Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Holiday Rentals in Pittsfield

Postcard Cabins Blake Brook
Exterior

Postcard Cabins Blake Brook

2.0 star property
9.6 out of 10, Exceptional, (63)
"Amazing place for getaway!"
The price is HK$1,159
HK$1,554 total
includes taxes & fees
20 Oct - 21 Oct
Postcard Cabins Blake Brook
New Lakefront Home sleeps 14 with dock.
Terrace/patio

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
Indoor pool

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
Marina

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 HK$926
HK$2,102 total
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
Marina

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 HK$833
HK$1,517 total
includes taxes & fees
5 Oct - 6 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
Outdoor dining

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 HK$1,167
HK$2,417 total
includes taxes & fees
5 Oct - 6 Oct
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
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, (23)
"Loved the dock access and location. Easy check in and out !"
The price is HK$1,860
HK$3,510 total
includes taxes & fees
5 Oct - 6 Oct
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Cozy condo with WiFi, fitness room in enjoyable Laconia
Pool

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 HK$910
HK$2,347 total
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.
Outdoor dining

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
Fridge, microwave, oven, stovetop

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
Outdoor dining

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 HK$3,883
HK$4,804 total
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!
Exterior

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
TV

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 HK$1,004
HK$2,203 total
includes taxes & fees
5 Oct - 6 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
Beach

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 HK$833
HK$1,517 total
includes taxes & fees
5 Oct - 6 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
Dining

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
Outdoor dining

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 HK$2,103
HK$4,241 total
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
Exterior

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 HK$3,473
HK$9,695 total
includes taxes & fees
5 Oct - 6 Oct
Luxe 5 bd Home Near Lake Winnipesaukee
The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV
Beach

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 HK$1,650
HK$3,493 total
includes taxes & fees
5 Oct - 6 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
Outdoor spa tub

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! 🌅⛵️
Outdoor pool, a heated pool

🌟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

Steele Hill Resorts

Steele Hill Resorts

10/10 Excellent
"Relaxing, quite, beautiful view, friendly staff, will definitely return, and recommend both for families with children, or a quite retreat for us older folk, a weekend get away or extended stay"
Timothy 3-night trip
Posted 5 days ago
Steele Hill Resorts

Find out more about Pittsfield

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

  • View our selection of featured holiday rentals in Pittsfield
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

Look no further and take a look at our great range of rental properties in Pittsfield!

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.