Holiday Rentals in Pittsfield

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Pittsfield

Bower Cabin- Cabin in woods on a remote pond, Romantic getaway, Green living!

10.0 out of 10, Exceptional, (28)
"We wanted a weekend of relaxation, and we got just that this place is amazing the pictures do not do it justice the hospitality the serene views we will be back next time in the summer."
Bower Cabin- Cabin in woods on a remote pond, Romantic getaway, Green living!

Postcard Cabins Blake Brook

2.0 star property
10.0 out of 10, Exceptional, (34)
"Amazing place for getaway!"
The price is €160
includes taxes & fees
28 Jul - 29 Jul
Postcard Cabins Blake Brook

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

9.8 out of 10, Exceptional, (9)
"Great place, quiet and immaculate~!"
The price is €187
includes taxes & fees
24 Aug - 25 Aug
Cabin for two with lake views & access Now featuring AC Wi-FI and TV

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

9.6 out of 10, Exceptional, (20)
"The place was quaint, modern and lovely. The views were fabulous! "
The price is €362
includes taxes & fees
24 Aug - 25 Aug
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

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

9.8 out of 10, Exceptional, (175)
"Fantastic stay! The house was spotless, beautifully decorated, and had all the amenities we needed for a comfortable stay. The location was perfect—close to everything yet peaceful and relaxing. The host was responsive and made the check-in process seamless. Highly recommend and would definitely stay again!"
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

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

8.8 out of 10, Excellent, (16)
"Nice location on the lake."
The price is €288
includes taxes & fees
6 Aug - 7 Aug
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

🏖 Lake Winnipesaukee Vacation at Akwa Marina 🏖 Beach, Pool, Hot Tub, Beach Bar

10.0 out of 10, Exceptional, (52)
"House was perfect lots to do, owners were great. Highly recommend to family’s"
🏖 Lake Winnipesaukee Vacation at Akwa Marina 🏖 Beach, Pool, Hot Tub, Beach Bar

Central modern condo studio - ~5min drive from Weirs Beach & NH Bank Pavilion.

10.0 out of 10, Exceptional, (5)
The price is €246
includes taxes & fees
4 Aug - 5 Aug
Central modern condo studio - ~5min drive from Weirs Beach & NH Bank Pavilion.

Gorgeous Waterfront Condo with Lake Access & Views

9.8 out of 10, Exceptional, (29)
"This was a great family vacation (with young kids). The location was perfect! The house had everything you need and the communication was excellent. We would love to come back and explore the area again!"
Gorgeous Waterfront Condo with Lake Access & Views

Luxurious Cabin in the Woods

10.0 out of 10, Exceptional, (2)
"Very nice clean quiet and private real cozy"
The price is €209
includes taxes & fees
4 Aug - 5 Aug
Luxurious Cabin in the Woods

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

9.4 out of 10, Exceptional, (139)
"Everything was clean & convenient. Such a beautiful beach also! "
Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni.

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

10.0 out of 10, Exceptional, (8)
"We enjoyed our time so much. My dogs roamed around and everyone was so kind and the fire pit was fantastic."
The price is €273
includes taxes & fees
30 Jul - 31 Jul
Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi

New Lakefront Home sleeps 14 with dock.

8.6 out of 10, Excellent, (64)
"Overall we enjoyed our stay. The house suited us just fine, no complaints. "
The price is €714
includes taxes & fees
21 Aug - 22 Aug
New Lakefront Home sleeps 14 with dock.

A cozy, relaxing, private cabin overlooking Sawyer Lake WIFI, TV, AC, Heat

9.6 out of 10, Exceptional, (42)
"Clean, close to the water with a great deck "
A cozy, relaxing, private cabin overlooking Sawyer Lake WIFI, TV, AC, Heat

Terrific studio suite right on the water w/free WiFi, bay views, kitchenette

8.8 out of 10, Excellent, (5)
"I loved that it was one the lake with private beach access!! The room could be better with a bigger bed not so hard."
The price is €246
includes taxes & fees
5 Aug - 6 Aug
Terrific studio suite right on the water w/free WiFi, bay views, kitchenette

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

9.0 out of 10, Wonderful, (14)
"It is a very peaceful setting. "
The price is €248
includes taxes & fees
27 Jul - 28 Jul
Cozy hotel-style suite right on the water, shared patio, free WiFi

Sunset-Facing Cottage on Mendums Pond in Barrington, NH

10.0 out of 10, Exceptional, (52)
"Beautiful setting on a quiet lake with loons and herons. We loved the deck overlooking the lake, and the kayaks and canoe provided (be sure to bring your own life vests)! The water was lovely and warm during our end-of-June stay."
Sunset-Facing Cottage on Mendums Pond in Barrington, NH

LAKE FRONT!! SKI ALL WINTER!!!

9.0 out of 10, Wonderful, (108)
"Great location, it was all we needed for our stay. The little private beach area at the lake was awesome and the water was beautiful! The layout of the house was great and felt very comfortable for 4 people. And the fans were appreciated! I would stay here again for sure."
LAKE FRONT!! SKI ALL WINTER!!!

Charming private cottage in Sanbornton with beach access to Lake Winnisquam.

10.0 out of 10, Exceptional, (2)
"Everything was very good"
Charming private cottage in Sanbornton with beach access to Lake Winnisquam.

Adorable Cabin with stunning lake views & Now featuring AC Wi-FI and TV access

9.2 out of 10, Wonderful, (5)
"We had an amazing stay, adorable area, loved the access to the lake and kayaking, close to great options for outdoor place. Looking forward to future trips"
The price is €220
includes taxes & fees
4 Aug - 5 Aug
Adorable Cabin with stunning lake views & Now featuring AC Wi-FI and TV access
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

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?

The Cottages at Harvey Lake: This holiday home rental outside of Pittsfield is located on the waterfront, and has a terrace, a garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchenette with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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.