Photo by Linda Barreira

Search Cottages in Windham

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare Cottages in Windham with updated reviews, rates, and availability.

Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself
10.0 out of 10, Exceptional, (11)
"Very quite and peaceful"
Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself
Cozy Waterfront Cottage!!
Cozy Waterfront Cottage!!
The Cozy Cottage
The Cozy Cottage
Save an average of 15% on thousands of hotels when you're signed in
Cozy country tiny house
8.0 out of 10, Very Good, (1)
"Quiet and cozy.. great for a get away weekend"
Cozy country tiny house
The PondeRosa cottage at Cobbett's pond
10.0 out of 10, Exceptional, (10)
"The weekend that my girlfriend and I spent here was fantastic. Ana was very helpful and the cottage was beautiful and cozy. Hiking trails, food, bars, and stores all in 10 minutes or less driving range. Would easily stay here again, nothing negative to say at all!"
The PondeRosa cottage at Cobbett's pond
Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!
10.0 out of 10, Exceptional, (8)
"A short walk to the lake where we enjoyed kayaking and were the first to use the new firepit. Great location with all the amenities you would need."
Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!
Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.
10.0 out of 10, Exceptional, (2)
"Third time staying here we love everything the place has to offer. It’s great for my family. Also can’t beat the location."
Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.
Pet-friendly Merrimack Home w/ Grill: 8 Mi to Mall
3.0 star property
Pet-friendly Merrimack Home w/ Grill: 8 Mi to Mall
Cozy 3 bedroom seasonal cottage with very short walk to private community beach
9.8 out of 10, Exceptional, (7)
"This house has a big kitchen/living room and comfy beds. Not drinking the well water was odd-would be nice if the water provided was in glass and more plentiful. Also the paddle board was broken which was a bummer but the owner was very responsive and worked with us to make up for that. It’s a sweet cottage."
Cozy 3 bedroom seasonal cottage with very short walk to private community beach
Riverfront New Hampshire Cottage w/ Boat Dock
3.0 star property
Riverfront New Hampshire Cottage w/ Boat Dock
Clean Cottage w/Heated Pools - Hot Tub - Playground - Golf Cart: Family Retreat
10.0 out of 10, Exceptional, (2)
"The home had everything we needed. The amount of activities made it that we didn’t even have to leave the community if we didn’t want to. We spent three days relaxing at the pool and pond. The restaurant on site is exceptional. The location is perfect! We were able to take day trips to Cape Cod, Salem, Boston and Gloucester for whale watching. Pam, the host is very helpful and attentive. We were very happy with our experience and would recommend to friends and family! 10/10"
Clean Cottage w/Heated Pools - Hot Tub - Playground - Golf Cart: Family Retreat
Cottage at Summer Village Gated Waterfront Resort Community-20 Miles from Boston
10.0 out of 10, Exceptional, (1)
"This cottage, in Summer Village, was modern and comfortable, with a sunny front room, whose loungers we enjoyed! The resort community was fairly quiet, since it was after Labor Day. There were an active group of older adults who were quite friendly. The fact that the community was gated made it a little harder to have visitors. We really liked taking walks in the morning--some good hills! We were sorry the beach and pond were closed due to high algae levels--were told that it was not uncommon at...
Cottage at Summer Village Gated Waterfront Resort Community-20 Miles from Boston
Staycation + Work From Home in one private setting
10.0 out of 10, Exceptional, (16)
"we really enjoyed our week at Pawtuckaway. Great Location and host was very responsive."
Staycation + Work From Home in one private setting
Private Water Front Home on Sunset Lake, Private Beach, Boating & Swimming
9.6 out of 10, Exceptional, (43)
"This property was the perfect setting for our family gathering! There was plenty of parking and the house/property is private, yet close to grocery and other stores. Everyone that came, absolutely loved it - could not stop talking about how nice it was to have the yard set up the way it is along the lake with the fire pit and plenty of chairs we could all spread out and just enjoy our time together, perfect! One of my aunt's even claims she was at this exact same property 60 years ago!? We...
Private Water Front Home on Sunset Lake, Private Beach, Boating & Swimming
Enchanting Romantic Waterfront Cottage
10.0 out of 10, Exceptional, (10)
"Me and my family had a pleasant experience at Anna’s house we had everything we could have needed she went the extra mile to make sure she thought of everything. She answered me right away if I needed something. The house was so cute and well put together me and my husband stayed in the master bedroom and it had an adjustable bed which made it comfortable for how me and my husband sleep. It was so beautiful waking up in the morning to the view of the lake. We will definitely be staying with her...
Enchanting Romantic Waterfront Cottage
Historic Newburyport - new to VRBO - Rental at the historic Bartlet Mall
Historic Newburyport - new to VRBO - Rental at the historic Bartlet Mall
Remodeled Cottage retreat on the Lake, close to Boston but nestled in the woods
Remodeled Cottage retreat on the Lake, close to Boston but nestled in the woods
Beautiful waterview and water access from adorable cottage
Beautiful waterview and water access from adorable cottage
Inviting Summer Village Cottage: Golf Cart & More!
Inviting Summer Village Cottage: Golf Cart & More!
Lakefront Retreat w/ Kayaks, Grill, Fire Pit!
3.5 star property
Lakefront Retreat w/ Kayaks, Grill, Fire Pit!
Don't see what you're looking for?
See all available properties in Windham
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.

Other property types in Windham

The PondeRosa cottage at Cobbett's pond
10.0 out of 10, Exceptional, (10)
"The weekend that my girlfriend and I spent here was fantastic. Ana was very helpful and the cottage was beautiful and cozy. Hiking trails, food, bars, and stores all in 10 minutes or less driving range. Would easily stay here again, nothing negative to say at all!"
The PondeRosa cottage at Cobbett's pond
Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!
10.0 out of 10, Exceptional, (8)
"A short walk to the lake where we enjoyed kayaking and were the first to use the new firepit. Great location with all the amenities you would need."
Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!
Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.
10.0 out of 10, Exceptional, (2)
"Third time staying here we love everything the place has to offer. It’s great for my family. Also can’t beat the location."
Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private 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.

Recent reviews of Windham hotels
Expedia verified reviews