Search Cottages in Pittsfield

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Cottages in Pittsfield

Rustic Rose Cottage of Historic West Lebanon
10.0 out of 10, Exceptional, (23)
"Beautiful, easy access, well appointed"
United States
Jeffrey J.
The price is AED 474
AED 925 total
includes taxes & fees
10 Nov - 11 Nov
Rustic Rose Cottage of Historic West Lebanon
On Baxter Lake: Wooded Retreat Near Trails
3.0 star property
On Baxter Lake: Wooded Retreat Near Trails
Newly Renovated Cottage 6
10.0 out of 10, Exceptional, (3)
"Great location, and amenities, including the game room, pool and bikes. Hosts were very responsive and accomodating. "
United States
Vanessa
The price is AED 415
AED 856 total
includes taxes & fees
25 Oct - 26 Oct
Newly Renovated Cottage 6
Newly Renovated Cottage 4 in Alton Bay, NH
9.0 out of 10, Wonderful, (4)
"Game room fun for all ages. "
United States
Anonymous traveler
The price is AED 419
AED 1,324 total
includes taxes & fees
24 Oct - 25 Oct
Newly Renovated Cottage 4 in Alton Bay, NH
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
8.6 out of 10, Excellent, (18)
"Nice location on the lake."
United States
Mary L.
The price is AED 551
AED 1,141 total
includes taxes & fees
26 Oct - 27 Oct
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
10.0 out of 10, Exceptional, (4)
"We had a perfect stay. Super cute cabin, clean and very comfortable.We thoroughly enjoyed or time there. Very easy process and would absolutely recommend and book again."
United States
Jessica G.
The price is AED 818
AED 1,003 total
includes taxes & fees
24 Oct - 25 Oct
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
9.6 out of 10, Exceptional, (10)
"Great property. Loved our stay and the owners were great! Definitely will book again "
United States
Marcus
The price is AED 744
AED 915 total
includes taxes & fees
28 Oct - 29 Oct
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Newly Renovated Cottage on Main Street Alton Bay #5
10.0 out of 10, Exceptional, (1)
"Great places. Quiet and quaint and close to the lake and restaurants. Will rent again "
United States
Brian B.
The price is AED 419
AED 880 total
includes taxes & fees
26 Oct - 27 Oct
Newly Renovated Cottage on Main Street Alton Bay #5
Newly Renovated Cottage 7 in Alton Bay
10.0 out of 10, Exceptional, (1)
"endroit magnifique,emplacement agréable avec commodité sur place et près du lac et restaurant."
Canada
Alexandra R.
The price is AED 441
AED 916 total
includes taxes & fees
26 Oct - 27 Oct
Newly Renovated Cottage 7 in Alton Bay
Newly Renovated Cottage 3 on Main Street Alton Bay!
10.0 out of 10, Exceptional, (1)
"Great little spot right next to the bay. Team was super responsive prior, during and after check in. Would highly recommend. "
United States
Andy S.
The price is AED 415
AED 860 total
includes taxes & fees
25 Oct - 26 Oct
Newly Renovated Cottage 3 on Main Street Alton Bay!
Newly Renovated Cottage 8 Main Street Alton Bay!
7.0 out of 10, Good, (2)
" Both bedroom doors don’t close properly, which affects privacy. There’s also no mirror in the bathroom and nowhere to hang clothes, either in the bathroom or closet. The space is really best suited for two adults — our third guest had trouble sleeping comfortably. Overall, we felt the value didn’t quite match the price and description."
United States
Pedram S.
The price is AED 459
AED 1,024 total
includes taxes & fees
27 Oct - 28 Oct
Newly Renovated Cottage 8 Main Street Alton Bay!
Hiking & Snowmobile Trails On-site: Alton Retreat!
3.0 star property
The price is AED 338
AED 748 total
includes taxes & fees
4 Nov - 5 Nov
Hiking & Snowmobile Trails On-site: Alton Retreat!
Charming Alton Bay Getaway – 1BR Cottage, Pool Access & Walk to Lake
The price is AED 459
AED 904 total
includes taxes & fees
25 Oct - 26 Oct
Charming Alton Bay Getaway – 1BR Cottage, Pool Access & Walk to Lake
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
10.0 out of 10, Exceptional, (4)
"Great location & comfortable! "
United States
Jeanine L.
The price is AED 669
AED 826 total
includes taxes & fees
28 Oct - 29 Oct
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
10.0 out of 10, Exceptional, (4)
"It was very cute and clean, loved the outside area and would def be back again."
United States
Anais & Zach
The price is AED 744
AED 915 total
includes taxes & fees
24 Oct - 25 Oct
Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
10.0 out of 10, Exceptional, (16)
"I love and have had a couple decades of Lake Winnepesaukee summers. With my boys now grown and raising their own families in other parts of the country, I drove up for a couple days, by myself, for a Lake Winni fix. The on site cottage was perfect in terms of location, privacy, cleanliness and the unspoken presence of security that was important to me a line traveler. I highly recommend this Inn for a special week on the lake, couples, small families. Accommodations are beautifully updated and...
United States
Lisa B.
The price is AED 818
AED 1,003 total
includes taxes & fees
26 Oct - 27 Oct
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard
10.0 out of 10, Exceptional, (5)
"Booked a last minute trip with the family and it was perfect. Right near downtown and a cozy place to rest with the kids."
United States
Sean P.
The price is AED 798
AED 982 total
includes taxes & fees
24 Oct - 25 Oct
Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard
Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
10.0 out of 10, Exceptional, (4)
"Everything was great!"
United States
Leah F.
The price is AED 1,145
AED 1,402 total
includes taxes & fees
24 Oct - 25 Oct
Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
Cottage 1-2 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
10.0 out of 10, Exceptional, (2)
"In addition to everything this property offers we found there was a nearby 12mile bike trail that goes through the woods passing lakes on the the route, and bikes were available at the property."
United States
Justin
The price is AED 987
AED 1,202 total
includes taxes & fees
27 Oct - 28 Oct
Cottage 1-2 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
Cozy Cottage on a Lake, near Gunstock Mountain
9.0 out of 10, Wonderful, (2)
"We had a great time. Loved the cabin super cute. Neighborhood & neighbors very nice. The lake & private beaches were great. We enjoyed the hot tub & fire pit. I brought a few games, but you had a nice selection as well. Kitchen was very nice with everything we needed for some nice big breakfasts to start our day. We did run into a bit of a problem with the water running out. During showers, but we worked through it. Over all it was a great place. Thank you. Kim, Steve,Brianna,Cam & Brody "
United States
kim M.
The price is AED 628
AED 1,455 total
includes taxes & fees
27 Oct - 28 Oct
Cozy Cottage on a Lake, near Gunstock Mountain
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pittsfield Hotel Reviews

Frequently asked questions

Why book your cottage in Pittsfield with Expedia?
Reserving a cottage in Pittsfield is as easy as working out your travel dates and selecting your ideal place for a getaway in nature. From upmarket retreats to affordable properties and cottages that feature amenities like laundry facilities, Expedia has something for all tastes. As for awesome deals? We've got your back!
How can I find cheap cottages in Pittsfield?
Expedia can help you track down cheap cottages in Pittsfield. To discover a superb stay in just a few keystrokes, use our convenient filter tool to tailor your search results by star rating, budget and amenities.