Holiday Homes in Pittsfield

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Pittsfield and around

Our top choices for Pittsfield holiday homes

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 €227
includes taxes & fees
4 Sept - 5 Sept
The Barn - Lake View and Pet Friendly
The Cottages at Harvey Lake
Exterior

The Cottages at Harvey Lake

3.0 star property
8.8 out of 10, Excellent, (45)
"The view of the lake from the cabin was excellent. "
The price is €127
includes taxes & fees
1 Sept - 2 Sept
The Cottages at Harvey Lake
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 €248
includes taxes & fees
24 Aug - 25 Aug
Terrific studio suite right on the water w/free WiFi, bay views, kitchenette
Cozy hotel-style suite right on the water, shared patio, free WiFi
Property grounds

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

9.0 out of 10, Wonderful, (15)
"It is a very peaceful setting. "
Cozy hotel-style suite right on the water, shared patio, free WiFi
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 €178
includes taxes & fees
15 Sept - 16 Sept
Newly Renovated Cottage 4 in Alton Bay, NH
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

8.8 out of 10, Excellent, (16)
"Nice location on the lake."
The price is €273
includes taxes & fees
1 Sept - 2 Sept
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Newly Renovated Cottage 3 on Main Street Alton Bay!
Exterior

Newly Renovated Cottage 3 on Main Street Alton Bay!

The price is €179
includes taxes & fees
14 Sept - 15 Sept
Newly Renovated Cottage 3 on Main Street Alton Bay!
Cozy Cottage on a Lake, near Gunstock Mountain
Private kitchen

Cozy Cottage on a Lake, near Gunstock Mountain

10.0 out of 10, Exceptional, (1)
"The cabin is so cute and cozy! Very comfortable. We slept great! The neighbors were very friendly and even invited us over! The neighborhood is quiet and peaceful. The lake beach were amazing! We had a wonderful weekend getaway. The hosts are easy to contact. We will stay again! Love love the location! The only downside is there is no lake view from the cottage like we thought but easy lake access. We did not use the hot tub, washer/dryer or fire pit but those are great amenities! This place has...
The price is €386
includes taxes & fees
4 Sept - 5 Sept
Cozy Cottage on a Lake, near Gunstock Mountain
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Exterior

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

The price is €235
includes taxes & fees
4 Sept - 5 Sept
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
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"
Welcome to the Webster Place! A Charming 3-bedroom house in fabulous Franklin.
Stay in Venice our Modern Steps from the Lake with Dock!
TV, stereo

Stay in Venice our Modern Steps from the Lake with Dock!

10.0 out of 10, Exceptional, (6)
"Very clean and in a great location."
Stay in Venice our Modern Steps from the Lake with Dock!
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 €212
includes taxes & fees
16 Sept - 17 Sept
Spacious 2-bedroom Top Unit w/ Laundry 5 Mins to Downtown Concord
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, (8)
"Barbecue grill is something wrong because heating is so slow and not going up high a some time!"
Lakeside Serenity! 3BR/2B Lake Front Retreat with Stunning Views
Room 4 (2nd Floor with Shared Bathroom)
Terrace/patio

Room 4 (2nd Floor with Shared Bathroom)

10.0 out of 10, Exceptional, (1)
"Clean, organized, great hospitality, location and views!"
Room 4 (2nd Floor with Shared Bathroom)
Spacious Lake View Laconia Apt Near Weirs Beach\ Pool \ Restaurants
Marina

Spacious Lake View Laconia Apt Near Weirs Beach\ Pool \ Restaurants

Spacious Lake View Laconia Apt Near Weirs Beach\ Pool \ Restaurants
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, (1)
"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!"
Fall Foliage to explore on the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Hiking Location
Waterfront Home w/ Private Dock
Interior

Waterfront Home w/ Private Dock

10.0 out of 10, Exceptional, (18)
"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! "
The price is €352
includes taxes & fees
27 Aug - 28 Aug
Waterfront Home w/ Private Dock
Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath, sleeps10
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (12)
"Overall our stay was good and owner is super responsive. "
The price is €601
includes taxes & fees
16 Sept - 17 Sept
Lake, grill, s'mores, hike, golf! 4Bd 2.5Bath, sleeps10
Cool New Dover Home
Smart TV, fireplace

Cool New Dover Home

10.0 out of 10, Exceptional, (6)
The price is €443
includes taxes & fees
2 Sept - 3 Sept
Cool New Dover Home
The Coziest Tiny Home with Mini Cows & Horses!
Property grounds

The Coziest Tiny Home with Mini Cows & Horses!

9.6 out of 10, Exceptional, (15)
"Great sleeping!!!"
The price is €220
includes taxes & fees
1 Sept - 2 Sept
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.
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Top Pittsfield Hotel Reviews

Microtel Inn & Suites by Wyndham Dover

Microtel Inn & Suites by Wyndham Dover

10/10 Excellent
"We received a text so that I could take care of check in before we arrived. Once there, all I had to do was show my ID, sign a paper and receive the keys. It was just my daughter and I, we arrived pretty late. There were two very kind gentlemen there to welcome us. The water pressure upstairs was amazing. The water got nice and hot. The bed was comfortable and we both slept very well. The breakfast was nice. She had oatmeal and I had pancakes. Once again I received a text, this time so that I could check out online. Super easy and as we left I gave the key and they wished us a good day. My daughter goes to school at UNH, we were here for early move in. It’s about 18 minutes to campus. We will definitely use this location again! Thank you! "
Bernadette 1-night trip
Posted 2 days ago
Microtel Inn & Suites by Wyndham Dover