Search Windham Cottages
Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Windham cottages
1 Mi to Maine Street! Mcm-style Home in Brunswick
1 Mi to Maine Street! Mcm-style Home in BrunswickBrunswick
$275 nightly
The price is $300
Jul 16 - Jul 17
Total with taxes and fees
'Osprey Cottage' South Freeport Home on Casco Bay!
'Osprey Cottage' South Freeport Home on Casco Bay!Freeport
8.8 out of 10, Excellent, (22 reviews)
"This was an adorable cottage in a picturesque location. The cottage was clean and comfortable, right on the water. Additional friends stayed in the adjacent Heron cottage, and we joined them on the patio for a fire one evening as summer faded to autumn."
John J.
$593 nightly
The price is $644
Jul 19 - Jul 20
Total with taxes and fees
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Dog Friendly, Relaxing Cottage Stay • Steps Away from The BeachOld Orchard Beach
9.8 out of 10, Exceptional, (76 reviews)
"Place was great and fenced in backyard for our dog. "
Billy N.
$318 nightly
The price is $346
Jul 5 - Jul 6
Total with taxes and fees
Cottages by the Sea #1 by Bayley Vacation Rentals
Cottages by the Sea #1 by Bayley Vacation RentalsSurfside
10.0 out of 10, Exceptional, (7 reviews)
"Clean place, had everything we needed, and can’t beat the location. Will definitely be back."
Matthew J.
$1,089 nightly
The price is $1,179
Jul 13 - Jul 14
Total with taxes and fees
Renovated 2Bd Cottage 10min walk to Beach.
Renovated 2Bd Cottage 10min walk to Beach.Old Orchard Beach
7.2 out of 10, Good, (12 reviews)
"Was as advertised."
Andrew H.
$383 nightly
The price is $387
Jul 5 - Jul 6
Total with taxes and fees
Cozy one bedroom cottage, 50 feet from the beach in OOB.
Cozy one bedroom cottage, 50 feet from the beach in OOB.Old Orchard Beach
9.6 out of 10, Exceptional, (4 reviews)
"Great location to the beach and the pier! "
Pamela C.
$481 nightly
The price is $524
Jul 5 - Jul 6
Total with taxes and fees
Little Miss Cottages - One Bedroom Cottage
Little Miss Cottages - One Bedroom CottageOld Orchard Beach
9.0 out of 10, Wonderful, (7 reviews)
"Clean, very good communication with the host."
Brandon F.
$402 nightly
The price is $438
Jul 5 - Jul 6
Total with taxes and fees
Cottages By The Sea #2 by Bayley Vacation Rentals
Cottages By The Sea #2 by Bayley Vacation RentalsSurfside
10.0 out of 10, Exceptional, (2 reviews)
"Perfect little getaway."
Tish L.
$927 nightly
The price is $1,002
Jul 24 - Jul 25
Total with taxes and fees
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.
Find vacation rentals that suit your style
Cabins
Private vacation homes
Save an average of 15% on thousands of hotels when you're signed in
Top Windham Hotel Reviews
Comfort Inn South Portland Airport
10/10 Excellent
Find out more about Windham
Windham Cottages information
Number of reviews | 200 |
|---|---|
Accommodation | 427 Cottages |
Lowest Price | $300 |
Highest Price | $1,179 |
Frequently asked questions
Explore a world of travel with Expedia
- Cabin Rentals in Westbrook
- Cabin Rentals in Old Orchard Beach
- Falmouth Hotels
- Motels in Westbrook
- Hostels in Windham
- Guest Houses in Westbrook
- Cabin Rentals in Portland
- Scarborough Hotels
- Guest Houses in Windham
- Apartments in Portland
- Oceanfront Hotels in Portland
- Downtown Portland Hotels
- Motels in Windham
- Kennebunkport Hotels
- Cottages in Old Orchard Beach
- Hotels near Portland Intl. Jetport
- Ogunquit Hotels
- Cabin Rentals in North Windham
- Motels in Portland
- Pet-Friendly Hotels in Portland
- Old Orchard Beach Hotels
- Motels in Gorham
- Oceanfront Hotels in Old Orchard Beach
- Cottages in Gorham
- Cabin Rentals in Windham
- B&B in Westbrook
- Freeport Hotels
- B&B in Windham
- Cabin Rentals in Falmouth
- Hotels with Free Airport Shuttle in Portland
- Vacation Homes in Westbrook
- Rv Parks in Westbrook
- B&B in North Windham
- Rv Parks in Gorham
- B&B in Portland
- Resorts in Windham
- B&B in South Coast
- Cheap Hotels in Portland
- South Portland Hotels
- Vacation Homes in Little Falls-South Windham
- Rv Parks in Windham
- Wells Hotels
- B&B in Gorham
- Condo Rentals in Little Falls-South Windham
- Old Port Hotels
- Inns in North Windham
- Windham Hotels
- Portland Hotels
- Flights from Newark Liberty Intl. Airport (EWR) to Portland (PWM)
- Flights from Philadelphia (PHL) to Portland (PWM)
- Flights from Richmond (RIC) to Portland (PWM)
- Flights from New York (JFK) to Portland (PWM)
- Flights from Detroit (DTW) to Portland (PWM)
- Flights from Boston (BOS) to Portland (PWM)
- Flights from Seattle (SEA) to Portland (PWM)
- Flights from Cincinnati (CVG) to Portland (PWM)
- Flights from Nashville (BNA) to Portland (PWM)
- Flights from New York (LGA) to Portland (PWM)
- Flights from Orlando (MCO) to Portland (PWM)
- Flights from Fort Lauderdale (FLL) to Portland (PWM)
- Flights from Washington (IAD) to Portland (PWM)
- Flights from Chicago (ORD) to Portland (PWM)
- Flights from Cleveland (CLE) to Portland (PWM)
- Flights from Raleigh (RDU) to Portland (PWM)
- Flights from Houston (IAH) to Portland (PWM)
- Flights from St. Louis (STL) to Portland (PWM)
- Flights from New York (NYC) to Portland (PWM)
- Flights from Minneapolis (MSP) to Portland (PWM)
- Flights from Indianapolis (IND) to Portland (PWM)
- Flights from Miami (MIA) to Portland (PWM)
- Flights from Baltimore (BWI) to Portland (PWM)
- Flights from San Francisco (SFO) to Portland (PWM)
- Flights from Atlanta (ATL) to Portland (PWM)
- Flights from Pittsburgh (PIT) to Portland (PWM)
- Flights from Charlotte (CLT) to Portland (PWM)
- Flights from Jacksonville (JAX) to Portland (PWM)
- Flights from Washington (DCA) to Portland (PWM)
- Flights from Austin (AUS) to Portland (PWM)
- Flights from Columbus (CMH) to Portland (PWM)
- Flights from Hartford (BDL) to Portland (PWM)
- Flights from Tampa (TPA) to Portland (PWM)
- Flights from Dallas (DFW) to Portland (PWM)
- Flights from Los Angeles (LAX) to Portland (PWM)
- Flights from Portland (PDX) to Portland (PWM)
- Flights from Denver (DEN) to Portland (PWM)
- Flights from Salt Lake City (SLC) to Portland (PWM)
- Flights to Portland
- Flights from Portland Intl. Jetport
- Flights from Phoenix (PHX) to Portland (PWM)
- Flights from Tucson (TUS) to Portland (PWM)