Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

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 ￥25,107
￥30,701 total
includes taxes & fees
May 11 - May 12
The Barn - Lake View and Pet Friendly
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
9.6 out of 10, Exceptional, (143 reviews)
"Great stay "
United States
Edward
The price is ￥22,180
￥30,991 total
includes taxes & fees
Apr 30 - May 1
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Marina

Cabin for two with lake views & access Now featuring AC Wi-FI and TV

Cabin for two with lake views & access Now featuring AC Wi-FI and TV
Alton
9.4 out of 10, Exceptional, (13 reviews)
"Easy check in, beautiful lake view and plenty dlto do in the area. "
United States
Michele D.
The price is ￥16,260
￥29,870 total
includes taxes & fees
Apr 30 - May 1
Cabin for two with lake views & access Now featuring AC Wi-FI and TV
Pool

Inviting condo in quiet locale with partial lake views, balcony & grilling area

Inviting condo in quiet locale with partial lake views, balcony & grilling area
Gilford
8.4 out of 10, Very Good, (17 reviews)
"Everything was just as listed, full amenities and cleanliness."
United States
John C.
The price is ￥11,159
￥42,171 total
includes taxes & fees
May 10 - May 11
Inviting condo in quiet locale with partial lake views, balcony & grilling area
Sauna

Rustic Rose Cottage of Historic West Lebanon

Rustic Rose Cottage of Historic West Lebanon
Lebanon
10.0 out of 10, Exceptional, (25 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 ￥15,782
￥36,142 total
includes taxes & fees
May 3 - May 4
Rustic Rose Cottage of Historic West Lebanon
TV, table tennis

Cute Cedar Lodge Studio with Balcony & Lake Views!

Cute Cedar Lodge Studio with Balcony & Lake Views!
Weirs Beach
9.6 out of 10, Exceptional, (16 reviews)
"Enjoyed our stay. "
United States
Ilene T.
The price is ￥12,111
￥30,573 total
includes taxes & fees
May 6 - May 7
Cute Cedar Lodge Studio with Balcony & Lake Views!
TV

Newly Renovated Cottage 7 in Alton Bay

Newly Renovated Cottage 7 in Alton Bay
Alton
10.0 out of 10, Exceptional, (1 review)
"endroit magnifique,emplacement agréable avec commodité sur place et près du lac et restaurant."
Canada
Alexandra R.
The price is ￥18,332
￥38,207 total
includes taxes & fees
May 14 - May 15
Newly Renovated Cottage 7 in Alton Bay
Property grounds

2BR Getaway in the Heart of the Lakes Region

2BR Getaway in the Heart of the Lakes Region
Weirs Beach
The price is ￥13,390
￥31,134 total
includes taxes & fees
Apr 30 - May 1
2BR Getaway in the Heart of the Lakes Region
Marina

2 Bdrm Condo walking distance to Weirs Beach and much more!!

2 Bdrm Condo walking distance to Weirs Beach and much more!!
Weirs Beach
9.6 out of 10, Exceptional, (55 reviews)
"Great location, easy and smooth stay!"
United States
Aimee M.
The price is ￥16,675
￥44,566 total
includes taxes & fees
Apr 30 - May 1
2 Bdrm Condo walking distance to Weirs Beach and much more!!
Marina

Cute 2 Bdrm Condo walking distance to Weirs Beach

Cute 2 Bdrm Condo walking distance to Weirs Beach
Weirs Beach
The price is ￥16,658
￥44,521 total
includes taxes & fees
Apr 30 - May 1
Cute 2 Bdrm Condo walking distance to Weirs Beach
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 ￥20,564
￥45,912 total
includes taxes & fees
May 3 - May 4
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Terrace/patio

Gorgeous Waterfront Condo with Lake Access & Views

Gorgeous Waterfront Condo with Lake Access & Views
Tilton
9.8 out of 10, Exceptional, (38 reviews)
"Great area, lake side is beautiful, responsive host. "
United States
jamie
The price is ￥16,350
￥47,346 total
includes taxes & fees
Apr 30 - May 1
Gorgeous Waterfront Condo with Lake Access & Views
Smart TV, video games

Cozy condo with WiFi, fitness room in enjoyable Laconia

Cozy condo with WiFi, fitness room in enjoyable Laconia
Weirs Beach
9.2 out of 10, Wonderful, (7 reviews)
"The condo was clean and much larger than expected! We had a wonderful stay! "
United States
Beth M.
The price is ￥15,208
￥43,655 total
includes taxes & fees
May 5 - May 6
Cozy condo with WiFi, fitness room in enjoyable Laconia
TV

Newly Renovated Cottage 4 in Alton Bay, NH

Newly Renovated Cottage 4 in Alton Bay, NH
Alton
9.0 out of 10, Wonderful, (4 reviews)
"Communication was amazing, check in was a delightful, the house itself was perfect "
United States
Jennifer S.
The price is ￥19,148
￥58,062 total
includes taxes & fees
May 19 - May 20
Newly Renovated Cottage 4 in Alton Bay, NH
Sun loungers, beach towels

Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
Gilford
9.6 out of 10, Exceptional, (23 reviews)
"a cute spot for an easy quick stay - close to all attractions. Quiet and clean and great communication with host. "
United States
Leah C.
The price is ￥18,351
￥38,438 total
includes taxes & fees
May 19 - May 20
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
Beach

Adorable Cabin with stunning lake views & Now featuring AC Wi-FI and TV access

Adorable Cabin with stunning lake views & Now featuring AC Wi-FI and TV access
Alton
9.2 out of 10, Wonderful, (7 reviews)
"We had an amazing stay, adorable area, loved the access to the lake and kayaking, close to great options for outdoor place. Looking forward to future trips"
United States
Amy S.
The price is ￥18,173
￥32,129 total
includes taxes & fees
May 10 - May 11
Adorable Cabin with stunning lake views & Now featuring AC Wi-FI and TV access
Pool

Weirs beach retreat

Weirs beach retreat
Weirs Beach
The price is ￥19,926
￥47,737 total
includes taxes & fees
May 10 - May 11
Weirs beach retreat
Table tennis

Stunning Lake Views close to Weirs Beach & Gunstock

Stunning Lake Views close to Weirs Beach & Gunstock
Weirs Beach
The price is ￥13,691
￥32,642 total
includes taxes & fees
May 6 - May 7
Stunning Lake Views close to Weirs Beach & Gunstock
Interior

Lakefront Salmon Cottage

Lakefront Salmon Cottage
Northwood
9.8 out of 10, Exceptional, (11 reviews)
"Awesome place for quite getaway."
United States
Jason L.
The price is ￥21,695
￥27,002 total
includes taxes & fees
Apr 30 - May 1
Lakefront Salmon Cottage
Exterior

Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is ￥15,797
￥34,245 total
includes taxes & fees
Apr 30 - May 1
Cedar Lodge Room 2 Queen Beds & Private Balcony
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

Homewood Suites by Hilton Dover

Homewood Suites by Hilton Dover

6/10 Okay
"Good parking"
Melissa 3-night trip
Posted 2 hours ago
Homewood Suites by Hilton Dover

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
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  • 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?

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock: This vacation home rental outside of Pittsfield is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

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?

Suncook River and Lily Lake 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 Pittsfield Town Hall and Josiah Carpenter Library.

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.