Windham Vacation Rentals

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Vacation Rentals in Windham

The Perfect Beach Escape: Cozy 4-Bedroom Retreat

Old Orchard Beach ME

With a stay at this vacation home in Old Orchard Beach, you'll be on the beach, a 3-minute walk from Old Orchard Beach and a 2-minute drive from Old Orchard Beach Pier.

Kitchen

Washer

Charming 110-year former Inn 10' from the Ocean!

South Portland ME

With a stay at this vacation home in South Portland (Willard Beach), you'll be within a 15-minute drive of State Theatre and Thompson's Point.

Kitchen

Washer

Full sized home

Harpswell ME

$339 nightly

$369 total

Oct 27 - Oct 28

Total with taxes and fees

With a stay at this vacation home in Harpswell, you'll be by the sea, just steps from Casco Bay and a 3-minute drive from Ash Cove Pottery.

Kitchen

Washer

Waterfront Home on Beautiful Frye Island

Frye Island ME

When you stay at this vacation home in Raymond, you'll be steps from Sebago Lake.

Kitchen

Washer

Nature with in-town living that feels a world away. May-June-July special!!!

Portland ME

With a stay at this vacation home, you'll be centrally located in Portland, within a 5-minute drive of Maine Mall and Thompson's Point.

Kitchen

Washer

Three bedroom in United States of America, Freeport

Freeport ME

$879 nightly

$958 total

Oct 22 - Oct 23

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.

Kitchen

Washer

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.

Kitchen

Washer

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

Portland ME

With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of State Theatre and Thompson's Point.

Hot Tub

Kitchen

Charming 3-bedroom house steps to Pine Point Beach with backyard oasis

Scarborough ME

With a stay at this vacation home in Scarborough (Pine Point), you'll be within a 5-minute drive of Old Orchard Beach Pier and Old Orchard Beach.

Kitchen

Washer

Cozy Coastal House

Saco ME

With a stay at this vacation home, you'll be centrally located in Saco, a 5-minute drive from Old Orchard Beach Pier and 8 minutes from Old Orchard Beach.

Kitchen

Washer

NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available.

Peaks Island ME

With a stay at this vacation home in Peaks Island, you'll be on the waterfront, just steps from Casco Bay and a 3-minute drive from Battery Steele.

Kitchen

Washer

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Scarborough ME

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

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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.