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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 25 Cottages in Windham with updated reviews, rates, and availability.

Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself
View from the lake

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
The Cozy Cottage
Outdoor dining

The Cozy Cottage

10.0 out of 10, Exceptional, (4)
"The cottage was exactly what my family needed for our visit . Tucked off the road and very quiet. Dan responded immediately to me whenever I reached out. "
The Cozy Cottage
Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!
The Firepit! Make a cocktail and warm up!

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!
The PondeRosa cottage at Cobbett's pond
Our cozy master bedroom with a queen size bed

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
Staycation + Work From Home in one private setting
Social distancing on a work from home island named "The Office." (joke)

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
Exterior

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

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.
Riverfront New Hampshire Cottage w/ Boat Dock
Property grounds

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
Heated pool next to gym, both overlooking the water.

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
Cozy 3 bedroom seasonal cottage with very short walk to private community beach
Front of House View

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
Beach & pond Cottage
Terrace/patio

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
Waterfront Cottage in Summer Village w/ Grill
Westford Vacation Rental | 2BR | 1BA | 5 Steps to Enter | 873 Sq Ft

Waterfront Cottage in Summer Village w/ Grill

2.5 star property
Waterfront Cottage in Summer Village w/ Grill
Inviting Summer Village Cottage: Golf Cart & More!
Westford Vacation Rental | 2BR | 1BA | 800 Sq Ft | Steps Required

Inviting Summer Village Cottage: Golf Cart & More!

Inviting Summer Village Cottage: Golf Cart & More!
Cottage at Summer Village Gated Waterfront Resort Community-20 Miles from Boston
Exterior

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
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
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
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
Remodeled Cottage retreat on the Lake, close to Boston but nestled in the woods
Miscellaneous

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
Southern New Hampshire lakefront
Property grounds

Southern New Hampshire lakefront

Southern New Hampshire lakefront
Gated Resort Community
Room

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.
Don't see what you're looking for?
See all available properties in Windham
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Windham

Peek-a-Boo Lake Views & Yard: Windham Home
Windham Vacation Rental | 5BR | 3BA | Steps Required | 2,766 Sq Ft

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

10.0 out of 10, Exceptional, (1)
"We have rented thru VRBO before. This was by far our best experience. The house had everything we needed (no running out first thing for toilet paper) Best of all was the Christmas tree and decorations. It really made it “home for the holiday.”The agent and owners were super communicative, let us know what and where’s promptly.I can’t thank them enough for the experience. Our dog loved the space it trapped in a hotel room."
Peek-a-Boo Lake Views & Yard: Windham Home
Charming 3-bedroom house with fitness room and WiFi in lovely Georgetown
Property grounds

Charming 3-bedroom house with fitness room and WiFi in lovely Georgetown

Charming 3-bedroom house with fitness room and WiFi in lovely Georgetown
Potager Farm Historic Private Townhouse Sleeps 4 with Pool.
Exterior

Potager Farm Historic Private Townhouse Sleeps 4 with Pool.

2.0 star property
Potager Farm Historic Private Townhouse Sleeps 4 with Pool.
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

Why book your cottage in Windham with Expedia?
We think that traveling should be easy, so if you’re chasing cottages in Windham at a nice price, Expedia has got your back. Save money and choose an inexpensive option surrounded by nature, or splurge on an upscale cottage to pamper your loved ones.
How can I find cheap cottages in Windham?
The easiest way to get cheap cottages in Windham is with Expedia’s handy filter tool. Refine your search results by budget, amenities and star rating to nab unbeatable rates in just a few clicks.