Freeport Holiday Rentals

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Holiday Rentals in Freeport

Exterior
Completely remodeled 2 bedroom apartment in Portland's West End
10.0 out of 10, Exceptional, (35)
"We very much enjoyed our stay at this location. The stairs were a bit scary, but with the light on, you'll be fine. :) Cozy spot for the three of us, well appointed and in a fantastic area. Very walkable, even down to the wharf. We are from a very non-walkable area, so it was amazing to see all the activity and places we could go just walking a bit. We enjoyed our first time in Maine, and can't wait to get back for a longer trip. Thanks to the hosts!"
The price is NZ$669
includes taxes & fees
21 May - 22 May
Completely remodeled 2 bedroom apartment in Portland's West End
Property grounds
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (15)
"This was a great spot for a weekend away! The unit is well equipped with higher end finishes and furnishings which makes the u it well worth visiting. The roof deck was a lovely addition as well! We left on Sunday so was happy to be able to move the car close to the unit Saturday evening to make packing a breeze."
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
View from property
Popham Beach Direct Oceanfront Cottage Steps to the sand
10.0 out of 10, Exceptional, (44)
"We had a great stay. Check in and communication was easy. Due to storm damage, our original booked cottage was not available and Deb offered us a different (much larger) home without added cost. We greatly appreciated it so we didn't have to cancel our vacation. The home was very clean and had everything we needed and then some. The area is beautiful and the beach was very clean. You cannot beat the views from the home. We look forward to staying here again!"
Popham Beach Direct Oceanfront Cottage Steps to the sand
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Exterior
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok
10.0 out of 10, Exceptional, (4)
"We had a very nice stay cabin met all our needs"
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok
Property grounds
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (124)
"We really enjoyed our stay. We loved being able to walk to the Eastern Promenade. The beds, including the sofa bed were very comfortable. Very cute and cozy There are stairs to enter the building for anyone with mobility issues. If you are unfamiliar with older buildings, the radiators do make some noise while heating in the winter."
The price is NZ$742
includes taxes & fees
27 May - 28 May
Glorious getaway on Portland's Eastern Promenade.
Fridge, microwave, oven, stovetop
Cozy, Elegant and Bright 2 bed in the East End
10.0 out of 10, Exceptional, (25)
"This was our first time in Portland, and the location was perfectly suited for us to see everything! We were able to walk to restaurants and a little market around the corner. The home was easy to access and we were always able to find a parking spot. The unit itself was really nice, although the living room did not have enough seating for our travel party (four adults; there was a couch that technically could fit three people but not comfortably). The unit was very clean and there were plenty...
The price is NZ$596
includes taxes & fees
27 May - 28 May
Cozy, Elegant and Bright 2 bed in the East End
Fridge, microwave, oven, stovetop
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
10.0 out of 10, Exceptional, (52)
"Artfully decorated and located walking distance to restaurants and parks. This was the perfect place for me and friends to visit around the table, watch a hockey game on TV, walk to restaurants, heat up take out, and was close to site seeing museums and light houses. The host was quickly available for suggestions. Check in and out was simple."
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
Property grounds
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (94)
"We celebrated our Mom’s 70th birthday in this beautiful space. It exceeded our expectations and the property manager David is the best!"
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Fridge, microwave, oven, stovetop
Convenient Portland home 3 miles from Downtown
10.0 out of 10, Exceptional, (8)
"The house was spotless and comfortable. We arrived in the middle of a snowstorm, and it was great to have the one-car attached garage, a heating system that worked well, someone who plowed the driveway and shoveled the snow shortly after we arrived, and a comfortable hot shower. Grocery stores and restaurants are nearby. Beds are comfortable, and there is a lot of closet space and drawer space. We would stay here again."
The price is NZ$1,166
includes taxes & fees
29 May - 30 May
Convenient Portland home 3 miles from Downtown
Outdoor pool
Beautiful oceanside Castle with private beach and seasonal swimming pool
10.0 out of 10, Exceptional, (29)
"This house was perfect for me, my married kids, their spouses, and my grandkids. The house was very clean and spacious. It rained the whole time, but we still had a great time. And Shannon, who manages the property, was very helpful and made sure we had everything we needed. Hope to return next year."
Beautiful oceanside Castle with private beach and seasonal swimming pool
Pool
Island cottage getaway
10.0 out of 10, Exceptional, (12)
"Coastal funky cottage, very comfortable and clean, terrific location and fabulous porch!"
Island cottage getaway
Fridge, microwave, oven, stovetop
Sensational House on Sebago Lake, Raymond, ME
10.0 out of 10, Exceptional, (33)
"Lovely property and location. Very clean with a fully stocked home. Will certainly be rebooking. Thank you!"
Sensational House on Sebago Lake, Raymond, ME
Terrace/patio
Waterfront, Luxury, Spacious home in Freeport!
9.8 out of 10, Exceptional, (16)
"In Freeport to spend time with the family. Lovely location, nice house, dog friendly, had a great weekend!"
Waterfront, Luxury, Spacious home in Freeport!
1 bedroom, WiFi
Quaint one-bedroom suite
9.8 out of 10, Exceptional, (37)
"Loved it!! Would definitely rent again"
The price is NZ$231
includes taxes & fees
19 May - 20 May
Quaint one-bedroom suite
Property grounds
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (99)
"Lovely home in a beautiful location. Very welcoming, cozy, and friendly. Easy check-in and check-out process. The owner was very accommodating and helpful. Made amazing memories and look forward to returning soon. Thank you so much!"
Charming 110-year former Inn 10' from the Ocean!
Aerial view
Ocean view Victorian
9.8 out of 10, Exceptional, (73)
"It was the best view of Casco Bay and such a unique home. Beautiful accommodations that are both historic yet updated for comfort and convenience. Our host was phenomenal! So friendly…we thought he was one of our neighbors from Louisiana (not just because of his homemade hot sauce that he sent home with us, but more importantly because of his hospitality!)"
Ocean view Victorian
Private kitchen
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, (88)
"We had a great time and this rental was very clean. The host was wonderful and easy to communicate with. My only tiny complaint is that the bedroom radiator was really loud (as they tend to be) and I am a light sleeper, so they kept me up. Not any fault of the rental, just is what it is. 15 minute walk to everything. Lovely, overall."
The price is NZ$877
includes taxes & fees
23 May - 24 May
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
View from property
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (75)
"This is a lovely little apartment, and we were very comfortable. I agree with the owner’s statement about the steps being steep; there is no landing at the top of these steps. We brought smaller bags, and that helped! I wouldn’t attempt this with a baby or a toddler. Everybody else: enjoy!"
The price is NZ$415
includes taxes & fees
20 May - 21 May
Adorable Portland getaway on the Eastern Promenade
Private kitchen
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (45)
"The kitchen was very well equipped. Living room was so cozy with the fire. Bed was super comfortable. The unit has really tall ceilings and is cozy. Only issue was the dog upstairs. They kept barking and whining."
Elegant condo - walk to Portland's best restaurants & Old Port
Private kitchen
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.4 out of 10, Exceptional, (21)
"Stayed for a weekend for bachelorette party! Very clean, close to downtown and loved the hot tub."
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
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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.

Other types of properties in Freeport you may be interested in

Deluxe Double Room, 2 Queen Beds (2 Queen)
Casco Bay Inn
2.0 star property
9.4 out of 10, Exceptional, (624)
"We were very impressed with our stay here. It’s close to LLBean and the surrounding shops. It was a great room. The staff was helpful, and breakfast was perfect. I loved the all day coffee in the lunch area."
The price is NZ$176
includes taxes & fees
19 May - 20 May
Casco Bay Inn
In-room safe, desk, blackout curtains, iron/ironing board
Holiday Inn Express Hotel & Suites Freeport, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, (1000)
"Thank you for providing a clean, spacious stay"
The price is NZ$254
includes taxes & fees
19 May - 20 May
Holiday Inn Express Hotel & Suites Freeport, an IHG Hotel
Business centre
The Freeport Hotel, Ascend Hotel Collection
2.0 star property
8.2 out of 10, Very good, (1000)
"Hotel being well maintained, breakfast good, good location."
The price is NZ$192
includes taxes & fees
20 May - 21 May
The Freeport Hotel, Ascend Hotel Collection
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Freeport holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Freeport. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Freeport. Seeing all the best attractions is bound to make you fall in love with Freeport. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Freeport short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Freeport?

Yes, there are holiday rentals in Freeport close to Wilbur's of Maine Chocolate Confections, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Freeport. Give yourself some extra time to check out the waterfront and cafes during your trip.

How many holiday rentals are there in Freeport?

Expedia has 28 holiday rentals for your stay in Freeport.

What can I see and do in Freeport?

Wolfe's Neck Woods State Park and Desert of Maine are a couple of scenic spots to enjoy the outdoors, whereas Freeport Historical Society is one of the cultural attractions. While here, LL Bean Flagship Store and Casco Bay are other places worth a visit.

What are holiday rentals like in Freeport?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Freeport. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.

Recent reviews of Freeport properties
Expedia verified reviews

Casco Bay Hotel, Ascend Hotel Collection

Casco Bay Hotel, Ascend Hotel Collection

5/5 Excellent
"The hotel was clean, check in was quick and the bed was comfortable. Breakfast was the expected waffles, pastries, cereal, sausage, eggs, coffee, juice. Some of the maintenance details were a little off like cream colored caulk on a white fixture, the level lines for the shower rod were scratched into the surround instead of pencil marked. It didn't change the stay but it made you wonder how that was accepted in what looked like a new or newly refurbished hotel."
A verified traveller stayed at Casco Bay Hotel, Ascend Hotel Collection
Posted 2 days ago
Casco Bay Hotel, Ascend Hotel Collection