Photo by Carolyn Baker Reck

Harpswell Holiday Rentals

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Holiday Rentals in Harpswell

Full sized home
9.6 out of 10, Exceptional, 4 reviews
"Great place to stay. Host was helpful and responsive."
The price is NZ$561
includes taxes & fees
2 Jun - 3 Jun
Full sized home
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
9.8 out of 10, Exceptional, 26 reviews
"Just got back to NYC after spending 3 nights at the house with my dog. I already miss it. It's practically on top of the water, and sits in a very private, quiet and secluded location on a heavily wooded lot. It's a bit off the beaten path, but still a relatively short drive (10-30 mins, depending) to anywhere within the Harpswell/Brunswick area. Comfortable bed and furniture. The outdoor furniture seemed brand new (Adirondack chairs). It's a very cozy house that's perfect - even spacious - for...
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Portside - Make everlasting memories from this beautiful waterfront home
9.4 out of 10, Exceptional, 15 reviews
"The spaciousness and location made this house ideal for us. Watching the tide roll in, listening to spring and ocean birds, playing games and doing puzzles kept us busy and enjoying each moments."
Portside - Make everlasting memories from this beautiful waterfront home
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Bay-View. Waterfront Log cabin on the bay. Pet Friendly.
9.8 out of 10, Exceptional, 22 reviews
"Place was clean when we arrived. Cabin and lot location was very quite and locate where you couldn't see neighbors from the back deck. Very relaxing weekend. I would stay here again. View of the water was amazing."
Bay-View. Waterfront Log cabin on the bay. Pet Friendly.
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
8.8 out of 10, Excellent, 33 reviews
"Great views. House pretty clean & supplies were fine except only 3 coffee cups for 6 adults. VACasa said they would get more cups. They failed, never received. Some lights didn't work & lots of dead bugs in light fixtures."
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
Rent a room in the gorgeous Holt House
8.4 out of 10, Very good, 19 reviews
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
Unique oceanfront home with a deck, tons of natural light, & amazing views
8.8 out of 10, Excellent, 43 reviews
"We needed a quiet place to visit with elderly aunt and uncle. This was a great place with all the living space on the same floor with spacious area to visit."
Unique oceanfront home with a deck, tons of natural light, & amazing views
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, 17 reviews
"Excellent apartment in Old Port area of Portland. Bright, clean, updated, comfortable bed and furniture, lots of amenities. Would definitely stay there again!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Popham Beach Direct Oceanfront Cottage Steps to the sand
10.0 out of 10, Exceptional, 44 reviews
"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
Completely remodeled 2 bedroom apartment in Portland's West End
10.0 out of 10, Exceptional, 35 reviews
"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$749
includes taxes & fees
13 Jun - 14 Jun
Completely remodeled 2 bedroom apartment in Portland's West End
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, 45 reviews
"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."
The price is NZ$768
includes taxes & fees
3 Jun - 4 Jun
Elegant condo - walk to Portland's best restaurants & Old Port
East Boothbay Waterfront One room Condo.Waterview from in side this room
10.0 out of 10, Exceptional, 106 reviews
"EXCELLENT AND ENJOYABLE"
East Boothbay Waterfront One room Condo.Waterview from in side this room
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, 88 reviews
"We were in Portland for my daughter’s graduation. Had a very nice weekend trying different restaurants and enjoying lobster rolls."
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Vintage, Log Cabin in the Woods with Beach Club Access About One Mile Away
8.0 out of 10, Very good, 32 reviews
"We really enjoyed our stay at this cabin. Authentic vintage experience! Off course, if your are looking for a neet and sophisticate lodding, it might not be the place for you… but it was perfect for us! Very well located, near a private beach with 2 kayaks and chairs for our convinience. Also very near to the action of Boothbay Harbor that was a nice discorery! The cabin is very confortable, with everything we needed to prepare a nice meal and relax at anytime of the day. The only thing that...
Vintage, Log Cabin in the Woods with Beach Club Access About One Mile Away
Private Oceanfront Home on 10 Acres -- 2 Fireplaces, 4 Decks & Grill
8.8 out of 10, Excellent, 12 reviews
"My family and I loved this place so much that we definitely want to come back and stay again. Beach combing was fun looking for interesting rocks and seaglass. It was also nice sitting out the huge rocks and admiring the water. Driving around the town of Boothbay was amazing. The people were so friendly and the town has alot of charm. The house was another part of the trip that made it memorable. It had plenty of windows to be able to get a view of the water. The house was well equipped and the...
Private Oceanfront Home on 10 Acres -- 2 Fireplaces, 4 Decks & Grill
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
9.4 out of 10, Exceptional, 71 reviews
"We enjoyed the tranquility of the cottage and we appreciated the antiques connecting the cottage to the past/ history of the area. No issues with our stay. Location was good; the drive to daily activities not tremendous. Loved the village, and the people were so friendly. Great escape from every day life."
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
7.2 out of 10, Good, 7 reviews
"This home was clean, bright and comfortable. Great location, no issues. Would definitely stay here again."
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, 99 reviews
"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!
Riverfront condo w/ deck overlooking the water - steps to dining & shopping
9.2 out of 10, Wonderful, 25 reviews
"The space was very clean and comfortable, great location and amenities. Will definitely be returning!"
Riverfront condo w/ deck overlooking the water - steps to dining & shopping
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
8.8 out of 10, Excellent, 20 reviews
"Clean and easy to access, nice property for a short stay. Easy communication."
The price is NZ$683
includes taxes & fees
1 Jun - 2 Jun
Spacious and Contemporary Condo in the Heart of Portland - Close to 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.

Other types of properties in Harpswell you may be interested in

Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, 1,193 reviews
"Hotel feels like a home. It’s clean and beautiful "
The price is NZ$548
includes taxes & fees
2 Jun - 3 Jun
Portland Harbor Hotel
Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.6 out of 10, Excellent, 1,528 reviews
"Easy check in an out, friendly staff, free parking which is a plus, close to airport and central to a lot of restaurants and shopping. Bed was nice and comfortable. "
The price is NZ$135
includes taxes & fees
2 Jun - 3 Jun
Casco Bay Hotel, Ascend Hotel Collection
Canopy by Hilton Portland Waterfront
4.0 star property
9.4 out of 10, Exceptional, 654 reviews
"Great hotel in a good location along the waterfront. The rooms were lovely, and the rooftop bar is great. "
The price is NZ$508
includes taxes & fees
2 Jun - 3 Jun
Canopy by Hilton Portland Waterfront
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 Harpswell 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 Harpswell. 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 Harpswell. Seeing all the best attractions is bound to make you fall in love with Harpswell. 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 Harpswell short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Harpswell?

Yes, there are holiday rentals in Harpswell close to Ash Cove Pottery, or you can select a more secluded option if you're looking for a relaxing stay. Harpswell is known for its seafood restaurants and ski areas. Make sure you have time to check out the mountain views while you're in the area.

What are some of the best holiday rentals that Harpswell has to offer?

Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces: This holiday home rental outside of Harpswell is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals are there in Harpswell?

Expedia has 85 holiday rentals for your stay in Harpswell.

What’s there to see and do in Harpswell?

Family-friendly attractions include Ash Cove Pottery, whereas Lower Goose Island is a spot to enjoy the outdoors. In the wider area, you’ll find Bailey Island Bridge and Maine Street.

What’s a holiday rental in Harpswell like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Harpswell. Holiday rentals provide amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family trip or a small group gathering.

Recent reviews of Harpswell properties
Expedia verified reviews