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

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, (221 reviews)
"Great stay"
United States
Anthony
$184 nightly
The price is $200
Nov 1 - Nov 2
Total with taxes and fees
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
A modern interior with a large sliding glass door leading to an outdoor deck.

2. 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
$523 nightly
The price is $568
Oct 2 - Oct 3
Total with taxes and fees
7 Mi to Hiking: Waterfront Long Pond Gem!
A wide sandy beach with a calm lake and dense green trees in the background.

3. Quiet New Hampshire Getaway w/ Game Room!

Quiet New Hampshire Getaway w/ Game Room!
Locke Lake Colony
9.4 out of 10, Exceptional, (13 reviews)
"Great location and comfortable beds."
United States
Terra K.
Quiet New Hampshire Getaway w/ Game Room!
A cozy room with a hammock, wicker furniture, and a view of a lush garden.

4. 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, (44 reviews)
"Lovely stay in a quiet area. The hot tub was great to unwind in after hiking in the area!"
United States
Cristofer V.
$394 nightly
The price is $428
Oct 12 - Oct 13
Total with taxes and fees
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
A wooden cabin interior with a dining table, chairs, a sofa, and a TV.

5. 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 22 - Oct 23
Total with taxes and fees
A - Farmhouse Apartment on a Cattle Farm
A coastal town with a marina, a large cruise ship docked, and a beach.

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

Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi
Alton
10.0 out of 10, Exceptional, (19 reviews)
"Everyone was very comfortable and liked the location."
United States
Matt S.
$281 nightly
The price is $306
Oct 8 - Oct 9
Total with taxes and fees
Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi
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.
$367 nightly
The price is $398
Oct 5 - Oct 6
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 7 - Oct 8
Total with taxes and fees
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.

9. 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 2 - Oct 3
Total with taxes and fees
Cozy Long Pond Winter Retreat: Waterfront Gem!
A cozy room with a large window, a sofa, a coffee table, and a wicker chair.

10. 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.
$828 nightly
The price is $870
Nov 1 - Nov 2
Total with taxes and fees
Locke Lake House
A modern kitchen with a large island, dark cabinetry, and a view of the outdoors.

11. 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.
$328 nightly
The price is $357
Oct 8 - Oct 9
Total with taxes and fees
Stay in Venice our Modern Steps from the Lake with Dock!
A wide sandy beach with a calm lake and dense green trees in the background.

12. Quiet New Hampshire Getaway w/ Game Room!

Quiet New Hampshire Getaway w/ Game Room!
3.0 star property
Locke Lake Colony
Quiet New Hampshire Getaway w/ Game Room!
A lakeside deck with a fire feature, seating, and a view of boats on the water.

13. New Dreamy Lake Front Home

New Dreamy Lake Front Home
Alton
9.0 out of 10, Wonderful, (12 reviews)
"Great time with family. "
United States
Eddie C.
$659 nightly
The price is $718
Oct 5 - Oct 6
Total with taxes and fees
New Dreamy Lake Front Home
A cozy room with a wicker sofa, a wooden ladder shelf, and a large wooden-framed window.

14. 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.
$332 nightly
The price is $362
Oct 21 - Oct 22
Total with taxes and fees
Newly Renovated Cottage 4 in Alton Bay, NH
A living room with a view of a lake, featuring a leather sofa, a black armchair, and wicker chairs.

15. 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 7 - Oct 8
Total with taxes and fees
4BR Dog-Friendly Lakefront, Private Dock, Kayaks, Paddleboards, Sleeps 8
A modern living room with a grey sofa, a floor lamp, and a hanging plant.

16. 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.
$164 nightly
The price is $178
Oct 4 - Oct 5
Total with taxes and fees
New, Clean, Downtown Getaway!
A wooden cabin interior with a dining table set for four, surrounded by wooden chairs.

17. 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
$431 nightly
The price is $468
Oct 5 - Oct 6
Total with taxes and fees
On Baxter Lake: Wooded Retreat Near Trails
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.

18. New Lakefront Home sleeps 14 with dock.

New Lakefront Home sleeps 14 with dock.
Alton
8.8 out of 10, Excellent, (75 reviews)
"Plenty of parking, easy check in, plenty of sleeping areas and sitting areas. "
United States
Caroline M.
$671 nightly
The price is $731
Oct 4 - Oct 5
Total with taxes and fees
New Lakefront Home sleeps 14 with dock.
A cozy cabin interior with a sectional sofa, a leather ottoman, and a television mounted on the wall.

19. 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 4 - Oct 5
Total with taxes and fees
Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
A riverside dock with boats, a small house, and dense forest.

20. Cabin 21 at Historic Sandy Point Resort W/ Boat Slip and onsite Boat Ramp

Cabin 21 at Historic Sandy Point Resort W/ Boat Slip and onsite Boat Ramp
Alton
$473 nightly
The price is $515
Oct 7 - Oct 8
Total with taxes and fees
Cabin 21 at Historic Sandy Point Resort W/ Boat Slip and onsite Boat Ramp
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

The Centennial

The Centennial

8/10 Good
"Everything was pretty except for the water pressure in the shower. I would have appreciated if they had proper water flow/pressure. I felt cold while taking shower which is not the experience I want visiting the east coast."
Ankitaben 1-night trip
Posted 15 hours ago
The Centennial

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.