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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
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25 Apr - 27 Apr
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23 May - 25 May

Compare 120 Cottages in Pittsfield with updated reviews, rates, and availability.

Cozy, Pet-Friendly Escape Near Lake & Mountains
Miscellaneous

Cozy, Pet-Friendly Escape Near Lake & Mountains

10.0 out of 10, Exceptional, (30)
"Charming, clean and lovely place to stay. Owners were very easy to communicate with. Place was gorgeous. We had a great time. We would definitely stay here again and highly recommend it!!! "
Cozy, Pet-Friendly Escape Near Lake & Mountains
Lakefront Winnisquam Cottage with dock & boat ramp
Smart TV, DVD player, books, video library

Lakefront Winnisquam Cottage with dock & boat ramp

10.0 out of 10, Exceptional, (33)
"Karen and John were amazing hosts! The house was just perfect for our little family and small dog. We were greeted with fun activity books, sidewalk chalk and bubbles for my daughter… a bottle of wine, fire wood, fixings for s’mores and even a new toy for my dog! They were attentive, available when we needed them and so very kind to me and my family. The kayaks and water toys kept my daughter entertained for hours. We were able to bring our boat and had our own dock space for the entire time...
Lakefront Winnisquam Cottage with dock & boat ramp
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (24)
"Awesome place for a getaway. The cottage is fully stocked and has everything you could need. The hot tub is especially nice and is in tip top shape. Loved being in the hot tub and watching the stars. Enjoyed the fire pit! Barbequed on the grill and ate dinner on the porch .porch. Kitchen was easy to cook ineverything. "
The price is AED 555
AED 1,004 total
includes taxes & fees
21 Apr - 22 Apr
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Winnipesaukee house w/ dock included.
Exterior

Winnipesaukee house w/ dock included.

8.8 out of 10, Excellent, (3)
"Love Laconia, and this is a lovely little place. "
Winnipesaukee house w/ dock included.
Rustic cottage on the water - private and pet friendly!

Rustic cottage on the water - private and pet friendly!

9.8 out of 10, Exceptional, (36)
"It was very secluded, quiet, long dirt road. We enjoyed it very much, clean, but could use some udated furniture and supplies. The river is beautiful, and enjoyed fishing. The hosts are very nice people, friendly and accommodatting!!!!"
Rustic cottage on the water - private and pet friendly!
Waterfront Cottage, Quiet and Secluded, on Swains Lake
Miscellaneous

Waterfront Cottage, Quiet and Secluded, on Swains Lake

9.4 out of 10, Exceptional, (62)
"Lovely stay,everything amazing would highly recommend!"
Waterfront Cottage, Quiet and Secluded, on Swains Lake
Lakefront home with a deck, gas grill, WiFi, dock & golf nearby
View from property

Lakefront home with a deck, gas grill, WiFi, dock & golf nearby

9.4 out of 10, Exceptional, (3)
"The property is beautiful and beyond our expectations. The owner has everything you might need. Plenty of towels. Clean linens. The view was outstanding! The neighbor was awesome and helped us out tremendously. The check in was horrible with Vacasa. Not the property owners fault. After driving 14 hours and arriving late in the evening (7:00 pm) the keys were not in the lockbox. Then after contacting Vacasa, we did not receive keys to the property until after 9:00. Once we received the keys...
Lakefront home with a deck, gas grill, WiFi, dock & golf nearby
LAKE FRONT!! SKI ALL WINTER!!!
Property grounds

LAKE FRONT!! SKI ALL WINTER!!!

9.2 out of 10, Wonderful, (105)
"This place was perfect for our weekend stay with our 3 small dogs. We loved the beautiful lake view, the large deck with bbq and the firepit in the front yard. It is so hard to find a nice place that will allow us to bring our 3 small dogs. Peter was very friendly and accommodating and answered all our questions promptly. We would definitely stay here again."
LAKE FRONT!! SKI ALL WINTER!!!
Cottage with great beach.
Property grounds

Cottage with great beach.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Three of us just needed a place to stay while we visited the area. This place was perfect for what we needed. It's not large but all we were looking for was a place to sleep. "
Cottage with great beach.
Walk to Marina: Cute Gilford Cottage w/ Grill
Fridge, microwave, stovetop, coffee/tea maker

Walk to Marina: Cute Gilford Cottage w/ Grill

9.8 out of 10, Exceptional, (17)
"Very happy with our stay we we're ice fishing in the Merridith derby and this was a perfect location. Drive right out on the ice with the truck and the cottage had great heat and awesome hot water shower. Will be back"
Walk to Marina: Cute Gilford Cottage w/ Grill
Fun Family Wolfeboro Winnipesaukee Bay Waterfront with SUP, 5 Kayaks & 2 Canoes
Property grounds

Fun Family Wolfeboro Winnipesaukee Bay Waterfront with SUP, 5 Kayaks & 2 Canoes

9.6 out of 10, Exceptional, (84)
"Quick walk to downt"
Fun Family Wolfeboro Winnipesaukee Bay Waterfront with SUP, 5 Kayaks & 2 Canoes
cutie Lakefront Cottage with private beach
Property grounds

cutie Lakefront Cottage with private beach

10.0 out of 10, Exceptional, (3)
"Weather was great"
cutie Lakefront Cottage with private beach
Charming 3 bedroom Cottage, waterfront with boat slip
TV, fireplace, books

Charming 3 bedroom Cottage, waterfront with boat slip

10.0 out of 10, Exceptional, (4)
"We had an amazing stay, the property was gorgeous, had all the amenities we needed. Communication with owners was wonderful. Felt like a home away from home. "
Charming 3 bedroom Cottage, waterfront with boat slip
The Ultimate Getaway at a Charming Two-Bedroom Lakeside Cottage on Winnipesaukee
Marina

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

10.0 out of 10, Exceptional, (7)
"My boyfriend and I were looking for a quiet getaway to enjoy some time together. This cottage was absolutely perfect for some quiet time together! Nick and Tayla were very kind and accommodating, giving us recommendations on places to go and things to see! We can't wait to come back! "
The Ultimate Getaway at a Charming Two-Bedroom Lakeside Cottage on Winnipesaukee
Alton Bay 2 Bed Room Cottage with Dock
Miscellaneous

Alton Bay 2 Bed Room Cottage with Dock

10.0 out of 10, Exceptional, (14)
"Can’t say enough about the property grounds and cabin 5! Super clean, comfy, pool, grill, fire pit, great access to lake with boat slip and all that Alton Bay has to offer. Highly recommend. Thank you Jill and family!"
Alton Bay 2 Bed Room Cottage with Dock
Cozy Cottage 2 Bedroom With Amazing View <br>
Interior

Cozy Cottage 2 Bedroom With Amazing View <br>

10.0 out of 10, Exceptional, (24)
"The Cozy Cottage nestled in the heart of Alton Bay, NH was just what my family of four needed for an extended holiday weekend getaway. My favorite keepsake from staying at Rich’s Cozy Cottage was most definitely the spectacular view and the live music heard from across the Bay while I relaxed on the comfy blue chairs in the large breezeway! We even brought our pugs and our 22 ft boat. Next time I hope to be able to reserve a dock, but the ramp is literally a five minute walk away."
Cozy Cottage 2 Bedroom With Amazing View <br>
Rustic cottage in private location - Pet friendly!
View from property

Rustic cottage in private location - Pet friendly!

9.8 out of 10, Exceptional, (97)
"The cottage was as described and shown in the listing. On our first day we had issues with heat (both hot water and heating) but John was more than accommodating and had us shifted to another cottage immediately and he in fact bought us lunch for the inconvenience (thank you John!). Our second day of stay was perfect without issues. They have a private beach with boats which you can use. I would recommend booking with them directly."
Rustic cottage in private location - Pet friendly!
Welcome to the Lake
Terrace/patio

Welcome to the Lake

10.0 out of 10, Exceptional, (35)
"The lake is right outside the door, and the view from the living room is just beautiful! We were in the area for work and didn't have much time to enjoy it, but there is a gorgeous gazebo on the side and a fire pit on the patio out back - both looking directly our onto the lake. One small downside, the bedroom is quite small - but we did enjoy the view of the sunrise on the lake right from the bed.."
Welcome to the Lake
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Beach nearby

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

10.0 out of 10, Exceptional, (12)
"Very nice spot nice get away would stay there again"
The price is AED 692
AED 855 total
includes taxes & fees
31 Mar - 1 Apr
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Little Loon Cottage and Beach on Webster Lake
Terrace/patio

Little Loon Cottage and Beach on Webster Lake

10.0 out of 10, Exceptional, (2)
"Property is exactly how it's described. Had a short stay in the fall. Wish we'd had time to enjoy the water."
Little Loon Cottage and Beach on Webster Lake
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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Other property types in Pittsfield

Postcard Cabins Blake Brook
Exterior

Postcard Cabins Blake Brook

2.0 star property
9.8 out of 10, Exceptional, (10)
"Wondering. Had a great time"
The price is AED 496
AED 538 total
includes taxes & fees
7 Apr - 8 Apr
Postcard Cabins Blake Brook
Lake Access, Mtn Views, Game Room, Hot Tub & More!
Miscellaneous

Lake Access, Mtn Views, Game Room, Hot Tub & More!

Lake Access, Mtn Views, Game Room, Hot Tub & More!
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Indoor pool

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

10.0 out of 10, Exceptional, (167)
"Massive 7,000 sq ft. super cool house close to Gunstock that felt like we rented an entire commercial lodge. Bedrooms and baths for everyone, large indoor pool, hot tub, steam and sauna, bar area, game room, and huge fireplaced dining room with seating for 20! Kids were ecstatic and we had the best time. Clean, responsive and pleasant owner as well. If you have a large family, this is the place...you won't be disappointed!PatrickMarshfield, MA"
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
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.

Frequently asked questions

How much do cottages in Pittsfield cost?
Prepare to pay between AED 555 and AED 692 per night for cottages in Pittsfield. Whatever your budget, an excellent stay is just a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Pittsfield with Expedia?
Expedia has some excellent cottages in Pittsfield, so get set for a memorable vacay close to nature. If you need to stick to a budget, choose how much you’d like to spend and the preferred star rating of your property. Or, make the most of our filters to search for cottages with free WiFi or a pool. We’ll help you find the right place whatever your style of travel or plans.
How can I find cheap cottages in Pittsfield?
With Expedia’s user-friendly filter tool, booking cheap cottages in Pittsfield is a breeze. To find accommodations that’ll make your hip pocket happy, refine your search by budget, star rating and amenities.