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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 30 Cottages in Windham with updated reviews, rates, and availability.

The Cozy Cottage
Outdoor dining

The Cozy Cottage

10.0 out of 10, Exceptional, (6)
"This was a clean cottage that we were instantly comfortable in. We appreciated the correspondence with the owner and will definitely refer friends. "
The Cozy Cottage
Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself
Property grounds

Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself

9.6 out of 10, Exceptional, (18)
"Our kids said the beds were the most comfortable beds they'd ever slept on, with the coziest blankets. The cabin was warm, cozy, and homey. Host was very nice and communication was timely and helpful. Beautiful view on the lake. Close to all amenities, shopping, and grocery stores."
Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself
Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.
Pool

Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.

9.2 out of 10, Wonderful, (5)
"The cabin is in a very nice, quiet and peaceful area. The property was clean and inviting. Once we figured how to work the pellet heater we were set. We were very pleased with our stay. "
Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.
Staycation + Work From Home in one private setting
Outdoor dining

Staycation + Work From Home in one private setting

10.0 out of 10, Exceptional, (18)
"Very nice hosts brought me chicken broth- came with a cold"
Staycation + Work From Home in one private setting
Charming 2-bedroom cottage in Westford, sandy beach, 2 pools, restaurant on site
Pool

Charming 2-bedroom cottage in Westford, sandy beach, 2 pools, restaurant on site

2.0 star property
10.0 out of 10, Exceptional, (1)
"My wife literally did not want to leave John's cottage at Summer Village. John updated and his wife tastefully decorated their cottage and thought of everything including spices, toiletries, swim toys and a fully stocked kitchen allowing for great home cooked meals. The location is very quiet and private abutting a nature preserve and the neighbors were friendly and welcoming. We swam in the pool and played on the beach every day. John promptly answered any questions we had and offered...
Charming 2-bedroom cottage in Westford, sandy beach, 2 pools, restaurant on site
Beach & pond Cottage
Exterior detail

Beach & pond Cottage

9.6 out of 10, Exceptional, (5)
"The cottage was well laid-out for a small to medium size family to stay. Golf cart was great for taking small children to nearby water features (swimming pools and lake). Other visitors and local residents were very friendly and courteous. Perfect place for a week away from hectic city life."
Beach & pond Cottage
Cozy 3 bedroom seasonal cottage with very short walk to private community beach
Exterior detail

Cozy 3 bedroom seasonal cottage with very short walk to private community beach

9.6 out of 10, Exceptional, (10)
"Good stay"
Cozy 3 bedroom seasonal cottage with very short walk to private community beach
The PondeRosa cottage at Cobbett's pond
Aerial view

The PondeRosa cottage at Cobbett's pond

10.0 out of 10, Exceptional, (19)
"Location worked perfect for us to be near family and friends "
The PondeRosa cottage at Cobbett's pond
Cottage at Summer Village Gated Waterfront Resort Community-20 Miles from Boston
Aerial view

Cottage at Summer Village Gated Waterfront Resort Community-20 Miles from Boston

10.0 out of 10, Exceptional, (2)
"Family reunion at our favorite summer place ."
Cottage at Summer Village Gated Waterfront Resort Community-20 Miles from Boston
Waterfront Cottage in Summer Village w/ Grill
Interior

Waterfront Cottage in Summer Village w/ Grill

2.5 star property
Waterfront Cottage in Summer Village w/ Grill
Peek-a-boo Lake Views & Yard: Windham Home
Interior

Peek-a-boo Lake Views & Yard: Windham Home

3.0 star property
Peek-a-boo Lake Views & Yard: Windham Home
Clean Cottage w/Heated Pools - Hot Tub - Playground - Golf Cart: Family Retreat
Outdoor pool, a heated pool

Clean Cottage w/Heated Pools - Hot Tub - Playground - Golf Cart: Family Retreat

10.0 out of 10, Exceptional, (3)
"We stayed here for 5 weeks. I had no idea when I booked it how amazing it would be. My kids say it was the best summer ever. The cottage is so cute. The location is amazing and all the amenities are amazing. They cottage community has so many activities going all the time, the beach and lake are so fun with a dock you can swim to, there is a restaurant on the weekends, riding the gold cart around, the swimming pool… I can’t say enough good about this place! I wish I owned one. Don’t hesitate to...
Clean Cottage w/Heated Pools - Hot Tub - Playground - Golf Cart: Family Retreat
Inviting Summer Village Cottage: Golf Cart & More!
Outdoor dining

Inviting Summer Village Cottage: Golf Cart & More!

Inviting Summer Village Cottage: Golf Cart & More!
Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!
Exterior

Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!

9.2 out of 10, Wonderful, (10)
"When we arrived we were immediately struck by how spotlessly clean the whole cabin was. And there were very thoughtful welcome packs too. The cabin has quaint cottage touches and the surround sounds from the woods were lovely. Very relaxing and comfortable environment. Full-sized washer and dryer came in handy. Don’t miss America’s Stonehenge just up the road. Would happily stay here again."
Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!
Enchanting Romantic Waterfront Cottage
Exterior

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
Riverfront New Hampshire Cottage w/ Boat Dock
Microwave, oven, stovetop, dishwasher

Riverfront New Hampshire Cottage w/ Boat Dock

3.0 star property
Riverfront New Hampshire Cottage w/ Boat Dock
Pond Access: Waterfront Littleton Hideaway!
Fridge, microwave, stovetop, coffee/tea maker

Pond Access: Waterfront Littleton Hideaway!

Pond Access: Waterfront Littleton Hideaway!
Remodeled Cottage retreat on the Lake, close to Boston but nestled in the woods
Terrace/patio

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
Lakefront Salem Retreat - Fish, Swim, Kayak & More
Living area

Lakefront Salem Retreat - Fish, Swim, Kayak & More

3.0 star property
Lakefront Salem Retreat - Fish, Swim, Kayak & More
Gated Resort Community
Interior

Gated Resort Community

Gated Resort Community
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 Windham

Peek-a-Boo Lake Views & Yard: Windham Home
Terrace/patio

Peek-a-Boo Lake Views & Yard: Windham Home

10.0 out of 10, Exceptional, (2)
"Lovely home in sweet neighborhood. The host was responsive to my communications. Very positive experience. "
Peek-a-Boo Lake Views & Yard: Windham Home
Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.
Pool

Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.

9.2 out of 10, Wonderful, (5)
"The cabin is in a very nice, quiet and peaceful area. The property was clean and inviting. Once we figured how to work the pellet heater we were set. We were very pleased with our stay. "
Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.
Home Away From Home in Lowell
Outdoor dining

Home Away From Home in Lowell

9.6 out of 10, Exceptional, (8)
"Very nice house with everything you would want!"
Home Away From Home in Lowell
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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