Pittsfield Vacation Rentals

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Vacation Rentals in Pittsfield

Postcard Cabins Blake Brook

2.0 star property
9.6 out of 10, Exceptional, (50)
"Perfect place "
The price is CA $177
CA $245 total
includes taxes & fees
Sep 2 - Sep 3
Postcard Cabins Blake Brook

Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi

10.0 out of 10, Exceptional, (13)
"We enjoyed our time so much. My dogs roamed around and everyone was so kind and the fire pit was fantastic."
The price is CA $157
CA $361 total
includes taxes & fees
Sep 2 - Sep 3
Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi

New Lakefront Home sleeps 14 with dock.

8.6 out of 10, Excellent, (65)
"Overall we enjoyed our stay. The house suited us just fine, no complaints. "
The price is CA $301
CA $716 total
includes taxes & fees
Sep 3 - Sep 4
New Lakefront Home sleeps 14 with dock.

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

9.8 out of 10, Exceptional, (175)
"Fantastic stay! The house was spotless, beautifully decorated, and had all the amenities we needed for a comfortable stay. The location was perfect—close to everything yet peaceful and relaxing. The host was responsive and made the check-in process seamless. Highly recommend and would definitely stay again!"
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

great location weirs beach area rental

9.4 out of 10, Exceptional, (24)
"The property was exactly as it was listed, The host was great"
The price is CA $493
CA $611 total
includes taxes & fees
Sep 2 - Sep 3
great location weirs beach area rental

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

8.6 out of 10, Excellent, (17)
"Nice location on the lake."
The price is CA $206
CA $425 total
includes taxes & fees
Sep 2 - Sep 3
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

A great cabin with lake views & access! Now Featuring AC/ Wi-Fi- & TV

9.2 out of 10, Wonderful, (11)
"Such a nice place to stay!"
The price is CA $140
CA $257 total
includes taxes & fees
Sep 3 - Sep 4
A great cabin with lake views & access! Now Featuring AC/ Wi-Fi- & TV

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

9.8 out of 10, Exceptional, (11)
"Great place, quiet and immaculate~!"
The price is CA $140
CA $257 total
includes taxes & fees
Sep 3 - Sep 4
Cabin for two with lake views & access Now featuring AC Wi-FI and TV

Secluded cozy Waterfront - Dams Beach

9.0 out of 10, Wonderful, (44)
"I came for Laconia bike week, and it was the perfect spot to be close to the action but also retreat when needed! Very relaxing and host was very accommodating!"
Secluded cozy Waterfront - Dams Beach

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

9.6 out of 10, Exceptional, (23)
"Loved the dock access and location. Easy check in and out !"
The price is CA $315
CA $606 total
includes taxes & fees
Sep 10 - Sep 11
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni.

9.4 out of 10, Exceptional, (140)
"Everything was clean & convenient. Such a beautiful beach also! "
Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni.

Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

9.0 out of 10, Wonderful, (21)
"Excellent"
The price is CA $177
CA $385 total
includes taxes & fees
Sep 2 - Sep 3
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

Cozy Cottage 2 Bedroom With Amazing View <br>

10.0 out of 10, Exceptional, (26)
"This place was just as described and just what our little group was looking for. It was clean and convenient to all the main attractions of Lake Winnepesaki. "
Cozy Cottage 2 Bedroom With Amazing View <br>

The Ultimate Getaway at a Charming Two-Bedroom Lakeside Cottage on Winnipesaukee

10.0 out of 10, Exceptional, (15)
"Great cottage right by the lake. Host was incredibly responsive and helpful. Fun back yard for games and grilling. 5/5 would recommend a stay here!"
The Ultimate Getaway at a Charming Two-Bedroom Lakeside Cottage on Winnipesaukee

Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3

9.0 out of 10, Wonderful, (11)
"Cabin was clean, beds were comfortable, kitchenette was well stocked. Outside sitting and firepits were an added bonus. Bicycles available, kayaking available albeit a little small in size. A little difficult to get into the water."
The price is CA $157
CA $320 total
includes taxes & fees
Sep 2 - Sep 3
Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3

Cottage with Lake Views & Access Now featuring AC Wi-FI and TV

9.6 out of 10, Exceptional, (10)
"Everything was great!"
The price is CA $140
CA $260 total
includes taxes & fees
Sep 3 - Sep 4
Cottage with Lake Views & Access Now featuring AC Wi-FI and TV

🌟 Lakefront Bliss Awaits – Your Ultimate Getaway! 🏡🌊⛰️

9.4 out of 10, Exceptional, (27)
"Our group of 8 enjoyed the spacious house and proximity to the lake. The no contact check in was great. "
🌟 Lakefront Bliss Awaits – Your Ultimate Getaway! 🏡🌊⛰️

Come & enjoy beautiful Lake Winni! Concerts are within 5 min. Economy pricing

9.8 out of 10, Exceptional, (13)
"Great place to stay. Was the perfect spot to git the white mountains/conway. While also being super close to the pavilion to take in a concert. Would definitely stay here again/recommend!"
Come & enjoy beautiful Lake Winni! Concerts are within 5 min. Economy pricing

On Lake Winnipesaukee!,Year round house, private beach and great yard

8.8 out of 10, Excellent, (33)
"We had a great stay, great little beach area for young kids, a dock to moor a rented boat, huge lawn, beautiful sunsets, just a wonderful spot!"
On Lake Winnipesaukee!,Year round house, private beach and great yard

Lake view condo, Private Beach, Private concert entrance, pool

9.8 out of 10, Exceptional, (17)
"If you are going to a show at the BONH pavillion you cannot beat this place. Private Beach and you can walk to the show. It's just a few hundred yards. "
The price is CA $158
CA $365 total
includes taxes & fees
Sep 29 - Sep 30
Lake view condo, Private Beach, Private concert entrance, pool
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

Find out more about Pittsfield

Everything you need to know about Pittsfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pittsfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield vacation rentals we have selected for you start as low as CA $140 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

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 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.