Windham Vacation Rentals

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Vacation Rentals in Windham

The Moonglow! A beautiful ocean view house in Biddeford!

Biddeford ME

With a stay at this vacation home in Biddeford, you'll be near the beach, within a 15-minute drive of Engine and Fortunes Rock Beach.

Kitchen

Washer

Sunny Modern Oasis in Portland’s Trendy East End

Portland ME

A stay at this vacation home places you in the heart of Portland, steps from Casco Bay and 4 minutes by foot from Portland Observatory.

Kitchen

Washer

Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

Old Orchard Beach ME

$1,256 nightly

$1,369 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

With a stay at this vacation home in Old Orchard Beach, you'll be by the sea, within a 10-minute drive of Engine and Old Orchard Beach.

Hot Tub

Kitchen

Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

Poland ME

Located in Poland, this vacation home is on the waterfront, within a 15-minute drive of Tripp Pond and The Willows Flea Market.

Hot Tub

Kitchen

Large, light filled 4 bedroom house - walk to ocean and ferry

Peaks Island ME

With a stay at this vacation home in Peaks Island, you'll be by the ocean, just a 1-minute walk from Casco Bay and 6 minutes by foot from Richard Boyd Art Gallery.

Kitchen

Washer

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, within a 10-minute drive of Engine and Old Orchard Beach.

Kitchen

Washer

Bright & breezy beach house w/ private backyard, central AC, & relaxing hot tub

Old Orchard Beach ME

With a stay at this vacation home, you'll be centrally located in Old Orchard Beach, within a 10-minute drive of Engine and Harmon Historical Museum.

Hot Tub

Kitchen

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

Old Orchard Beach ME

$473 nightly

$515 total

Dec 9 - Dec 10

Total with taxes and fees

With a stay at this vacation home in Old Orchard Beach, you'll be within a 10-minute drive of Engine and Harmon Historical Museum.

Kitchen

Washer

Beautiful house on the Harpswell Peninsula over looking Casco Bay

Harpswell ME

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

Kitchen

Washer

Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

Scarborough ME

Located in Scarborough, this vacation home is on the waterfront, a 4-minute drive from Nonesuch River Golf Club and 7 minutes from Maine Mall.

Hot Tub

Kitchen

Entire Home In Saco Maine + GYM 3.5mil to Old Orchard Beach. Coastal Retreat!

Saco ME

With a stay at this vacation home in Saco, you'll be within a 5-minute drive of Engine and Saco Museum.

Kitchen

Washer

Spectacular Oceanfront Estate with Beautiful Sunsets on 8 acres

Harpswell ME

With a stay at this vacation home in Harpswell, you'll be on the waterfront, just steps from Casco Bay and a 5-minute drive from Lower Goose Island.

Kitchen

Washer

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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.