A calm lake reflecting colorful autumn trees and misty mountains in the distance.

Pittsfield Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Pittsfield vacation rentals

View from property

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, (177 reviews)
"What a great experience, everyone was so kind and the room was clean and comfortable with the staff"
United States
Katherin
$184 nightly
The price is $200
Aug 30 - Aug 31
Total with taxes and fees
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Lake

2. The Cottages at Harvey Lake

The Cottages at Harvey Lake
3.0 star property
Northwood
8.8 out of 10, Excellent, (47 reviews)
"The view of the lake from the cabin was excellent. "
United States
Matt
$152 nightly
The price is $165
Aug 5 - Aug 6
Total with taxes and fees
The Cottages at Harvey Lake
House (4 Bedrooms) | Interior

3. Quiet New Hampshire Getaway w/ Game Room!

Quiet New Hampshire Getaway w/ Game Room!
3.0 star property
Locke Lake Colony
$628 nightly
The price is $681
Aug 6 - Aug 7
Total with taxes and fees
Quiet New Hampshire Getaway w/ Game Room!
Interior

4. Lakefront Salmon Cottage

Lakefront Salmon Cottage
Northwood
9.8 out of 10, Exceptional, (16 reviews)
"Awesome place for quite getaway."
United States
Jason L.
$190 nightly
The price is $206
Aug 6 - Aug 7
Total with taxes and fees
Lakefront Salmon Cottage
Beach

5. Quiet New Hampshire Getaway w/ Game Room!

Quiet New Hampshire Getaway w/ Game Room!
Locke Lake Colony
10.0 out of 10, Exceptional, (11 reviews)
"Great location and comfortable beds."
United States
Terra K.
$642 nightly
The price is $697
Aug 6 - Aug 7
Total with taxes and fees
Quiet New Hampshire Getaway w/ Game Room!
Dining

6. Lakefront Yellow Cottage

Lakefront Yellow Cottage
Northwood
9.4 out of 10, Exceptional, (6 reviews)
"Clean, friendly, a great place to stay. I kayaked in the lake and it was beautiful. Hope to stay again next summer!"
United States
Ravaioli N.
$208 nightly
The price is $226
Aug 16 - Aug 17
Total with taxes and fees
Lakefront Yellow Cottage
Sun loungers

7. Lakes Region Cozy Camp in Shellcamp

Lakes Region Cozy Camp in Shellcamp
Gilmanton
9.8 out of 10, Exceptional, (26 reviews)
"Excellent and Know host. Great view. Very clean."
United States
Jonathan
$332 nightly
The price is $360
Aug 5 - Aug 6
Total with taxes and fees
Lakes Region Cozy Camp in Shellcamp
Dining

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

Hiking & Snowmobile Trails On-Site: Alton Retreat!
Alton
10.0 out of 10, Exceptional, (7 reviews)
"Such a cute place! Great amenities! Very cozy! Would definitely stay again! "
United States
Karolyn W.
$261 nightly
The price is $283
Aug 2 - Aug 3
Total with taxes and fees
Hiking & Snowmobile Trails On-Site: Alton Retreat!
Exterior

9. Lakefront Purple Cottage

Lakefront Purple Cottage
Northwood
9.2 out of 10, Wonderful, (7 reviews)
"Quaint colorful just right ."
United States
Susan B.
$181 nightly
The price is $196
Aug 31 - Sep 1
Total with taxes and fees
Lakefront Purple Cottage
Interior

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, (37 reviews)
"Lovely stay in a quiet area. The hot tub was great to unwind in after hiking in the area!"
United States
Cristofer V.
$420 nightly
The price is $456
Aug 13 - Aug 14
Total with taxes and fees
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Smart TV, fireplace, DVD player, books

11. 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, (4 reviews)
"This property was immaculate and even more beautiful than the photos. The kitchen was well appointed and had everything needed to prepare meals for 8 adults for a week. The host was very responsive and helpful. I highly recommend staying here."
United States
Melanie S.
$1,085 nightly
The price is $1,177
Aug 2 - Aug 3
Total with taxes and fees
4BR Dog-Friendly Lakefront, Private Dock, Kayaks, Paddleboards, Sleeps 8
Property grounds

12. Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
Gilmanton
10.0 out of 10, Exceptional, (62 reviews)
"Great place! "
United States
Taylor B.
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
House (2 Bedrooms) | Interior

13. 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
Aug 3 - Aug 4
Total with taxes and fees
7 Mi to Hiking: Waterfront Long Pond Gem!
TV, fireplace, books

14. Farmhouse Apartment on a Highland Cattle Farm - A

Farmhouse Apartment on a Highland Cattle Farm - A
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.
$362 nightly
The price is $389
Aug 24 - Aug 25
Total with taxes and fees
Farmhouse Apartment on a Highland Cattle Farm - A
TV

15. Newly Renovated Cottage 7 in Alton Bay

Newly Renovated Cottage 7 in Alton Bay
Alton
10.0 out of 10, Exceptional, (2 reviews)
"Host was responsive and the property was just close enough to enjoy laconia without a huge price premium. Its a simple cabin, but it did what we needed it to do. Gravel parking lot is not the best for motorcycles if i had to leave constructive feedback. Would rent again."
United States
fred j.
$451 nightly
The price is $491
Aug 25 - Aug 26
Total with taxes and fees
Newly Renovated Cottage 7 in Alton Bay
Outdoor dining

16. Cozy cottage get-away at Lake Winnipesaukee with swim access off dock

Cozy cottage get-away at Lake Winnipesaukee with swim access off dock
Alton
9.6 out of 10, Exceptional, (17 reviews)
"Cabin is in a great location, very quiet, very comfortable, with great features. Would definitely return again when I'm in the area."
United States
Barry
$396 nightly
The price is $430
Aug 2 - Aug 3
Total with taxes and fees
Cozy cottage get-away at Lake Winnipesaukee with swim access off dock
Beach

17. The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV

The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV
Alton
9.6 out of 10, Exceptional, (17 reviews)
"Great place loved the bikes and campfire area"
United States
Desiree S.
$627 nightly
The price is $683
Aug 5 - Aug 6
Total with taxes and fees
The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV
Exterior

18. Lakefront Orange Cottage

Lakefront Orange Cottage
Northwood
9.0 out of 10, Wonderful, (12 reviews)
"The personal touch and welcome gift was lovely z"
United States
Joyce
$172 nightly
The price is $187
Aug 19 - Aug 20
Total with taxes and fees
Lakefront Orange Cottage
Private kitchen

19. Cozy Cottage on a Lake, near Gunstock Mountain

Cozy Cottage on a Lake, near Gunstock Mountain
Gilmanton
8.8 out of 10, Excellent, (5 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
Aug 11 - Aug 12
Total with taxes and fees
Cozy Cottage on a Lake, near Gunstock Mountain
TV

20. 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.
$413 nightly
The price is $450
Aug 25 - Aug 26
Total with taxes and fees
Newly Renovated Cottage 4 in Alton Bay, NH
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Homewood Suites by Hilton Dover

Homewood Suites by Hilton Dover

10/10 Excellent
"Le déjeuner était très bien"
France 2-night trip
Posted 1 hour ago
Homewood Suites by Hilton Dover

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?

🌟 Lakefront Bliss Awaits – Your Ultimate Getaway! 🏡🌊⛰️: This vacation home rental outside of Pittsfield is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the hot tub in this rental home to help you unwind.

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?

Suncook River and Lily Lake 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.