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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Pittsfield vacation 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, (224 reviews)
"Great stay"
United States
Anthony
The price is CA $192
CA $270 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $178
CA $354 total
includes taxes & fees
Oct 29 - Oct 30
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.
The price is CA $156
CA $327 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $172
CA $523 total
includes taxes & fees
Oct 28 - Oct 29
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 CA $470
CA $937 total
includes taxes & fees
Oct 25 - Oct 26
Modern & Cozy Lakefront Cabin: Rustic Charm and Serene views
A wooden cabin interior with a dining table, chairs, a sofa, and a TV.

6. 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 CA $311
CA $510 total
includes taxes & fees
Oct 13 - Oct 14
A - Farmhouse Apartment on a Cattle Farm
A narrow kitchen with a stove, white cabinets, and a wooden floor.

7. 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 CA $243
CA $566 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Cottage on a Lake, near Gunstock Mountain
A modern living room with a grey sofa, a coffee table, and large windows offering a view of the outside.

8. 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 CA $178
CA $355 total
includes taxes & fees
Oct 22 - Oct 23
Charming Alton Bay Getaway – 1BR Cottage, Pool Access & Walk to Lake
A cozy room with a large window, a sofa, a coffee table, and a wicker chair.

9. 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 CA $523
CA $1,184 total
includes taxes & fees
Nov 4 - Nov 5
Locke Lake House
A cozy room with a hammock, wicker furniture, and a view of a lush garden.

10. 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 CA $319
CA $611 total
includes taxes & fees
Oct 12 - Oct 13
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
A modern kitchen with white cabinets, a microwave, and a stove.

11. 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 CA $166
CA $341 total
includes taxes & fees
Oct 19 - Oct 20
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
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 CA $263
CA $586 total
includes taxes & fees
Oct 12 - Oct 13
Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
A wooden cabin interior with a dining table set for four, surrounded by wooden chairs.

13. 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
On Baxter Lake: Wooded Retreat Near Trails
A dining room with a wooden table and chairs, a chandelier, and a vase with dried flowers.

14. My Sisters Place | Sleeps 6 • Piano & Pool Table

My Sisters Place | Sleeps 6 • Piano & Pool Table
Concord
The price is CA $213
CA $514 total
includes taxes & fees
Oct 12 - Oct 13
My Sisters Place | Sleeps 6 • Piano & Pool Table
A beach with clear water, a sandy shore, and a few trees in the background.

15. 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 CA $161
CA $288 total
includes taxes & fees
Oct 12 - Oct 13
Fantastic Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi
A residential property with a wooden deck, a small garden, and a blue house with a chimney.

16. 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 CA $193
CA $383 total
includes taxes & fees
Oct 12 - Oct 13
Newly Renovated Cottage on Main Street Alton Bay #5
A beach with clear water, a sandy shore, and a few trees in the background.

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

Delightful Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi
Alton
9.2 out of 10, Wonderful, (10 reviews)
"Pleasant cabin and great location"
United States
Richard T.
The price is CA $215
CA $485 total
includes taxes & fees
Oct 12 - Oct 13
Delightful Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi
A living room with a view of a lake, featuring a leather sofa, a black armchair, and wicker chairs.

18. 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 CA $640
CA $1,278 total
includes taxes & fees
Oct 12 - Oct 13
4BR Dog-Friendly Lakefront, Private Dock, Kayaks, Paddleboards, Sleeps 8
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 CA $275
CA $558 total
includes taxes & fees
Oct 22 - Oct 23
Stay in Venice our Modern Steps from the Lake with Dock!
A modern interior with a large sliding glass door leading to an outdoor deck.

20. 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 CA $280
CA $824 total
includes taxes & fees
Oct 23 - Oct 24
Cozy Long Pond Winter Retreat: Waterfront Gem!
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

Quality Inn Loudon-Concord

Quality Inn Loudon-Concord

10/10 Excellent
"Practical an peacefull."
GHEORGHE 1-night trip
Posted 4 hours ago
Quality Inn Loudon-Concord

Find out more about Pittsfield

Everything you need to know about Pittsfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pittsfield vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield vacation rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield vacation 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 vacation.

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 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.