Pittsfield Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Our top choices for Pittsfield vacation rentals

10.0 out of 10, Exceptional, (34)
"Even more beautiful than we were lead to hope for!Can’t wait to return with our entire family!"
United States
Mary Ann L.
Bower Cabin- Cabin in woods on a remote pond, Romantic getaway, Green living!
9.6 out of 10, Exceptional, (84)
"Everything was wonderful!!"
United States
Christina
$149 nightly
The price is $162
Dec 11 - Dec 12
Total with taxes and fees
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
10.0 out of 10, Exceptional, (15)
"We thoroughly enjoyed our stay at your cozy, clean, comfy cabin. It was a fun place to spend our couple of days of vacation "
United States
Jackie r.
Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi
8.6 out of 10, Excellent, (18)
"Location was A, however the overall place is very dated. One small pan to cook, along with a lobster pot. Furniture and bedding needs updating, along with interior. It is a great setting with lots of potential."
United States
Hubert B.
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
9.8 out of 10, Exceptional, (179)
"The house was amazing! The pool and sauna area felt like a resort. I am looking for an excuse to go back. "
United States
Maggie B.
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
9.4 out of 10, Exceptional, (25)
"Perfect waterfront stay but did not like being so close to the road."
United States
Lucas T.
$319 nightly
The price is $348
Dec 24 - Dec 25
Total with taxes and fees
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
8.6 out of 10, Excellent, (67)
"Convenient location, Host was great and responsive. Good place to be at with a few friends "
United States
Collin G.
$850 nightly
The price is $926
Dec 26 - Dec 27
Total with taxes and fees
New Lakefront Home sleeps 14 with dock.
10.0 out of 10, Exceptional, (15)
"Everything was great…and the hosts quickly responded to any requests for help with anything."
United States
William M.
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room
7.8 out of 10, Good, (45)
"The home was perfect for our stay! "
United States
Amy S.
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach
9.6 out of 10, Exceptional, (14)
"Very neat place"
United States
Scott
The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV
9.4 out of 10, Exceptional, (9)
"Great place to stay! Tons of games and fire pits all around. I wish we had stayed longer to enjoy it all."
United States
Tara L.
Cabin with lake views & lake access Now featuring AC Wi-FI and TV sleeps 5
9.4 out of 10, Exceptional, (3)
"Great house with a great location. Super responsive and having a slip to use makes the location perfect. "
United States
Ryan D.
New Charming Chalet with Lake Winni Views
9.8 out of 10, Exceptional, (16)
"We really enjoyed our stay at this property. It was very clean and well stocked and a nice location to get to activities around the lake.The host was very pleasant and easy to communicate with. We hope to stay again in the future."
United States
Linda N.
Come & enjoy beautiful Lake Winni! Concerts are within 5 min. Economy pricing
9.4 out of 10, Exceptional, (143)
"This was a great getaway spot for my husband and I to take a quick weekend trip! We came up for a concert, which was great as we were so close we walked over! Owner was wonderful and very responsive. We will definitely re book for the next lake trip or concert! "
United States
Sarah M.
Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni.
7.0 out of 10, Good, (33)
"Loved our stay."
United States
Judy C.
Waterfront home with wraparound deck, floating fireplace, deck, & firepit
10.0 out of 10, Exceptional, (1)
"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.
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
7.0 out of 10, Good, (12)
"Could be a wonderful house but hasn't been taken care of. Location is great. Website did not clearly indicate the 83 steps from the house to the lake. Loved the association beach and amenities."
United States
Laurie W.
Amazing lakefront retreat with stunning views - near skiing & golf
10.0 out of 10, Exceptional, (13)
"Great location, great kitchen, great bedding"
United States
Wanaka G.
$640 nightly
The price is $694
Dec 12 - Dec 13
Total with taxes and fees
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
9.8 out of 10, Exceptional, (40)
"This house and spot on the lake was just perfect! We loved everything about it. "
United States
Stacie R.
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

Vacation Home in Northwood

The Cottages at Harvey Lake
3.0 star property
8.8 out of 10, Excellent, (46)
"The cottage was great! It was very clean and comfy. The host had everything ready for us for a late check in. "
United States
Tonja
The Cottages at Harvey Lake
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pittsfield Hotel Reviews

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 $162 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.

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.