Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Pittsfield vacation rentals

Property grounds

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 ￥23,759
￥29,503 total
includes taxes & fees
Mar 4 - Mar 5
The Barn - Lake View and Pet Friendly
1 bedroom

Fully stocked camper with delivery/setup to your favorite campground/cabin/event

Fully stocked camper with delivery/setup to your favorite campground/cabin/event
New Durham
6.0 out of 10, (1 review)
"The ad said the camper was nearly new, which it was not. We had a time to meet Jake, but he came and left early so we didn't get an intro. It was okay cleanliness wise, except the refrigerator was gross, and the shower curtain had dead bugs wrapped up in it. The cabinets were all very full, so we didn't have any place to put our food without moving stuff around. Then we had ants. The bed was very comfortable. We slept great. This is what we wanted it for, so wasn't disappointed in that. We used...
United States
Cathy M.
The price is ￥15,293
￥73,991 total
includes taxes & fees
Mar 3 - Mar 4
Fully stocked camper with delivery/setup to your favorite campground/cabin/event
View from property

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
2.0 star property
Epsom
9.8 out of 10, Exceptional, (124 reviews)
"Very cozy cabin, fantastic experience "
United States
Hang
The price is ￥15,449
￥23,535 total
includes taxes & fees
Mar 3 - Mar 4
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Sauna

Rustic Rose Cottage of Historic West Lebanon

Rustic Rose Cottage of Historic West Lebanon
Lebanon
10.0 out of 10, Exceptional, (24 reviews)
"Everything about our stay was lovely! Check-in was smooth, the property was gorgeous, and the cottage was full of charm. "
United States
Daniel S.
The price is ￥15,449
￥35,550 total
includes taxes & fees
Mar 3 - Mar 4
Rustic Rose Cottage of Historic West Lebanon
Terrace/patio

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Wolfeboro
9.6 out of 10, Exceptional, (11 reviews)
"Great property. Loved our stay and the owners were great! Definitely will book again "
United States
Marcus
The price is ￥24,141
￥29,918 total
includes taxes & fees
Mar 3 - Mar 4
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Fridge, microwave, oven, stovetop

Idyllic Mountain and Lake Getaway

Idyllic Mountain and Lake Getaway
Gilford
10.0 out of 10, Exceptional, (73 reviews)
"Amazing spot!"
United States
David E.
The price is ￥63,200
￥97,695 total
includes taxes & fees
Mar 8 - Mar 9
Idyllic Mountain and Lake Getaway
Private kitchen

Cozy Cottage on a Lake, near Gunstock Mountain

Cozy Cottage on a Lake, near Gunstock Mountain
Gilmanton
9.4 out of 10, Exceptional, (3 reviews)
"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 "
United States
kim M.
The price is ￥26,685
￥60,108 total
includes taxes & fees
Mar 12 - Mar 13
Cozy Cottage on a Lake, near Gunstock Mountain
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!
Sanbornton
10.0 out of 10, Exceptional, (14 reviews)
"Great location, great kitchen, great bedding"
United States
Wanaka G.
The price is ￥49,156
￥113,102 total
includes taxes & fees
Mar 3 - Mar 4
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
Exterior

Modern Waterfront Condo with Views and Lake Access

Modern Waterfront Condo with Views and Lake Access
Tilton
9.6 out of 10, Exceptional, (11 reviews)
"Beautiful place, would be amazing to stay during the summer! "
United States
Liriana
The price is ￥20,224
￥53,606 total
includes taxes & fees
Mar 3 - Mar 4
Modern Waterfront Condo with Views and Lake Access
Terrace/patio

Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath

Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4 reviews)
"Everything was great!"
United States
Leah F.
The price is ￥45,645
￥55,958 total
includes taxes & fees
Mar 3 - Mar 4
Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
Sun loungers

5-Acre Home Near Gunstock Mountain & Lake Winnipesaukee w/ Mountain Views

5-Acre Home Near Gunstock Mountain & Lake Winnipesaukee w/ Mountain Views
Gilford
10.0 out of 10, Exceptional, (13 reviews)
"Was a great place to stay. Had a great time "
United States
Ryan C.
The price is ￥58,675
￥127,833 total
includes taxes & fees
Mar 3 - Mar 4
5-Acre Home Near Gunstock Mountain & Lake Winnipesaukee w/ Mountain Views
Terrace/patio

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 location, easy access and very clean. The only negative was the paper-thin walls or should I say neighbors that did not think of anyone else or their neighbors."
United States
Lisa D.
The price is ￥23,408
￥58,140 total
includes taxes & fees
Mar 15 - Mar 16
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Outdoor dining

[NEW] Cozy Cabin near Gunstock & Lake Winni

[NEW] Cozy Cabin near Gunstock & Lake Winni
Gilford
The price is ￥36,984
￥94,309 total
includes taxes & fees
Mar 4 - Mar 5
[NEW] Cozy Cabin near Gunstock & Lake Winni
Fridge, microwave, oven, stovetop

Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Skiing Location

Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Skiing Location
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 ￥35,892
￥79,410 total
includes taxes & fees
Mar 3 - Mar 4
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Skiing Location
Beach

Taigh Loch - Lakes Region Retreat!

Taigh Loch - Lakes Region Retreat!
Alton
9.8 out of 10, Exceptional, (15 reviews)
"Great place! Owners were very responsive with any questions we had. Per friendly was a plus. We would definitely stay here again."
United States
Shawn M.
The price is ￥19,506
￥53,335 total
includes taxes & fees
Mar 3 - Mar 4
Taigh Loch - Lakes Region Retreat!
Marina

Siena/Venice waterfront private units (2) with 2 Docks!

Siena/Venice waterfront private units (2) with 2 Docks!
Alton
The price is ￥71,627
￥126,653 total
includes taxes & fees
Mar 3 - Mar 4
Siena/Venice waterfront private units (2) with 2 Docks!
Interior

Lake Winni Waterfront Condo

Lake Winni Waterfront Condo
Gilford
The price is ￥29,735
￥59,389 total
includes taxes & fees
Mar 3 - Mar 4
Lake Winni Waterfront Condo
Outdoor dining

Lake Access + Kayaks + Arcade + Bike Path + Deck

Lake Access + Kayaks + Arcade + Bike Path + Deck
Wolfeboro
10.0 out of 10, Exceptional, (3 reviews)
"What you see is what you get and that's a very good thing!"
United States
john a.
The price is ￥17,166
￥49,779 total
includes taxes & fees
Mar 3 - Mar 4
Lake Access + Kayaks + Arcade + Bike Path + Deck
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, (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 ￥25,982
￥69,673 total
includes taxes & fees
Mar 3 - Mar 4
Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!
Terrace/patio

Peaceful Family Friendly Riverside Retreat w/ Gym, Hot Tub, Dock and Sunroom

Peaceful Family Friendly Riverside Retreat w/ Gym, Hot Tub, Dock and Sunroom
Webster
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful house with plenty of amenities and activities. Had a great time and would come back again!"
United States
Aleksa B.
The price is ￥56,989
￥146,999 total
includes taxes & fees
Mar 3 - Mar 4
Peaceful Family Friendly Riverside Retreat w/ Gym, Hot Tub, Dock and Sunroom
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

Best Western Concord Inn & Suites

Best Western Concord Inn & Suites

10/10 Excellent
"Room was clean. The staff was amazing nuce!!! I would stay there again."
darlene 1-night trip
Posted 1 day ago
Best Western Concord Inn & Suites

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

  • View our selection of featured holiday rentals in Pittsfield
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

Look no further and take a look at our great range of rental properties in Pittsfield!

Frequently asked questions

Can I find vacation rentals in Pittsfield?

Yes, there are vacation rentals close to popular local attractions in Pittsfield, or you can select a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Pittsfield has to offer?

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski: This vacation home rental outside of Pittsfield is located on a lake and has an indoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Pittsfield?

Expedia has 3 vacation rentals for your stay in Pittsfield.

What’s there to see and do in Pittsfield?

Lily Lake and Suncook River are a couple of scenic spots to enjoy the outdoors, whereas Scenic Theatre is one of the cultural attractions. Other places in town to visit include Josiah Carpenter Library and Pittsfield Town Hall.

What’s a vacation rental in Pittsfield like?

Vacation rentals are private properties you can stay in for short or long periods in Pittsfield. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.