Freeport Vacation Rentals

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Vacation Rentals in Freeport

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

Fantastic Waterfront Views

Phippsburg ME

$350 nightly

$373 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

With a stay at this vacation home in Phippsburg (West Point), you'll be within a 15-minute drive of Casco Bay and Popham Beach State Park.

Kitchen

Washer

Captain's Guest Room w/private bath. Walk to everything.

Bath ME

With a stay at this vacation home in Bath, you'll be within a 10-minute walk of Chocolate Church and Markings Gallery.

Pet friendly

Free WiFi

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 7 minutes by foot from Umbrella Cover Museum.

Kitchen

Washer

Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock

Woolwich ME

Located in Woolwich, this vacation home is within a 5-minute drive of Kennebec River and Markings Gallery.

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

Lone Pine Cottage Maine - Chef’s Kitchen

Bath ME

When you stay at this vacation home in Bath, you'll be by the sea, within a 15-minute walk of Maine Maritime Museum and Kennebec River.

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

Chic 3-bedroom house in Munjoy Hill with off-street parking.

Portland ME

$495 nightly

$540 total

Dec 28 - Dec 29

Total with taxes and fees

With a stay at this vacation home in Portland (Munjoy Hill), you'll be steps from Casco Bay and Portland Observatory.

Kitchen

Washer

New 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.

Kitchen

Washer

Beautiful Oceanfront House- Stunning Water Views

Harpswell ME

Located in Harpswell, this vacation home is a 1-minute drive from Casco Bay and 7 minutes from Androscoggin River.

Washer

Dryer

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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.