Holiday Homes in Pittsfield

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Our top choices for Pittsfield holiday homes

The Barn - Lake View and Pet Friendly

The Barn - Lake View and Pet Friendly
Pittsfield
6.0 out of 10, (1 review)
"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 €168
includes taxes & fees
27 May - 28 May
The Barn - Lake View and Pet Friendly

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

Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Alton
9.0 out of 10, Wonderful, (22 reviews)
"Great little gem given its price, location, and overall accommodations! "
United States
Kevin R.
The price is €251
includes taxes & fees
15 May - 16 May
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

Cozy hotel-style suite right on the water, shared patio, free WiFi

Cozy hotel-style suite right on the water, shared patio, free WiFi
Alton
8.8 out of 10, Excellent, (17 reviews)
"One of our favorite places to stay in this area."
United States
Anthony G.
The price is €251
includes taxes & fees
15 May - 16 May
Cozy hotel-style suite right on the water, shared patio, free WiFi

Stunning Lake Views close to Weirs Beach & Gunstock

Stunning Lake Views close to Weirs Beach & Gunstock
Weirs Beach
The price is €186
includes taxes & fees
18 May - 19 May
Stunning Lake Views close to Weirs Beach & Gunstock

Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
Cedar Lodge Room 2 Queen Beds & Private Balcony

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Alton
9.4 out of 10, Exceptional, (25 reviews)
"Great visit and property as described! Clean, all inclusive, and would recommend. View was beautiful and had a wonderful time."
United States
Catherine M.
The price is €361
includes taxes & fees
17 May - 18 May
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Room 4 (2nd Floor with Shared Bathroom)

Room 4 (2nd Floor with Shared Bathroom)
Weirs Beach
10.0 out of 10, Exceptional, (1 review)
"Clean, organized, great hospitality, location and views!"
United States
Troy D.
Room 4 (2nd Floor with Shared Bathroom)

[NEW] Cozy Cabin near Gunstock & Lake Winni

[NEW] Cozy Cabin near Gunstock & Lake Winni
Gilford
10.0 out of 10, Exceptional, (1 review)
"Great spot, especially for skiing at Gunstock. Very clean and comfortable. Host was available and responsive. Will definitely be coming back!"
United States
David H.
The price is €517
includes taxes & fees
18 May - 19 May
[NEW] Cozy Cabin near Gunstock & Lake Winni

The Cottages at Harvey Lake

The Cottages at Harvey Lake
3.0 star property
Northwood
8.8 out of 10, Excellent, (46 reviews)
"The view of the lake from the cabin was excellent. "
United States
Matt
The price is €126
includes taxes & fees
26 May - 27 May
The Cottages at Harvey Lake

Idyllic Mountain and Lake Getaway

Idyllic Mountain and Lake Getaway
Gilford
10.0 out of 10, Exceptional, (74 reviews)
"Would stay again"
United States
William D.
The price is €443
includes taxes & fees
27 May - 28 May
Idyllic Mountain and Lake Getaway

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

Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area
Downtown Laconia
9.8 out of 10, Exceptional, (36 reviews)
"Great place to stay, nice home right on the water led to a very relaxing stay "
United States
tyler g.
Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area

NEWER LAKEFRONT- 4 season home sleeps 6

NEWER LAKEFRONT- 4 season home sleeps 6
Alton
9.4 out of 10, Exceptional, (36 reviews)
"Very clean small house perfect for family of 4. Great Lake access. Property is even better than the photos. We would stay here again. "
United States
robert s.
The price is €469
includes taxes & fees
15 May - 16 May
NEWER LAKEFRONT- 4 season home sleeps 6

Lakefront Bliss, Private Dock & Cozy Year-Round Retreat!

Lakefront Bliss, Private Dock & Cozy Year-Round Retreat!
Belmont
10.0 out of 10, Exceptional, (16 reviews)
"This house on the lake is absolutely wonderful — spotless, well-equipped with everything you could possibly need, and beautifully maintained. The lake setting is very calming, surrounded by stunning natural scenery that changes with every season. Whether you’re visiting in summer to enjoy the water, this place is perfect year-round."
United States
Vitaliy P.
The price is €611
includes taxes & fees
4 Jun - 5 Jun
Lakefront Bliss, Private Dock & Cozy Year-Round Retreat!

Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!

Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!
New Durham
10.0 out of 10, Exceptional, (2 reviews)
"Suxhh a beautiful and well kept home. Relaxing there was our favorite part of the trip!"
United States
Justin G.
The price is €386
includes taxes & fees
17 May - 18 May
Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!

Cozy 3BR Lakefront House

Cozy 3BR Lakefront House
Laconia
Cozy 3BR Lakefront House

Attractive studio in waterfront location w/free WiFi, water views, kitchenette

Attractive studio in waterfront location w/free WiFi, water views, kitchenette
Alton
8.2 out of 10, Very good, (11 reviews)
"Loved everything, especially the price for such a perfect stay."
United States
John B.
The price is €251
includes taxes & fees
15 May - 16 May
Attractive studio in waterfront location w/free WiFi, water views, kitchenette

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
Alton
9.0 out of 10, Wonderful, (6 reviews)
"A quiet place with wonderful views. We stay here quiet often."
United States
Anthony G.
The price is €251
includes taxes & fees
15 May - 16 May
Terrific studio suite right on the water w/free WiFi, bay views, kitchenette

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
Alton
9.0 out of 10, Wonderful, (14 reviews)
"Just 2 days but very nice stay."
United States
Laura P.
The price is €251
includes taxes & fees
15 May - 16 May
Fabulous studio suite just a few steps from the water w/WiFi, bay views

Wonderful studio steps from the bay w/free WiFi, kitchenette, great water views

Wonderful studio steps from the bay w/free WiFi, kitchenette, great water views
Alton
7.6 out of 10, Good, (14 reviews)
"Awesome location, nice swimming area with dock. 3 grills so there is no wait time. On property caretaker answered any questions. "
United States
Jeffrey D.
The price is €251
includes taxes & fees
15 May - 16 May
Wonderful studio steps from the bay w/free WiFi, kitchenette, great water views

Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!

Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
Sanbornton
10.0 out of 10, Exceptional, (14 reviews)
"Great place for the extended family getaway. Clean, great location and has all the essentials you need.We had a great time with our teenage and young adults kids for NYE."
United States
Valerie A.
The price is €620
includes taxes & fees
23 May - 24 May
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
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

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
310
Accommodation
419 Holiday Homes
Lowest Price
€126
Highest Price
€620