A calm lake reflecting colorful autumn trees and misty mountains in the distance.

Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Pittsfield vacation rentals

View from property

1. Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
2.5 star property
Epsom
9.6 out of 10, Exceptional, (181 reviews)
"Beautiful place love it all!!!"
United States
Emelin
$175 nightly
The price is $190
Sep 8 - Sep 9
Total with taxes and fees
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Lake

2. The Cottages at Harvey Lake

The Cottages at Harvey Lake
3.0 star property
Northwood
8.8 out of 10, Excellent, (47 reviews)
"The view of the lake from the cabin was excellent. "
United States
Matt
$148 nightly
The price is $161
Sep 8 - Sep 9
Total with taxes and fees
The Cottages at Harvey Lake
Interior

3. Lakefront Salmon Cottage

Lakefront Salmon Cottage
Northwood
9.8 out of 10, Exceptional, (16 reviews)
"Awesome place for quite getaway."
United States
Jason L.
$168 nightly
The price is $183
Sep 8 - Sep 9
Total with taxes and fees
Lakefront Salmon Cottage
Exterior

4. Lakefront Purple Cottage

Lakefront Purple Cottage
Northwood
9.2 out of 10, Wonderful, (7 reviews)
"Quaint colorful just right ."
United States
Susan B.
$174 nightly
The price is $189
Aug 11 - Aug 12
Total with taxes and fees
Lakefront Purple Cottage
Dining

5. Lakefront Yellow Cottage

Lakefront Yellow Cottage
Northwood
9.4 out of 10, Exceptional, (6 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.
$189 nightly
The price is $205
Sep 1 - Sep 2
Total with taxes and fees
Lakefront Yellow Cottage
Outdoor dining

6. Lakefront Secluded Cottage in Northwood, New Hampshire

Lakefront Secluded Cottage in Northwood, New Hampshire
Northwood
$180 nightly
The price is $196
Sep 8 - Sep 9
Total with taxes and fees
Lakefront Secluded Cottage in Northwood, New Hampshire
Marina

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

Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3
Alton
8.8 out of 10, Excellent, (13 reviews)
"Nicely kept enjoyable stay"
United States
Shirley G.
$209 nightly
The price is $228
Sep 2 - Sep 3
Total with taxes and fees
Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3
Sun loungers

8. Lakes Region Cozy Camp in Shellcamp

Lakes Region Cozy Camp in Shellcamp
Gilmanton
9.8 out of 10, Exceptional, (27 reviews)
"Excellent and Know host. Great view. Very clean."
United States
Jonathan
$332 nightly
The price is $360
Aug 10 - Aug 11
Total with taxes and fees
Lakes Region Cozy Camp in Shellcamp
Interior

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

Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Alton
10.0 out of 10, Exceptional, (1 review)
"This is a classic old-style cabin that reminded us of our childhood family trips in the 60’s. It’s not new, but a heck of a lot of fun if you’re in the right head space. Easily walked to town for dinner and to the shore. Clean and had everything we needed."
United States
Christine F.
$216 nightly
The price is $235
Sep 1 - Sep 2
Total with taxes and fees
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Outdoor dining

10. 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.
$281 nightly
The price is $305
Sep 8 - Sep 9
Total with taxes and fees
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Exterior

11. Lakefront Orange Cottage

Lakefront Orange Cottage
Northwood
9.0 out of 10, Wonderful, (12 reviews)
"The personal touch and welcome gift was lovely z"
United States
Joyce
$166 nightly
The price is $180
Aug 19 - Aug 20
Total with taxes and fees
Lakefront Orange Cottage
Interior

12. Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit

Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Gilmanton
9.8 out of 10, Exceptional, (37 reviews)
"Lovely stay in a quiet area. The hot tub was great to unwind in after hiking in the area!"
United States
Cristofer V.
$352 nightly
The price is $382
Sep 2 - Sep 3
Total with taxes and fees
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Interior

13. Lakefront Green Cottage

Lakefront Green Cottage
Northwood
10.0 out of 10, Exceptional, (6 reviews)
"Great place. "
United States
Joseph G.
$174 nightly
The price is $189
Aug 18 - Aug 19
Total with taxes and fees
Lakefront Green Cottage
Smart TV, books

14. New, Clean, Downtown Getaway!

New, Clean, Downtown Getaway!
Concord
9.6 out of 10, Exceptional, (10 reviews)
"Perfect location, nice and clean as well"
United States
Derek T.
$161 nightly
The price is $175
Aug 12 - Aug 13
Total with taxes and fees
New, Clean, Downtown Getaway!
Private kitchen

15. Cozy Cottage on a Lake, near Gunstock Mountain

Cozy Cottage on a Lake, near Gunstock Mountain
Gilmanton
8.8 out of 10, Excellent, (5 reviews)
"We had a wonderful time during our stay. The cottage was in a great location, exactly as advertised, and spotlessly clean. The hot tub was great. Can’t think of a single thing we’d change. Would love to come back again during the summer months."
United States
Dawn P.
$362 nightly
The price is $393
Sep 8 - Sep 9
Total with taxes and fees
Cozy Cottage on a Lake, near Gunstock Mountain
TV

16. 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.
$366 nightly
The price is $399
Sep 8 - Sep 9
Total with taxes and fees
Newly Renovated Cottage 4 in Alton Bay, NH
Property grounds

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

Cozy hotel-style suite right on the water, shared patio, free WiFi
Alton
9.0 out of 10, Wonderful, (19 reviews)
"One of our favorite places to stay in this area."
United States
Anthony G.
$281 nightly
The price is $305
Sep 8 - Sep 9
Total with taxes and fees
Cozy hotel-style suite right on the water, shared patio, free WiFi
House (2 Bedrooms) | Interior

18. 7 Mi to Hiking: Waterfront Long Pond Gem!

7 Mi to Hiking: Waterfront Long Pond Gem!
3.0 star property
Barrington
10.0 out of 10, Exceptional, (1 review)
"Well designed and maintained property. We enjoyed the little touches like the automatic nightlights and heater in bathroom. Wish we could have spent more time here but we attended the Deerfield fair. Highly recommended. "
United States
Ronald
$523 nightly
The price is $568
Aug 9 - Aug 10
Total with taxes and fees
7 Mi to Hiking: Waterfront Long Pond Gem!
Exterior

19. 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, (19 reviews)
"Nice location on the lake."
United States
Mary L.
$308 nightly
The price is $334
Sep 8 - Sep 9
Total with taxes and fees
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
TV, books

20. On Baxter Lake: Wooded Retreat Near Trails

On Baxter Lake: Wooded Retreat Near Trails
Farmington
10.0 out of 10, Exceptional, (3 reviews)
"What a beautiful and cozy little property! We really enjoyed our stay."
United States
Rebekah
$416 nightly
The price is $451
Aug 23 - Aug 24
Total with taxes and fees
On Baxter Lake: Wooded Retreat Near Trails
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

Fireside Inn & Suites Gilford

Fireside Inn & Suites Gilford

8/10 Good
"Very friendly staff, clean rooms great location"
Nikki 2-night trip
Posted 3 hours ago
Fireside Inn & Suites Gilford

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Pittsfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $190 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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 Bliss Awaits – Your Ultimate Getaway! 🏡🌊⛰️: This vacation home rental outside of Pittsfield is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the hot tub in this rental home to help you unwind.

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.