Holiday Homes in Pittsfield

Start date: Check-in selected.
To Date
End date: Check-out
    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Featured Holiday Homes in Pittsfield

The Barn - Lake View and Pet Friendly
Exterior

The Barn - Lake View and Pet Friendly

6.0 out of 10, (1)
"It was peaceful and quiet, nice water view from the picture window , whole place was nice sized, Nice sized kitchen downstairs and office room, The main bathroom upstairs was nice and balcony was very nice, However the strong smell of animal urin all upstairs in the living room/bedroom was overwhelming, We brought our own lysol wipes to wipe everything down and used our Febreeze air spray to try to clean the smell upstairs , the little sofa looked stained and smelled, We sprayed it with...
The price is NZ$321
includes taxes & fees
7 Oct - 8 Oct
The Barn - Lake View and Pet Friendly
Newly Renovated Cottage 3 on Main Street Alton Bay!
Exterior

Newly Renovated Cottage 3 on Main Street Alton Bay!

10.0 out of 10, Exceptional, (1)
"Great little spot right next to the bay. Team was super responsive prior, during and after check in. Would highly recommend. "
The price is NZ$400
includes taxes & fees
5 Oct - 6 Oct
Newly Renovated Cottage 3 on Main Street Alton Bay!
Terrific studio suite right on the water w/free WiFi, bay views, kitchenette
Terrace/patio

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 NZ$486
includes taxes & fees
5 Oct - 6 Oct
Terrific studio suite right on the water w/free WiFi, bay views, kitchenette
The Village of Paugus Bay Studio Close To It All!
Marina

The Village of Paugus Bay Studio Close To It All!

9.0 out of 10, Wonderful, (9)
"Parking and access to the room was great, the view not so much. Overall it was perfect for our need and will definitely stay again in the future. "
The price is NZ$389
includes taxes & fees
29 Oct - 30 Oct
The Village of Paugus Bay Studio Close To It All!
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 NZ$486
includes taxes & fees
5 Oct - 6 Oct
Cozy hotel-style suite right on the water, shared patio, free WiFi
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 NZ$533
includes taxes & fees
5 Oct - 6 Oct
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Newly Renovated Cottage 4 in Alton Bay, NH
Private kitchen

Newly Renovated Cottage 4 in Alton Bay, NH

8.8 out of 10, Excellent, (3)
"Communication was amazing, check in was a delightful, the house itself was perfect "
The price is NZ$456
includes taxes & fees
5 Oct - 6 Oct
Newly Renovated Cottage 4 in Alton Bay, NH
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Exterior

Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!

10.0 out of 10, Exceptional, (1)
"This is a classic old-style cabin that reminded us of our childhood family trips in the 60’s. It’s not new, but a heck of a lot of fun if you’re in the right head space. Easily walked to town for dinner and to the shore. Clean and had everything we needed."
The price is NZ$402
includes taxes & fees
6 Oct - 7 Oct
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath, sleeps10
Fridge, microwave, oven, stovetop

Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath, sleeps10

9.6 out of 10, Exceptional, (15)
"Had a great stay. Property manager available anytime if needed. Nice property. Easy access. "
The price is NZ$1,018
includes taxes & fees
8 Oct - 9 Oct
Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath, sleeps10
Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area
Terrace/patio

Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area

9.8 out of 10, Exceptional, (33)
"Great place to stay, nice home right on the water led to a very relaxing stay "
The price is NZ$691
includes taxes & fees
14 Oct - 15 Oct
Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area
Welcome to the Webster Place! A Charming 3-bedroom house in fabulous Franklin.
Living area

Welcome to the Webster Place! A Charming 3-bedroom house in fabulous Franklin.

10.0 out of 10, Exceptional, (1)
"A great quite lake house With everything you need"
The price is NZ$595
includes taxes & fees
31 Oct - 1 Nov
Welcome to the Webster Place! A Charming 3-bedroom house in fabulous Franklin.
Lakeside Serenity! 3BR/2B Lake Front Retreat with Stunning Views
Dining

Lakeside Serenity! 3BR/2B Lake Front Retreat with Stunning Views

10.0 out of 10, Exceptional, (10)
"Modern interior, plenty of supplies and necessities, responsive owner, friendly, already hoping to come back in the future. The lake was phenomenal! Provided kayaks too. Great place "
The price is NZ$702
includes taxes & fees
3 Nov - 4 Nov
Lakeside Serenity! 3BR/2B Lake Front Retreat with Stunning Views
Cozy Cottage on a Lake, near Gunstock Mountain
Private kitchen

Cozy Cottage on a Lake, near Gunstock Mountain

9.0 out of 10, Wonderful, (2)
"We had a great time. Loved the cabin super cute. Neighborhood & neighbors very nice. The lake & private beaches were great. We enjoyed the hot tub & fire pit. I brought a few games, but you had a nice selection as well. Kitchen was very nice with everything we needed for some nice big breakfasts to start our day. We did run into a bit of a problem with the water running out. During showers, but we worked through it. Over all it was a great place. Thank you. Kim, Steve,Brianna,Cam & Brody "
The price is NZ$681
includes taxes & fees
14 Oct - 15 Oct
Cozy Cottage on a Lake, near Gunstock Mountain
Four Season Lake Escape Paugus Bay
Smart TV, fireplace

Four Season Lake Escape Paugus Bay

The price is NZ$759
includes taxes & fees
14 Oct - 15 Oct
Four Season Lake Escape Paugus Bay
Spacious 2-bedroom Top Unit w/ Laundry 5 Mins to Downtown Concord
Fridge, microwave, oven, stovetop

Spacious 2-bedroom Top Unit w/ Laundry 5 Mins to Downtown Concord

The price is NZ$421
includes taxes & fees
3 Nov - 4 Nov
Spacious 2-bedroom Top Unit w/ Laundry 5 Mins to Downtown Concord
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 NZ$948
includes taxes & fees
27 Oct - 28 Oct
Fall Foliage to explore on the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Hiking Location
Beautiful Lake Winnipesaukee w/ Dock!
Property grounds

Beautiful Lake Winnipesaukee w/ Dock!

10.0 out of 10, Exceptional, (2)
"This home has everything you need including a view of Paugus Bay in the Lakes Region. Although we were there on business, this lovely home was a pleasure to walk into at the end of customer meetings. You will be greeted by the view of the lake upon entering this sweet little oasis. It's clean, convenient, well appointed and spacious with the open concept. Megan addressed every question in a timely fashion. She seemed personable and welcoming. She takes great care of her home and I know she...
The price is NZ$912
includes taxes & fees
5 Oct - 6 Oct
Beautiful Lake Winnipesaukee w/ Dock!
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 NZ$773
includes taxes & fees
5 Oct - 6 Oct
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Riverside Retreat w/ Hot Tub, Gym & Dock
Dining

Riverside Retreat w/ Hot Tub, Gym & Dock

2.0 star property
10.0 out of 10, Exceptional, (4)
"The house was perfect! It fully met our expectations from the listing and was a great place to stay! There is a hot tub, sauna, gym, a comfy living room, and a functional kitchen! It was great, we had so much fun staying there. We were there in the Spring and had a blast, and could only imagine how awesome it would be in the winter with the fireplaces. I would strongly recommend staying here if it meets your needs!"
The price is NZ$1,712
includes taxes & fees
8 Oct - 9 Oct
Riverside Retreat w/ Hot Tub, Gym & Dock
The Coziest Tiny Home with Mini Cows & Horses!
Property grounds

The Coziest Tiny Home with Mini Cows & Horses!

9.4 out of 10, Exceptional, (18)
"Great sleeping!!!"
The price is NZ$401
includes taxes & fees
7 Oct - 8 Oct
The Coziest Tiny Home with Mini Cows & Horses!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

The Centennial

The Centennial

10/10 Excellent
"Great place. Convenient to downtown. Friendly staff "
Phil 1-night trip
Posted 3 days ago
The Centennial

Find out more about Pittsfield

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
125
Accommodation
400 Holiday Homes
Lowest Price
NZ$321
Highest Price
NZ$1,018

Explore a world of travel with Expedia

Explore a world of travel with Expedia