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Our top choices for Freeport vacation homes

Spacious Country Home Freeport, Only 5 min to LL Bean!

Spacious Country Home Freeport, Only 5 min to LL Bean!
Freeport
9.6 out of 10, Exceptional, (15)
"It was a very relaxing house to stay in. Everything was provided in the kitchen, bathroom and bedrooms. Lots of room for all of us to mingle. "
United States
Carla S.
$548 nightly
The price is $575
Dec 24 - Dec 25
Total with taxes and fees
Spacious Country Home Freeport, Only 5 min to LL Bean!

Waterfront Spacious Luxury Home, 5 min to LL Bean!

Waterfront Spacious Luxury Home, 5 min to LL Bean!
Freeport
9.8 out of 10, Exceptional, (20)
"Very relaxing and quiet. Hosts were very accommodating "
United States
Heidi T.
$959 nightly
The price is $1,017
Jan 3 - Jan 4, 2026
Total with taxes and fees
Waterfront Spacious Luxury Home, 5 min to LL Bean!

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
$180 nightly
The price is $189
Jan 4 - Jan 5, 2026
Total with taxes and fees
Escape to Positive Outlook

Captain's Quarters 2BR Suite. Near everything. No fees. Pets welcome.

Captain's Quarters 2BR Suite. Near everything. No fees. Pets welcome.
Bath
8.6 out of 10, Excellent, (10)
"Nice, clean, cosy, conveniently located and easy enough to find. Great communication with host, comfortable beds and plenty of hot water. very responsive and would definitely consider using again. "
United States
A M.
$153 nightly
The price is $167
Jan 13 - Jan 14, 2026
Total with taxes and fees
Captain's Quarters 2BR Suite. Near everything. No fees. Pets welcome.

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (14)
"The views are amazing! A very relaxing place to be, and the house was clean and comfortable. "
United States
Monika G.
$294 nightly
The price is $311
Jan 11 - Jan 12, 2026
Total with taxes and fees
Fantastic Waterfront Views

5 Bedroom Lake House + Guest House with Hot Tub & Sauna!

5 Bedroom Lake House + Guest House with Hot Tub & Sauna!
Casco
10.0 out of 10, Exceptional, (14)
"We are a group of 4 that spend one week a year staying in a vacation home and playing golf. This was one of the best places we have stayed. Two buildings, lakefront, all amenities including hot tub and sauna. We highly recommend this vacation rental. Communication with property managers was first class."
United States
Bill G.
$643 nightly
The price is $650
Dec 24 - Dec 25
Total with taxes and fees
5 Bedroom Lake House + Guest House with Hot Tub & Sauna!

Generous Living in a Warm, Welcoming Home

Generous Living in a Warm, Welcoming Home
Topsham
$408 nightly
The price is $441
Jan 6 - Jan 7, 2026
Total with taxes and fees
Generous Living in a Warm, Welcoming Home

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (5)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
$339 nightly
The price is $370
Dec 27 - Dec 28
Total with taxes and fees
Beautiful 3BR Home with Office in Town of Brunswick with King beds

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

Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Brunswick
9.0 out of 10, Wonderful, (24)
"Nice place, I'd stay again!"
United States
Ronnie C.
$359 nightly
The price is $391
Jan 4 - Jan 5, 2026
Total with taxes and fees
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58)
"Perfect location on the water for a weekend getaway"
United States
Lydia G.
$309 nightly
The price is $337
Dec 31 - Jan 1, 2026
Total with taxes and fees
Camp Forever cottage

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

Chic 3-bedroom house in Munjoy Hill with off-street parking.
2.0 star property
Munjoy Hill
10.0 out of 10, Exceptional, (2)
"Absolutely fantastic stay! The house is clean, comfortable and has all the amenities to stay in. However with such a great location to all that Portland has to offer taking a quick walk to whatever strikes your fancy is highly recommended. The bakery on the corner has great coffee and baked goods. We didn’t need much from Doug but when I messaged him he was very responsive and accommodating. The beds are extremely comfortably. The location is quiet, within walking distance or a quick uber...
United States
Carl K.
$334 nightly
The price is $364
Dec 28 - Dec 29
Total with taxes and fees
Chic 3-bedroom house in Munjoy Hill with off-street parking.

Maine Luxury Home On the Sea

Maine Luxury Home On the Sea
Brunswick
$647 nightly
The price is $705
Jan 7 - Jan 8, 2026
Total with taxes and fees
Maine Luxury Home On the Sea

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
2.0 star property
Brunswick
$415 nightly
The price is $452
Jan 5 - Jan 6, 2026
Total with taxes and fees
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
9.8 out of 10, Exceptional, (8)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
United States
Karen T.
$485 nightly
The price is $490
Jan 2 - Jan 3, 2026
Total with taxes and fees
Orchid Harbor, Bailey Island 3BR

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2)
"Had a nice stay! House was great."
United States
Karen T.
$417 nightly
The price is $444
Dec 24 - Dec 25
Total with taxes and fees
Modern Getaway by the Sea

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (37)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
$330 nightly
The price is $360
Jan 4 - Jan 5, 2026
Total with taxes and fees
Modern & Sunny House Steps from the Promenade. Private Parking!

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very Good, (58)
"Quiet, close to everything and east to find."
United States
Jesse M.
$287 nightly
The price is $313
Dec 28 - Dec 29
Total with taxes and fees
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
$210 nightly
The price is $229
Dec 24 - Dec 25
Total with taxes and fees
Charming 1-bedroom ADU in wonderful Portland neighborhood

The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (6)
"This was the perfect spot for my friends and I who were attending a wedding down the road! Great location, lovely property and very clear instructions from the hosts! "
United States
Jen V.
$329 nightly
The price is $359
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Barnhouse with hot tub

Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home

Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home
3.0 star property
Gray
$859 nightly
The price is $956
Jan 4 - Jan 5, 2026
Total with taxes and fees
Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home
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.
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Top Freeport Hotel Reviews

Find out more about Freeport

Freeport Vacation Homes information

Number of reviews
265
Accommodation
515 Vacation Homes
Lowest Price
$167
Highest Price
$1,017

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