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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 105 Cottages in Pittsfield with updated reviews, rates, and availability.

Cozy, Pet-Friendly Escape Near Lake & Mountains
Property grounds

Cozy, Pet-Friendly Escape Near Lake & Mountains

10.0 out of 10, Exceptional, (28)
"The property was very nice and clean. We enjoyed our stay very much!"
The price is AED 551
AED 1,566 total
includes taxes & fees
16 Mar - 17 Mar
Cozy, Pet-Friendly Escape Near Lake & Mountains
Lakefront Winnisquam Cottage with dock & boat ramp
Exterior

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
Charming dog-friendly lakefront cottage with private dock & community beach

Charming dog-friendly lakefront cottage with private dock & community beach

8.8 out of 10, Excellent, (5)
"Great spot, great doc, great everything. It was a little small. but still nice. The only thing that it lacked was a couple of AC units because it gets very hot if it is a hot humid day especially upstairs in the loft."
Charming dog-friendly lakefront cottage with private dock & community beach
Waterfront Cottage, Quiet and Secluded, on Swains Lake
The cottage and large screen porch and Weber 22" charcoal grill

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
Adorable cottage with a full kitchen, gas fireplace, pool, koi pond, & gazebo

Adorable cottage with a full kitchen, gas fireplace, pool, koi pond, & gazebo

8.8 out of 10, Excellent, (9)
"Enjoyed very much! Very cozy."
Adorable cottage with a full kitchen, gas fireplace, pool, koi pond, & gazebo
Lakefront home with a deck, gas grill, WiFi, dock & golf nearby

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
cutie Lakefront Cottage with private beach
Outdoor seating area.

cutie Lakefront Cottage with private beach

10.0 out of 10, Exceptional, (3)
"Weather was great"
cutie Lakefront Cottage with private beach
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Bathroom

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 525
AED 650 total
includes taxes & fees
2 Mar - 3 Mar
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Charming 3 bedroom Cottage, waterfront with boat slip
A nice open concept for you to engage with all the guests.

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
Walk to Marina: Cute Gilford Cottage w/ Grill
Gilford Vacation Rental | 1BR | 1.5BA | Step-Free Entry w/ Ramp | 700 Sq Ft

Walk to Marina: Cute Gilford Cottage w/ Grill

9.8 out of 10, Exceptional, (17)
"Older but updated 1 bedroom cottage. Owners extremely helpful."
Walk to Marina: Cute Gilford Cottage w/ Grill
Paugus Bay Cottage waterfront cottage on private island! Walk to Paugus Bay Pub!
Living area

Paugus Bay Cottage waterfront cottage on private island! Walk to Paugus Bay Pub!

10.0 out of 10, Exceptional, (2)
"Wonderful charming waterfront cottage with all amenities including fun gameroom. It includes a nice clean shared beach in gated community. The owner was easily accessible and answered questions promptly. Highly recommended for peaceful lake front retreat."
Paugus Bay Cottage waterfront cottage on private island! Walk to Paugus Bay Pub!
Cozy Cottage 2 Bedroom With Amazing View <br>
Water view sitting area

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

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

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 988
AED 1,558 total
includes taxes & fees
25 Feb - 26 Feb
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
1 Bedroom with private courtyard

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

9.6 out of 10, Exceptional, (7)
"I just needed some rest and that's what I got. "
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
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.
Welcome to the Lake
Mi Casa Su Casa

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
Summer Breeze on Lake Winnisquam. Pet Friendly!
Sit Lakeside and enjoy the amazing view

Summer Breeze on Lake Winnisquam. Pet Friendly!

9.0 out of 10, Wonderful, (2)
"I grew up in land of 10,100 lakes (MN) and found this to be very similar. We loved the location, property and retro style. It brought back many memories of the 60's. The check-in went well, but not the way most VRBOs inform you. Now I know. I expected info to be pushed to me, but the process was slightly different. I recommend!"
Summer Breeze on Lake Winnisquam. Pet Friendly!
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
9.6 out of 10, Exceptional, (4)
"Amamos a experiência,local limpo e aconchegante "
The price is AED 331
AED 359 total
includes taxes & fees
3 Mar - 4 Mar
Postcard Cabins Blake Brook
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock
Interior

Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock

9.8 out of 10, Exceptional, (93)
"Had an amazing stay. Cabin was exactly as described and host was excellent in communicating and making sure we had everything we needed (including snow removal etc) Would stay again!!"
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock
Cozy, Pet-Friendly Escape Near Lake & Mountains
Property grounds

Cozy, Pet-Friendly Escape Near Lake & Mountains

10.0 out of 10, Exceptional, (28)
"The property was very nice and clean. We enjoyed our stay very much!"
The price is AED 551
AED 1,566 total
includes taxes & fees
16 Mar - 17 Mar
Cozy, Pet-Friendly Escape Near Lake & Mountains
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 525 and AED 988 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.