533
includes taxes & fees
1 Nov - 2 Nov
Newly Renovated Cottage 8 Main Street Alton Bay!
A room with a large window, curtains, a bed, and a view of a forest and open field.

18. 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 AU$997
includes taxes & fees
26 Oct - 27 Oct
Serene Pondside Retreat Surrounded by Nature
A spacious living room with a sofa, a coffee table, and a TV. There is a kitchen area with a refrigerator and a stove.

19. 5-Acres, 1 Min to Gunstock, Beautiful Mtn Views, Hot Tub, Game Room + More!

5-Acres, 1 Min to Gunstock, Beautiful Mtn Views, Hot Tub, Game Room + More!
Gilford
9.8 out of 10, Exceptional, (26 reviews)
"Lovely country property! Perfect location for exploring the area! Hot tube was a plus. Beds were clean and comfortable!"
United States
Susan S.
The price is AU$1,135
includes taxes & fees
2 Nov - 3 Nov
5-Acres, 1 Min to Gunstock, Beautiful Mtn Views, Hot Tub, Game Room + More!
An outdoor deck with a wooden table set for a meal, a white sofa, and a small table with a lantern.

20. Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Private Ranch

Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Private Ranch
Gilford
10.0 out of 10, Exceptional, (3 reviews)
"We had a great time at the Wagner Ranch. The bedrooms were comfy and the kitchen had all necessary items. Definitely will stay there again. The hosts were Great!"
United States
dave b.
The price is AU$789
includes taxes & fees
26 Oct - 27 Oct
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Private Ranch
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

Weirs Beach Motel and Cottages

Weirs Beach Motel and Cottages

10/10 Excellent
"The staff was very helpful. Our room was clean and spacious. We liked the location as it was a 5 minute walk down to the Weirs area with all the shops and restaurants."
Robin 2-night trip
Posted 2 hours ago
Weirs Beach Motel and Cottages

Find out more about Pittsfield

Everything you need to know about Pittsfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pittsfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield holiday rentals we have selected for you start as low as AU$257 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski: This holiday home rental outside of Pittsfield is located on a lake, and has an indoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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?

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 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.