Places to stay in Old Port, Portland

4.96 out of 5 average rating, 142 reviews

A white lighthouse stands at the edge of a rocky outcrop, surrounded by calm waters. The sky is filled with clouds illuminated by the setting sun, casting a warm glow over the scene. A stone walkway leads to the lighthouse, bordered by a railing.

Loft in Portland

Lily's Loft; Charming one bedroom studio

RebeccaRating, 5 stars5 months ago

We were in Portland overnight to visit with friends, and needed a place that was convenient to various places in town but also quiet and safe. Lilly's Loft was perfect for this. Julie and Joseph sent clear instructions on parking and checking in, and the loft was very clean and nicely furnished. We would definitely stay here again!

4.89 out of 5 average rating, 204 reviews

Condo in Kennebunk

Over 1000 Five Star Reviews! Walk to Dock Square !

AshleyRating, 5 stars2 weeks ago

I had a wonderful stay at this cozy Airbnb. The location was perfect, right in the heart of downtown, so it was super convenient to walk to shops, restaurants, and everything else we wanted to see. We also loved that it was dog friendly, which made our trip even better. The place was clean, comfortable, and exactly as described. The host was friendly and responsive, making check-in a breeze. Highly recommend!

Townhouse in Kennebunkport

A sandy beach scene is captured, featuring colorful kayaks arranged neatly in the foreground. Sunbathers and beachgoers enjoy the sunny weather, with umbrellas dotting the shoreline. A smooth ocean extends to the horizon, framed by a clear blue sky.

4.94 out of 5 average rating, 167 reviews

Great get away spot,historic home in Kennebunkport

TreenaRating, 5 stars4 months ago

I can’t say enough about this experience. The house was a great location for my mother’s 70th and Jennifer went the extra mile (literally) to make this a memorable experience for the celebration weekend. She is so easy to communicate with. Exceptional host, all the way around!

4.89 out of 5 average rating, 102 reviews

A serene bedroom is furnished with a comfortable queen bed dressed in neutral linens and accent pillows. Warm tones are complemented by decorative wall hangings, while a large mirror and plants enhance the light-filled space. A cozy chair and woven basket add to the inviting atmosphere.

Apartment in Portland

Portland Back Cove Hideaway-1 BR- With Patio

KristinRating, 5 stars3 months ago

I highly recommend staying here if you are visiting Portland! The apartment was adorable, very clean and in a perfect location. Alex had an entire list of recommendations that we found very helpful! We will definitely be back!

4.95 out of 5 average rating, 151 reviews

A colorful Welcome to Kennebunkport sign stands prominently at the bridge entrance. Below, a charming red building on stilts is seen, featuring a conical rooftop. Surrounding structures showcase classic New England architecture, enhancing the coastal charm of the area.

Home in Kennebunk

Quiet cozy cottage close to restaurants, beach

MikeRating, 5 stars6 months ago

Lori’s place was very cozy and a great screened in back porch. Perfect for morning coffee while taking in the scenery. Easily walkable to downtown and restaurants and right down the street from the beach. Nicely located for all things. We rented a car on our stay and travelled to Portland, Portsmouth NH and then close by towns to Kennebunk. All under an hours drive. We enjoyed our stay at Lori’s place.

4.83 out of 5 average rating, 139 reviews

A bright dining area features a large glass table surrounded by six black wooden chairs. Natural light filters through three large windows, and a simple floral centerpiece sits at the table's center. A modern chandelier hangs above, complementing the neutral-toned walls.

Apartment in East End

Fall in LOVE With PORTLAND, MAINE

OliviaRating, 5 stars1 month ago

Stayed for a weekend with 5 people - the space was perfect us! With 3 beds and 2 baths we didn’t feel on top of each other inside. We opted for free street parking which was never an issue. There’s a handful of coffee shops, restaurants and bars with 5-10 min walk. Old Port is about 20 min walk but very easy and safe. We loved being around the block from the ocean and east prom!!

Townhouse in Old Orchard Beach

The exterior of a three-story townhouse is visible, featuring white siding and a decorative star in red, white, and blue. A wooden deck with a white lattice railing is present at the entrance, complemented by flower pots along the base. Trees in full autumn foliage frame the scene.

4.82 out of 5 average rating, 34 reviews

Star House has Ocean view from the 3rd level deck.

AmandaRating, 5 stars8 months ago

Lovely Beach home! The place was not only comfortable, but also beautiful appointed, making our stay really enjoyable! Clean, lots of amenities, hosts easy to communicate and available! Lots of things to do around and beach is less than 5 minutes on foot. We definitely recommend your charming home! I hope to come back soon!

Vacation rentals for every style

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Popular amenities for Old Port, Portland places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Old Port, Portland's top sights

Old Port223 locals recommend

Portland Museum of Art412 locals recommend

Hannaford Supermarket280 locals recommend

Eventide Oyster Co.271 locals recommend

Rosemont Market & Bakery222 locals recommend

OTTO191 locals recommend

Other great vacation rentals in Old Port, Portland

Home in Old Orchard Beach

5 out of 5 average rating, 11 reviews

Stunning Beachfront Dream Home

StephanieRating, 5 stars6 days ago

We had an amazing stay at this beautiful house! Our family loved gathering around the large dining room table for dinners, making lasting memories together. The house was immaculate, and the beach access was unbeatable. Waking up to stunning waterviews each morning was truly special. Plus the location was perfect- just a short drive to Portland, Cape Elizabeth and Ogunquit. We would absolutely love to stay here again. Highly recommend!

4.93 out of 5 average rating, 58 reviews

A modern kitchen is highlighted with sleek white cabinets and a polished granite countertop. High-end stainless steel appliances, including a gas range, are featured. The open layout connects to a bright living area, where natural light fills the space through large windows.

Home in Scarborough

Gorgeous 4 BR home with HOT TUB

Elizabeth AnnRating, 5 stars1 week ago

The home was beautiful and matched the photos online. Clean and inviting! Gregory was responsive while booking and during our stay. Very kind and would stay here again for another girls weekend get away!

4.91 out of 5 average rating, 85 reviews

Cottage in Windham

Tranquil waterfront cottage

Jo-AnnRating, 5 stars6 months ago

This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.

4.97 out of 5 average rating, 63 reviews

Home in Gray

cozy 3 bedroom ranch with deck and screen porch

MichaelRating, 5 stars3 months ago

The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.

Home in Old Orchard Beach

A bright kitchen space showcases white cabinetry and stainless steel appliances. A large island with granite countertops features seating for three, complemented by pendant lighting. An adjacent dining area is visible with a table designed for six, creating an open, inviting environment.

4.98 out of 5 average rating, 89 reviews

Woods Lane Golf and Beach Vacation

MarjorieRating, 5 stars6 months ago

Our group of 5 adults were so pleased we chose to stay at Jason’s house in Old Orchard Beach. We first looked at places in Portland, but Jason’s spacious house offered a quieter setting, with parking and more amenities, at a better price. Comfortable beds, immaculate throughout. Very thoughtfully appointed, with nightstands on both sides of the beds, and superior blackout blinds in the bedrooms. And we ended up spending less time in Old Port, because we enjoyed exploring the towns south of Portland: Old Orchard Beach, Saco, Biddeford, and we found good restaurants (including Holy Donuts!) nearby. We had no issues: we contacted Jason to confirmed our arrival/departure and he responded within minutes. We highly recommend!

Townhouse in Old Orchard Beach

An inviting entryway is presented with a white wicker table and two blue-accented chairs. A large sign displays the name 'Beach House' against a turquoise background. Decorative items, including a glass jar and framed message, enhance the welcoming atmosphere, complemented by light-colored siding.

4.89 out of 5 average rating, 9 reviews

Unit 3 Getaway - Perfect for Families!

DanielleRating, 5 stars8 months ago

Perfect size for our family of 4. Location to the beach was a short walk across the street. Kitchen was modern and clean. The beds were comfortable. Pillows were available to use but we brought ours from home. Two bathrooms are always a plus with two teenage girls, only request from them was a full length mirror in the 2nd bedroom to check out their outfits. Owner reached out during our stay to check in and see if everything was going well. Very thoughtful. Would highly recommend a stay here.

Apartment in Old Orchard Beach

A spacious living area features a light-colored sectional sofa positioned around a wooden coffee table. Large windows provide natural light, and a dining area with wooden chairs can be seen in the background. Soft carpeting enhances the comfort of the space.

5 out of 5 average rating, 50 reviews

Horizon View Hideaway with Deck

ReneeRating, 5 stars6 months ago

The house is beautiful and very comfortable. We had everything we needed. The host was very friendly and responsive. We would definitely stay there again.