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, (225 reviews)
"Great stay"
United States
Anthony
$175 nightly
The price is $190
Nov 9 - Nov 10
Total with taxes and fees
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
$224 nightly
The price is $244
Oct 29 - Oct 30
Total with taxes and fees
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.
$212 nightly
The price is $231
Oct 12 - Oct 13
Total with taxes and fees
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.
$334 nightly
The price is $364
Oct 21 - Oct 22
Total with taxes and fees
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.
$606 nightly
The price is $658
Oct 25 - Oct 26
Total with taxes and fees
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.
$331 nightly
The price is $355
Oct 13 - Oct 14
Total with taxes and fees
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.
$365 nightly
The price is $396
Oct 26 - Oct 27
Total with taxes and fees
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)
$225 nightly
The price is $245
Oct 12 - Oct 13
Total with taxes and fees
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.
$772 nightly
The price is $810
Nov 2 - Nov 3
Total with taxes and fees
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.
$397 nightly
The price is $431
Oct 12 - Oct 13
Total with taxes and fees
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.
$217 nightly
The price is $236
Oct 12 - Oct 13
Total with taxes and fees
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.
$381 nightly
The price is $413
Oct 12 - Oct 13
Total with taxes and fees
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
$347 nightly
The price is $363
Oct 12 - Oct 13
Total with taxes and fees
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.
$184 nightly
The price is $200
Oct 12 - Oct 13
Total with taxes and fees
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.
$240 nightly
The price is $261
Oct 12 - Oct 13
Total with taxes and fees
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.
$315 nightly
The price is $343
Oct 12 - Oct 13
Total with taxes and fees
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.
$828 nightly
The price is $898
Oct 12 - Oct 13
Total with taxes and fees
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.
$361 nightly
The price is $393
Oct 24 - Oct 25
Total with taxes and fees
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.
$529 nightly
The price is $574
Oct 12 - Oct 13
Total with taxes and fees
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

Super 8 by Wyndham Tilton/Lake Winnipesaukee

Super 8 by Wyndham Tilton/Lake Winnipesaukee

10/10 Excellent
"Modest budget hotel. But clean; it smelled okay, check-in was fast, and the staff was accommodating. Most importantly, the mattresses were encased. Have no complaints whatsoever."
ellen 1-night trip
Posted 8 hours ago
Super 8 by Wyndham Tilton/Lake Winnipesaukee

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Pittsfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $200 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.