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, (38)
"Amazing place for getaway!"
The price is AU$308
includes taxes & fees
6 Aug - 7 Aug
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 AU$293
includes taxes & fees
3 Sept - 4 Sept
Cabin for two with lake views & access Now featuring AC Wi-FI and TV

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

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

9.6 out of 10, Exceptional, (21)
"Loved the dock access and location. Easy check in and out !"
The price is AU$647
includes taxes & fees
7 Aug - 8 Aug
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

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

10.0 out of 10, Exceptional, (9)
"We enjoyed our time so much. My dogs roamed around and everyone was so kind and the fire pit was fantastic."
The price is AU$426
includes taxes & fees
3 Sept - 4 Sept
Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi

Cozy Cottage 2 Bedroom With Amazing View <br>

10.0 out of 10, Exceptional, (24)
"This place was just as described and just what our little group was looking for. It was clean and convenient to all the main attractions of Lake Winnepesaki. "
Cozy Cottage 2 Bedroom With Amazing View <br>

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 AU$485
includes taxes & fees
12 Aug - 13 Aug
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

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

10.0 out of 10, Exceptional, (8)
"Great place to stay. Nice area, with easy access to anything you may need. The shower is wonderful, and the king size bed was very confortable."
The price is AU$436
includes taxes & fees
12 Aug - 13 Aug
Central modern condo studio - ~5min drive from Weirs Beach & NH Bank Pavilion.

Waterfront home with wraparound deck, floating fireplace, deck, & firepit

6.8 out of 10, (27)
"Just did a little getaway with some friends place was super cute and clean cute little area. Will definitely be booking for the summer."
Waterfront home with wraparound deck, floating fireplace, deck, & firepit

🏖 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

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.

New Lakefront Home sleeps 14 with dock.

8.6 out of 10, Excellent, (65)
"Overall we enjoyed our stay. The house suited us just fine, no complaints. "
The price is AU$907
includes taxes & fees
3 Sept - 4 Sept
New Lakefront Home sleeps 14 with dock.

The Cottages at Harvey Lake

3.0 star property
8.8 out of 10, Excellent, (45)
"The view of the lake from the cabin was excellent. "
The price is AU$228
includes taxes & fees
1 Sept - 2 Sept
The Cottages at Harvey Lake

Gorgeous Waterfront Condo with Lake Access & Views

9.8 out of 10, Exceptional, (29)
"Clean, quiet and an amazing location. "
The price is AU$585
includes taxes & fees
3 Sept - 4 Sept
Gorgeous Waterfront Condo with Lake Access & Views

Condo with WiFi, private beach, full kitchen, & outdoor pool

7.8 out of 10, Good, (37)
"Great for a younger couple wanting a bargain spot close to the many local attractions."
Condo with WiFi, private beach, full kitchen, & outdoor pool

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

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

9.0 out of 10, Wonderful, (6)
"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 AU$444
includes taxes & fees
17 Aug - 18 Aug
Terrific studio suite right on the water w/free WiFi, bay views, kitchenette

🌟 Lakefront Bliss Awaits – Your Ultimate Getaway! 🏡🌊⛰️

9.4 out of 10, Exceptional, (26)
"Our group of 8 enjoyed the spacious house and proximity to the lake. The no contact check in was great. "
🌟 Lakefront Bliss Awaits – Your Ultimate Getaway! 🏡🌊⛰️

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 AU$442
includes taxes & fees
11 Aug - 12 Aug
Cozy hotel-style suite right on the water, shared patio, free WiFi

Luxurious Cabin in the Woods

10.0 out of 10, Exceptional, (2)
"Very nice clean quiet and private real cozy"
The price is AU$361
includes taxes & fees
26 Aug - 27 Aug
Luxurious Cabin in the Woods
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

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 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.