Pittsfield Holiday Rentals

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Check prices for these dates

Tonight
20 Aug - 21 Aug
Tomorrow
21 Aug - 22 Aug
This weekend
22 Aug - 24 Aug
Next weekend
29 Aug - 31 Aug

Holiday Rentals in Pittsfield

Our top choices for Pittsfield holiday rentals

Postcard Cabins Blake Brook
Exterior

Postcard Cabins Blake Brook

2.0 star property
9.8 out of 10, Exceptional, (46)
"Perfect place "
The price is HK$1,162
HK$1,557 total
includes taxes & fees
25 Aug - 26 Aug
Postcard Cabins Blake Brook
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Indoor pool

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

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

10.0 out of 10, Exceptional, (10)
"We enjoyed our time so much. My dogs roamed around and everyone was so kind and the fire pit was fantastic."
The price is HK$897
HK$2,014 total
includes taxes & fees
15 Sept - 16 Sept
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
Marina

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

9.8 out of 10, Exceptional, (11)
"Great place, quiet and immaculate~!"
The price is HK$796
HK$1,470 total
includes taxes & fees
9 Sept - 10 Sept
Cabin for two with lake views & access Now featuring AC Wi-FI and TV
Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni.
Outdoor dining

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

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 HK$1,170
HK$2,431 total
includes taxes & fees
25 Aug - 26 Aug
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Waterfront home with wraparound deck, floating fireplace, deck, & firepit
TV, DVD player

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

6.8 out of 10, (28)
"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
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Outdoor dining

Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

9.0 out of 10, Wonderful, (21)
"Excellent"
The price is HK$1,006
HK$2,200 total
includes taxes & fees
24 Aug - 25 Aug
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Secluded cozy Waterfront - Dams Beach
Property grounds

Secluded cozy Waterfront - Dams Beach

9.0 out of 10, Wonderful, (44)
"I came for Laconia bike week, and it was the perfect spot to be close to the action but also retreat when needed! Very relaxing and host was very accommodating!"
Secluded cozy Waterfront - Dams Beach
Cozy Cottage 2 Bedroom With Amazing View <br>
Interior

Cozy Cottage 2 Bedroom With Amazing View <br>

10.0 out of 10, Exceptional, (26)
"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>
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Terrace/patio

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 HK$1,786
HK$2,957 total
includes taxes & fees
10 Sept - 11 Sept
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
The Ultimate Getaway at a Charming Two-Bedroom Lakeside Cottage on Winnipesaukee
Marina

The Ultimate Getaway at a Charming Two-Bedroom Lakeside Cottage on Winnipesaukee

10.0 out of 10, Exceptional, (14)
"Great cottage right by the lake. Host was incredibly responsive and helpful. Fun back yard for games and grilling. 5/5 would recommend a stay here!"
The Ultimate Getaway at a Charming Two-Bedroom Lakeside Cottage on Winnipesaukee
Fabulous studio suite just a few steps from the water w/WiFi, bay views
Outdoor dining

Fabulous studio suite just a few steps from the water w/WiFi, bay views

9.0 out of 10, Wonderful, (14)
"Easy to find and beautiful spot on the lake. Highly recommended"
The price is HK$1,006
HK$2,191 total
includes taxes & fees
2 Sept - 3 Sept
Fabulous studio suite just a few steps from the water w/WiFi, bay views
New Lakefront Home sleeps 14 with dock.
Terrace/patio

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 HK$2,574
HK$5,149 total
includes taxes & fees
3 Sept - 4 Sept
New Lakefront Home sleeps 14 with dock.
🌟 Lakefront Bliss Awaits – Your Ultimate Getaway! 🏡🌊⛰️
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (27)
"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! 🏡🌊⛰️
🏖 Lake Winnipesaukee Vacation at Akwa Marina 🏖 Beach, Pool, Hot Tub, Beach Bar
Bar (on property)

🏖 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
Gorgeous Waterfront Condo with Lake Access & Views
Property grounds

Gorgeous Waterfront Condo with Lake Access & Views

9.8 out of 10, Exceptional, (31)
"Clean, quiet and an amazing location. "
The price is HK$1,040
HK$2,610 total
includes taxes & fees
15 Sept - 16 Sept
Gorgeous Waterfront Condo with Lake Access & Views
Modern & Cozy Lakefront Cabin: Rustic Charm and Serene views
Interior

Modern & Cozy Lakefront Cabin: Rustic Charm and Serene views

10.0 out of 10, Exceptional, (4)
"Very relaxing, great/easy waterfront access, terrific fishing, and very kid friendly! Hosts were very gracious and kept us informed the entire trip!"
The price is HK$3,003
HK$5,661 total
includes taxes & fees
3 Sept - 4 Sept
Modern & Cozy Lakefront Cabin: Rustic Charm and Serene views
The Cottages at Harvey Lake
Exterior

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 HK$1,061
HK$1,151 total
includes taxes & fees
3 Sept - 4 Sept
The Cottages at Harvey Lake
On Lake Winnipesaukee!,Year round house, private beach and great yard
Beach nearby, sun-loungers, beach towels

On Lake Winnipesaukee!,Year round house, private beach and great yard

8.6 out of 10, Excellent, (32)
"We had a great stay, great little beach area for young kids, a dock to moor a rented boat, huge lawn, beautiful sunsets, just a wonderful spot!"
On Lake Winnipesaukee!,Year round house, private beach and great yard
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

Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

10/10 Excellent
"Very hospitable and pleasant. "
Francis 1-night trip
Posted 20 hours ago
Best Western Plus Landmark Inn

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.