Windham Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Windham

Three bedroom in United States of America, Freeport

Freeport ME

$924 nightly

$1,007 total

Jul 27 - Jul 28

Total with taxes and fees

With a stay at this vacation home in Freeport, you'll be on the waterfront, within a 15-minute drive of LL Bean Flagship Store and Casco Bay.

Steps from Old Port. New, Beautifully Appointed Home. Sleeps up to 11.

Portland ME

A stay at this vacation home places you in the heart of Portland, within a 15-minute walk of Casco Bay Lines Ferry Terminal and Cross Insurance Arena.

New Listing. 2BR+Bonus Sleeping Room in OOB. Walk to Beach & Amusement Park.

Old Orchard Beach ME

When you stay at this vacation home in Old Orchard Beach, you'll be near the beach, within a 15-minute walk of Old Orchard Beach and Palace Playland.

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island ME

With a stay at this vacation home in Bailey Island, you'll be on the beach, just a 1-minute walk from Casco Bay and 14 minutes by foot from Mackerel Cove.

Clean, Cozy, and Professional Waterfront Home- minutes to Portland

Falmouth ME

When you stay at this vacation home in Falmouth, you'll be on the waterfront, within a 10-minute drive of Casco Bay Lines Ferry Terminal and State Theatre.

Walk to beach, shuffleboard, and bunk room

Old Orchard Beach ME

With a stay at this vacation home in Old Orchard Beach, you'll be within a 5-minute drive of Old Orchard Beach Pier and Palace Playland.

Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)

Buxton ME

When you stay at this vacation home in Buxton, you'll be on the waterfront and 8 minutes by car from Saco River.

Beautiful ocean views and sunsets at this family-friendly, beachfront home

Harpswell ME

With a stay at this vacation home in Harpswell, you'll be on the beach, just steps from Casco Bay and a 4-minute drive from Mitchell Field.

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Brunswick ME

$514 nightly

$560 total

Aug 3 - Aug 4

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Brunswick, within a 15-minute drive of LL Bean Flagship Store and Casco Bay.

Manor Suite,cozy newly renovated,downtown & beach

Bridgton ME

$195 nightly

$213 total

Jul 27 - Jul 28

Total with taxes and fees

A stay at this vacation home places you in the heart of Bridgton, steps from Civil War Monument and 5 minutes by foot from Highland Lake.

Luxury Lakefront Estate on 138 Acres - Pickleball, Reunions & Weddings

Otisfield ME

Located in Oxford, this vacation home is on the waterfront, within a 15-minute drive of Saturday Pond and Island Pond.

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Falmouth ME

When you stay at this vacation home in Falmouth, you'll be on a lake and 14 minutes by car from Casco Bay.

Don't see what you're looking for?

See all available properties in Windham

View all properties

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.