Holiday Homes in Pittsfield

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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Featured Holiday Homes in Pittsfield

Exterior
The Barn - Lake View and Pet Friendly
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...
United States
Joseph G.
The price is AU$293
includes taxes & fees
1 Nov - 2 Nov
The Barn - Lake View and Pet Friendly
Exterior
The Coziest Tiny Home with Mini Cows & Horses!
The Coziest Tiny Home with Mini Cows & Horses!
9.4 out of 10, Exceptional, (19)
"Stayed for much needed adult getaway with my husband and it was exactly what we needed. It was quiet with everything we needed for a good time. We were able to bring our four-wheeler so that was nice. Looking out in the mornings with a coffee and watching the horses was so peaceful. I will definitely do this again! "
United States
Maranjellie A.
The price is AU$328
includes taxes & fees
31 Oct - 1 Nov
The Coziest Tiny Home with Mini Cows & Horses!
Outdoor dining
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
9.0 out of 10, Wonderful, (22)
"Excellent"
United States
Diane L.
The price is AU$437
includes taxes & fees
26 Oct - 27 Oct
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Marina
The Village of Paugus Bay Studio Close To It All!
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. "
United States
William
The price is AU$354
includes taxes & fees
24 Oct - 25 Oct
The Village of Paugus Bay Studio Close To It All!
Exterior
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
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."
United States
Christine F.
The price is AU$359
includes taxes & fees
29 Oct - 30 Oct
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
TV
Cozy hotel-style suite right on the water, shared patio, free WiFi
Cozy hotel-style suite right on the water, shared patio, free WiFi
8.8 out of 10, Excellent, (17)
"It is a very peaceful setting. "
United States
Priscilla
The price is AU$443
includes taxes & fees
26 Oct - 27 Oct
Cozy hotel-style suite right on the water, shared patio, free WiFi
Outdoor dining
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
9.8 out of 10, Exceptional, (37)
"Perfect for weekend getaway"
United States
Andrew E.
The price is AU$798
includes taxes & fees
27 Oct - 28 Oct
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
Dining
Lakeside Serenity! 3BR/2B Lake Front Retreat with Stunning Views
Lakeside Serenity! 3BR/2B Lake Front Retreat with Stunning Views
10.0 out of 10, Exceptional, (11)
"The house is superbly equipped and beautifully furnished. The host ist very friendly and easy to reach. We had a wonderful time. We loved the lake and the boats. "
Germany
Maja M.
The price is AU$637
includes taxes & fees
29 Oct - 30 Oct
Lakeside Serenity! 3BR/2B Lake Front Retreat with Stunning Views
Terrace/patio
Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area
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 "
United States
tyler g.
The price is AU$628
includes taxes & fees
26 Oct - 27 Oct
Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area
Terrace/patio
Idyllic Mountain and Lake Getaway
Idyllic Mountain and Lake Getaway
10.0 out of 10, Exceptional, (71)
"Beautiful property. We enjoyed our trip."
United States
DEBORAH
The price is AU$968
includes taxes & fees
27 Oct - 28 Oct
Idyllic Mountain and Lake Getaway
TV, stereo
Stay in Venice our Modern Steps from the Lake with Dock!
Stay in Venice our Modern Steps from the Lake with Dock!
10.0 out of 10, Exceptional, (7)
"Very clean and in a great location."
United States
Mark B.
The price is AU$589
includes taxes & fees
29 Oct - 30 Oct
Stay in Venice our Modern Steps from the Lake with Dock!
Smart TV, fireplace
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
10.0 out of 10, Exceptional, (12)
"The check-in process was easy. The house was beautiful and accommodated our family well. There was plenty of space for all of us. Communication with the host was easy, fast and efficient. Timothy was always able to help with any questions I had. The beds were super comfortable! And the house was decorated beautifully. "
United States
Denise G.
The price is AU$1,082
includes taxes & fees
24 Oct - 25 Oct
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
Smart TV, fireplace
Cool New Dover Home
Cool New Dover Home
10.0 out of 10, Exceptional, (8)
"Beautiful home and the property manager answered any questions very quickly. Everything went without a hitch. Check-in was flawless, the house was immaculate and extremely comfortable. They left water in the fridge (which we didn’t need), cute little toothbrushes and toothpaste in the bathrooms along with combs, shampoo, condition and body wash. This house had everything of we had forgotten something. "
United States
Charity R.
The price is AU$790
includes taxes & fees
26 Oct - 27 Oct
Cool New Dover Home
Outdoor dining
Fabulous studio suite just a few steps from the water w/WiFi, bay views
Fabulous studio suite just a few steps from the water w/WiFi, bay views
9.0 out of 10, Wonderful, (14)
"3rd year here and we will be back. Love the area, the room's, and the people"
United States
Courtney T.
The price is AU$437
includes taxes & fees
26 Oct - 27 Oct
Fabulous studio suite just a few steps from the water w/WiFi, bay views
Dining
Riverside Retreat w/ Hot Tub, Gym & Dock
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!"
United States
Neil A.
The price is AU$1,527
includes taxes & fees
27 Oct - 28 Oct
Riverside Retreat w/ Hot Tub, Gym & Dock
Outdoor spa tub
Blue Breeze - Private lakefront w/ Hot Tub
Blue Breeze - Private lakefront w/ Hot Tub
8.8 out of 10, Excellent, (3)
"My brother and I with his son stayed here while visiting family nearby. The house was clean and comfortable. When we arrived the lower level sliding glass door was open and I could not figure out how to lock it. Other than that I have no complaints. There was a snow storm during our stay, they cleared the driveway and stairs within 24 hours of the storm. The beds were comfortable and there were plenty of linens. We weren’t at the house much but the view was pretty. When we stopped for gas in our...
United States
Stephanie D.
The price is AU$969
includes taxes & fees
5 Nov - 6 Nov
Blue Breeze - Private lakefront w/ Hot Tub
Terrace/patio
Terrific studio suite right on the water w/free WiFi, bay views, kitchenette
Terrific studio suite right on the water w/free WiFi, bay views, kitchenette
9.0 out of 10, Wonderful, (6)
"A quiet place with wonderful views. We stay here quiet often."
United States
Anthony G.
The price is AU$437
includes taxes & fees
26 Oct - 27 Oct
Terrific studio suite right on the water w/free WiFi, bay views, kitchenette
Outdoor dining
Attractive studio in waterfront location w/free WiFi, water views, kitchenette
Attractive studio in waterfront location w/free WiFi, water views, kitchenette
8.2 out of 10, Very good, (11)
"Beautiful! We will return!"
United States
Christina
The price is AU$434
includes taxes & fees
27 Oct - 28 Oct
Attractive studio in waterfront location w/free WiFi, water views, kitchenette
Interior
Waterfront Home w/ Private Dock
Waterfront Home w/ Private Dock
10.0 out of 10, Exceptional, (20)
"Our family had a wonderful time at this lake house. It had everything we needed for cooking, playing in the lake and relaxing. Would definitely stay again! "
United States
Ashley H.
The price is AU$619
includes taxes & fees
26 Oct - 27 Oct
Waterfront Home w/ Private Dock
Fridge, microwave, oven, stovetop
Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath
Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath
9.6 out of 10, Exceptional, (17)
"Nice property, suitable for our needs. "
United States
Katie H.
The price is AU$972
includes taxes & fees
4 Nov - 5 Nov
Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath
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

Super 8 by Wyndham Tilton/Lake Winnipesaukee

Super 8 by Wyndham Tilton/Lake Winnipesaukee

10/10 Excellent
"Warm service, clean rooms"
Ofir 1-night trip
Posted 2 days ago
Super 8 by Wyndham Tilton/Lake Winnipesaukee

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
276
Accommodation
400 Holiday Homes
Lowest Price
AU$293
Highest Price
AU$1,527