Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

Postcard Cabins Blake Brook

2.0 star property
9.6 out of 10, Exceptional, (64)
"Amazing place for getaway!"
The price is AU$302
includes taxes & fees
8 Oct - 9 Oct
Postcard Cabins Blake Brook

New Lakefront Home sleeps 14 with dock.

8.6 out of 10, Excellent, (67)
"We had such a nice time! The lake is gorgeous and everything we hoped for."
New Lakefront Home sleeps 14 with dock.

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

9.8 out of 10, Exceptional, (177)
"Great place, beautiful view"
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

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

10.0 out of 10, Exceptional, (15)
"Very clean cabin! Loved having a little screened in porch! The chairs and fire pit right out front of our spot was an added bonus. The showers had great water pressure and were very clean! Would visit again."
The price is AU$413
includes taxes & fees
13 Oct - 14 Oct
Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi

Cabin for two with lake views & access Now featuring AC Wi-FI and TV

9.8 out of 10, Exceptional, (12)
"This is a step up from camping, but with a nice vibe. We had a nice view of the lake from the deck. The room was clean and cozy. This was exactly as described. Great location too!"
The price is AU$302
includes taxes & fees
6 Oct - 7 Oct
Cabin for two with lake views & access Now featuring AC Wi-FI and TV

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

8.6 out of 10, Excellent, (18)
"Nice location on the lake."
The price is AU$477
includes taxes & fees
13 Oct - 14 Oct
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

9.6 out of 10, Exceptional, (23)
"Loved the dock access and location. Easy check in and out !"
The price is AU$536
includes taxes & fees
19 Oct - 20 Oct
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Cozy condo with WiFi, fitness room in enjoyable Laconia

10.0 out of 10, Exceptional, (3)
"Beautiful condo spacious and clean beautiful views loved the pool and hot tub! "
The price is AU$475
includes taxes & fees
3 Nov - 4 Nov
Cozy condo with WiFi, fitness room in enjoyable Laconia

Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni.

9.4 out of 10, Exceptional, (143)
"Gloria's place was great for me and my wife. Hung out on the private beach and then went to a show at NH Bank Pavilion. Gloria was super easy to work with. Would stay here again."
Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni.

Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room

10.0 out of 10, Exceptional, (15)
"Amazing hosts as always. We had a wonderful stay."
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room

great location weirs beach area rental

9.4 out of 10, Exceptional, (26)
"The property was exactly as it was listed, The host was great"
The price is AU$945
includes taxes & fees
25 Oct - 26 Oct
great location weirs beach area rental

Charming and spacious lakefront home with 4 bedrooms, hot tub and pool table!

10.0 out of 10, Exceptional, (57)
"We very much enjoyed staying at this cottage. It reminded us of a location our family had on Hills Pond."
Charming and spacious lakefront home with 4 bedrooms, hot tub and pool table!

Cozy hotel-style suite right on the water, shared patio, free WiFi

9.0 out of 10, Wonderful, (16)
"It is a very peaceful setting. "
The price is AU$435
includes taxes & fees
6 Oct - 7 Oct
Cozy hotel-style suite right on the water, shared patio, free WiFi

A great cabin with lake views & access! Now Featuring AC/ Wi-Fi- & TV

9.4 out of 10, Exceptional, (13)
"Such a nice place to stay!"
The price is AU$299
includes taxes & fees
6 Oct - 7 Oct
A great cabin with lake views & access! Now Featuring AC/ Wi-Fi- & TV

Come & enjoy beautiful Lake Winni! Concerts are within 5 min. Economy pricing

9.8 out of 10, Exceptional, (16)
"Very nice place! So close to weirs beach! Definitely would go back! Very clean and accommodating "
Come & enjoy beautiful Lake Winni! Concerts are within 5 min. Economy pricing

Fall Foliage to explore on the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Hiking Location

10.0 out of 10, Exceptional, (2)
"We had a great time at the Wagner Ranch. The bedrooms were comfy and the kitchen had all necessary items. Definitely will stay there again. The hosts were Great!"
The price is AU$833
includes taxes & fees
26 Oct - 27 Oct
Fall Foliage to explore on the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Hiking Location

Luxe 5 bd Home Near Lake Winnipesaukee

9.2 out of 10, Wonderful, (5)
"Amazing place for a large family. Able to be together with space to be separate. Highly recommend "
The price is AU$1,909
includes taxes & fees
6 Oct - 7 Oct
Luxe 5 bd Home Near Lake Winnipesaukee

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

9.6 out of 10, Exceptional, (13)
"Very neat place"
The price is AU$689
includes taxes & fees
13 Oct - 14 Oct
The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV

Stargazer's retreat with hot tub & decks - near Ellacoya State Beach

8.0 out of 10, Very good, (39)
"Everything was clean, organize and had plenty of everything we needed in kitchen, bathroom, etc. The hot tub was a plus also!! Thank you for making our stay for our sons wedding an enjoyable one."
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach

🌟Lake Winni 4 Bedroom home at Akwa Marina! 🌅⛵️

10.0 out of 10, Exceptional, (34)
"The host was very responsive and the property was lovely. Great lunch down at the beach/pool bar."
🌟Lake Winni 4 Bedroom home at Akwa Marina! 🌅⛵️
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

Find out more about Pittsfield

Find out more about Pittsfield

Everything you need to know about Pittsfield holiday rentals

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

Pittsfield holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield holiday rentals we have selected for you start as low as AU$299 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield holiday 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 holiday.

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 holiday rentals in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pittsfield has to offer?

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski: This holiday home rental outside of Pittsfield is located on a lake, and has an indoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Pittsfield?

Expedia has 3 holiday 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 holiday rental in Pittsfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pittsfield. Holiday rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a small group gathering.