Pittsfield Vacation Rentals

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Our top choices for Pittsfield vacation rentals

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 CA $216
CA $265 total
includes taxes & fees
Jun 1 - Jun 2
The Barn - Lake View and Pet Friendly

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, (151 reviews)
"Great stay "
United States
Edward
The price is CA $191
CA $267 total
includes taxes & fees
May 27 - May 28
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

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 CA $158
CA $331 total
includes taxes & fees
May 20 - May 21
Newly Renovated Cottage 7 in Alton Bay

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 CA $140
CA $258 total
includes taxes & fees
May 20 - May 21
Cabin for two with lake views & access Now featuring AC Wi-FI and 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 CA $190
CA $533 total
includes taxes & fees
May 27 - May 28
Newly Renovated Cottage 4 in Alton Bay, NH

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 CA $187
CA $232 total
includes taxes & fees
May 21 - May 22
Lakefront Salmon Cottage

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Alton
8.6 out of 10, Excellent, (18 reviews)
"Nice location on the lake."
United States
Mary L.
The price is CA $206
CA $439 total
includes taxes & fees
May 20 - May 21
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

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 CA $169
CA $355 total
includes taxes & fees
May 27 - May 28
Rustic Rose Cottage of Historic West Lebanon

Lakefront Orange Cottage

Lakefront Orange Cottage
Northwood
9.0 out of 10, Wonderful, (11 reviews)
"Location was nice right in front of the lake and we took advantage of the kayaks. Shower was very small and cottage a bit rustic but for the location and price was great. "
United States
Danna P.
The price is CA $211
CA $229 total
includes taxes & fees
May 21 - May 22
Lakefront Orange Cottage

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)
"Excellent stay"
United States
Kara
The price is CA $204
CA $252 total
includes taxes & fees
May 26 - May 27
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

Lakefront Purple Cottage

Lakefront Purple Cottage
Northwood
9.2 out of 10, Wonderful, (7 reviews)
"Quaint colorful just right ."
United States
Susan B.
The price is CA $228
CA $280 total
includes taxes & fees
May 20 - May 21
Lakefront Purple Cottage

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 CA $187
CA $203 total
includes taxes & fees
May 21 - May 22
The Cottages at Harvey Lake

Lakefront Yellow Cottage

Lakefront Yellow Cottage
Northwood
10.0 out of 10, Exceptional, (5 reviews)
"Clean, friendly, a great place to stay. I kayaked in the lake and it was beautiful. Hope to stay again next summer!"
United States
Ravaioli N.
The price is CA $228
CA $280 total
includes taxes & fees
May 20 - May 21
Lakefront Yellow Cottage

Cabin in the Woods

Cabin in the Woods
Franklin
9.8 out of 10, Exceptional, (6 reviews)
"Great cozy cabin! Terrific fire pit and nice wood grain"
United States
Tyler P.
The price is CA $231
CA $326 total
includes taxes & fees
May 20 - May 21
Cabin in the Woods

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 CA $177
CA $400 total
includes taxes & fees
May 20 - May 21
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

Stunning Lake Views close to Weirs Beach & Gunstock

Stunning Lake Views close to Weirs Beach & Gunstock
Weirs Beach
The price is CA $131
CA $296 total
includes taxes & fees
May 20 - May 21
Stunning Lake Views close to Weirs Beach & Gunstock

Gunstock Chalet - Close to Gunstock, BNH Pavilion Concerts, and Lake Winni

Gunstock Chalet - Close to Gunstock, BNH Pavilion Concerts, and Lake Winni
Gilford
The price is CA $316
CA $729 total
includes taxes & fees
May 20 - May 21
Gunstock Chalet - Close to Gunstock, BNH Pavilion Concerts, and Lake Winni

9 Lake Street

9 Lake Street
3.0 star property
Wolfeboro
10.0 out of 10, Exceptional, (1 review)
"Great location and wonderful space! Will definitely stay again"
United States
Roog
The price is CA $224
CA $370 total
includes taxes & fees
May 27 - May 28
9 Lake Street

Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath

Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (5 reviews)
"It was very cute and clean, loved the outside area and would def be back again."
United States
Anais & Zach
The price is CA $191
CA $237 total
includes taxes & fees
May 20 - May 21
Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath

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, (24 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 CA $339
CA $557 total
includes taxes & fees
May 26 - May 27
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pittsfield. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.