A calm lake reflecting colorful autumn trees and misty mountains in the distance.

Holiday Homes in Pittsfield

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Pittsfield holiday homes

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
Alton
8.8 out of 10, Excellent, (15 reviews)
"Just 2 days but very nice stay."
United States
Laura P.
The price is €276
includes taxes & fees
28 Jul - 29 Jul
Fabulous studio suite just a few steps from the water w/WiFi, bay views
Marina

Gilford Laconia Condo, Parking, Pool, WiFi & BBQ

Gilford Laconia Condo, Parking, Pool, WiFi & BBQ
Laconia
9.4 out of 10, Exceptional, (3 reviews)
"Great host, clear instructions, great location and great space, view of the lake was awesome"
United States
Dave D.
The price is €271
includes taxes & fees
16 Jul - 17 Jul
Gilford Laconia Condo, Parking, Pool, WiFi & BBQ
Exterior

Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is €207
includes taxes & fees
1 Jul - 2 Jul
Cedar Lodge Room 2 Queen Beds & Private Balcony
Property grounds

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, (18 reviews)
"One of our favorite places to stay in this area."
United States
Anthony G.
The price is €277
includes taxes & fees
6 Jul - 7 Jul
Cozy hotel-style suite right on the water, shared patio, free WiFi
TV, books

On Baxter Lake: Wooded Retreat Near Trails

On Baxter Lake: Wooded Retreat Near Trails
Farmington
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful and cozy little property! We really enjoyed our stay."
United States
Rebekah
On Baxter Lake: Wooded Retreat Near Trails
Living area

Gilford Getaway - Sleeps 8 - Minutes to Gunstock & Pavilion

Gilford Getaway - Sleeps 8 - Minutes to Gunstock & Pavilion
Gilford
Gilford Getaway - Sleeps 8 - Minutes to Gunstock & Pavilion
Lake

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 €155
includes taxes & fees
8 Jul - 9 Jul
The Cottages at Harvey Lake
TV, fireplace, video games, table football

Cozy Long Pond Winter Retreat: Waterfront Gem!

Cozy Long Pond Winter Retreat: Waterfront Gem!
Barrington
9.4 out of 10, Exceptional, (8 reviews)
"We had a lovely time! The place was beautiful, clean, and well equipped (with kayaks/life jackets, fishing gear, and games). The pond is gorgeous and has plenty of ducks, turtles and fish. "
United States
Alexander H.
The price is €510
includes taxes & fees
27 Jul - 28 Jul
Cozy Long Pond Winter Retreat: Waterfront Gem!
Terrace/patio

Room 11 (3rd Floor Shared Bathroom)

Room 11 (3rd Floor Shared Bathroom)
Weirs Beach
10.0 out of 10, Exceptional, (10 reviews)
"Great views of the lake, lots of outdoor seating and table to enjoy a meal and drink. The owner was very nice and hospitable. "
United States
Roger
The price is €201
includes taxes & fees
1 Jul - 2 Jul
Room 11 (3rd Floor Shared Bathroom)
Terrace/patio

Lakes Region Retreat | Fire Pit | Alton Bay

Lakes Region Retreat | Fire Pit | Alton Bay
Alton
Lakes Region Retreat | Fire Pit | Alton Bay
Marina

Paugus Bay Studio Close To It All!

Paugus Bay Studio Close To It All!
Gilford
7.0 out of 10, Good, (4 reviews)
"Convenient location to shops, restaurants and more!"
United Kingdom
Clerissa C.
The price is €320
includes taxes & fees
1 Jul - 2 Jul
Paugus Bay Studio Close To It All!
Fridge, microwave, oven, stovetop

Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Private Ranch

Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Private Ranch
Gilford
10.0 out of 10, Exceptional, (2 reviews)
"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!"
United States
dave b.
The price is €485
includes taxes & fees
1 Jul - 2 Jul
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Private Ranch
Sauna

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, (3 reviews)
"Great location in the woods! House was roomy and very comfortable..Host was very accommodating and communicated promptly and thoroughly. Lots of beds for the family!"
United States
Mary T.
The price is €559
includes taxes & fees
14 Jul - 15 Jul
Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!
Pool

Scenic Lakeside Condo with Lake Views Near Gunstock & Weirs Beach | Laconia, NH

Scenic Lakeside Condo with Lake Views Near Gunstock & Weirs Beach | Laconia, NH
Weirs Beach
The price is €235
includes taxes & fees
1 Jul - 2 Jul
Scenic Lakeside Condo with Lake Views Near Gunstock & Weirs Beach | Laconia, NH
Exterior

Peaceful Getaway Close to Lake Boating, Hiking, Skiing

Peaceful Getaway Close to Lake Boating, Hiking, Skiing
Alton
9.4 out of 10, Exceptional, (3 reviews)
"Great views"
United States
Sherry M.
The price is €556
includes taxes & fees
6 Jul - 7 Jul
Peaceful Getaway Close to Lake Boating, Hiking, Skiing
TV, stereo

New Lakefront Home sleeps 14 with dock.

New Lakefront Home sleeps 14 with dock.
Alton
8.6 out of 10, Excellent, (68 reviews)
"Plenty of parking, easy check in, plenty of sleeping areas and sitting areas. "
United States
Caroline M.
The price is €775
includes taxes & fees
1 Jul - 2 Jul
New Lakefront Home sleeps 14 with dock.
Terrace/patio

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. "
United States
Zack W.
The price is €545
includes taxes & fees
12 Jul - 13 Jul
Waterfront with Kayaks, Pool Table, Fire Pit, and Pergola. Downtown area
Outdoor dining

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 €277
includes taxes & fees
7 Jul - 8 Jul
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Smart TV, video games, ping pong, stereo

5 Bedroom Home Pool & Hot Tub

5 Bedroom Home Pool & Hot Tub
Dover
10.0 out of 10, Exceptional, (1 review)
"Stayed here for two nights while visiting at UNH. Location wise was about 20 minutes from the campus which was an easy commute. The best part was how spacious the house was. Lots of beds which was great for our large group. House was clean, well stocked and the basement set up for watching tv was amazing. The host was awesome to deal with, very responsive and checked in to make sure things were going well. Would stay again! "
Canada
Ken M.
The price is €985
includes taxes & fees
12 Jul - 13 Jul
5 Bedroom Home Pool & 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
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 €277
includes taxes & fees
6 Jul - 7 Jul
Terrific studio suite right on the water w/free WiFi, bay views, kitchenette
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

The Wolfeboro Inn

The Wolfeboro Inn

10/10 Excellent
"Room was small but clean and bed comfortable. Cardboard in small window allowed noise in from the street, probably missed during renovation, which has improved things significantly. Nice small private beach, but shed containing chairs was smelly and contained a wasp nest with wasps. Plenty of parking. WiFi weak and sporadic. No greeter at the tavern for dinner. Had to track down someone; place was mostly empty at dinner time. Server took our drink order and returned later to take it again. Mind you there was only one other couple in the room. Dinner was ok, sub-par Cobb salad but decent clam chowder. This morning, breakfast was the opposite. Warm greeting, excellent attentive server, great breakfast."
Frank 2-night trip
Posted 4 hours ago
The Wolfeboro Inn

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
247
Accommodation
485 Holiday Homes
Lowest Price
€155
Highest Price
€985