Vacation rentals in Cushing Island

A cobblestone street is framed by historic red brick buildings. Umbrella-covered tables sit outside local shops and cafes. Green and blue storefronts add color, while potted plants enhance the walkways. A friendly atmosphere invites leisurely strolls through the charming neighborhood.

4.98 out of 5 average rating, 149 reviews

Modern Luxury with Bay Views * 5 Star Location!

Well-appointed, high-end private apartment with wide plank pine floors sourced from Western Maine, luxury bathroom and bedroom. Shared patio with grill and fire pit. A short walk to the Eastern Prom or restaurants of the Old Port and Washington Street. I pay attention to details such as cleanliness, local coffee, quality linens, furniture and furnishings. Queen bed with a view of the harbor. This is a non-smoking, non-cooking space. Not suitable for infants children. Hi speed internet.

A cozy patio area features a comfortable seating arrangement, accompanied by a rustic coffee table. Lush greenery and potted plants provide a natural backdrop, while the warm glow of string lights creates a serene ambiance for relaxation.

4.94 out of 5 average rating, 141 reviews

Sopo Abode

Welcome to your garden oasis. Your home away from home. This elegantly styled garden level apartment in South Portland's crown jewel neighborhood, Sylvan Sites, is spacious, calm, and inviting. Have a sit in your private sauna, and take in the abundant birdsong of the neighborhood from your private back patio while you sip your morning coffee. Just down the road (5 minutes) to downtown Portland, Willard Beach, or Knightville, and 10-15 minutes to Scarborough and Cape Elizabeth beaches.

4.98 out of 5 average rating, 135 reviews

Yurt in Chebeague Island

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Water. Outdoor fire pit. WiFi . Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to the yurt.

A modern kitchen area is illuminated by natural light streaming through a skylight and a large window. A stainless steel sink is positioned under the window, complemented by wooden counters and open shelving. A single orange chair adds a pop of color, enhancing the minimalist design.

4.98 out of 5 average rating, 151 reviews

Peaks Island Master Bedroom Suite

Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

4.96 out of 5 average rating, 221 reviews

Willard Beach: Cozy Apartment with a King Size Bed

This luxurious first floor apartment is filled with sunshine all day long and on chilly nights the gas fireplace provides a warm ambiance. We think you’ll especially enjoy sinking into the velvet covered king size bed at night and stepping into the spacious shower that includes a rainfall shower head along with a handheld ... use either or both, as you please! The kitchen is equipped with quartz countertops, solid cherry cabinets and high end stainless steel appliances.

4.93 out of 5 average rating, 629 reviews

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

4.78 out of 5 average rating, 574 reviews

Downtown Studio, Walk Everywhere, Parking

The state of Maine requires all reservations must abide by current state travel restrictions. Please review before booking with us. You will love the location - just park at your reserved spot and forget about it! Great restaurants, bars, coffee shops, museums, Old Port, and Art Districts are all within 20 min walk. Fresh linens, towels, shampoo, french press, an insanely comfortable bed, and warm hospitality are provided, only bring your curious self!

Guest suite in South Portland

A charming storefront presents a colorful display with a large red sculpture and a vibrant flower garden. The shop window is adorned with playful designs and bright signage, while striped awnings provide shade over the entrance. Nearby buildings complement the quaint, inviting atmosphere.

5 out of 5 average rating, 251 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer, and cozy couch for lounging.

4.92 out of 5 average rating, 282 reviews

A bathroom doorway opens into a compact space featuring a white toilet and a small sink. Light blue walls create a soothing contrast with the warm wood flooring. A mirror and a few shelves are mounted above the sink, providing functional storage.

Guest suite in Portland

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

4.85 out of 5 average rating, 148 reviews

A charming beach cottage is nestled in a park-like setting along a quiet road. The ocean is visible in the background, framed by bare trees. The cloudy sky reflects soft shades of blue, while coastal rocks and waves can be seen nearby.

Cottage in Portland

Artist's Retreat

A 1900's beach cottage on Peaks Island, a 5 minute walk from the ferry, but nestled off the road in a park like, peaceful setting. Hear the waves at night from the backyard, walk 5 minutes to Sandy Beach for swimming and to Picnic Point, with its view of Cushing Island and Whitehead Pass. Experience the beauty of Peaks -- but take a 17 minute ferry ride into downtown Portland for award winning restaurants. The best of both worlds!

4.85 out of 5 average rating, 319 reviews

East End Oasis

2bed, 1bath-1st Floor Unit. Located in the middle of Portland's most desirable neighborhood - the top of Munjoy Hill in the East End of Portland. Hardwood floors throughout. The double lot offers a LARGE and PRIVATE fenced in yard, complete with 2 patios/sitting areas, a grill, and beautifully maintained flower/vegetable gardens. Wash & Dryer in Unit. One off street parking spot and city bus stop on the street.

Guest suite in South Portland

A light green door is positioned prominently against a softly painted wall. A small, wall-mounted shelf displays decorative items. Nearby, a wooden dining table with two chairs is illuminated by natural light filtering through a window with light, sheer curtains.

4.92 out of 5 average rating, 255 reviews

Top of the Hill So Po In Law

Lovely In law apartment in desirable Meeting House Hill area of South Portland .We were recently the hottest real estate market in the country .Conveniently located , 10 minutes to Portland , and on the doorstep of local beaches, State parks , restaurants ,unique boutique shops ,amazing bakeries and coffee , lunch and antiquing .All you need for a home away from home . Your going to love this neighborhood !

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Popular amenities for Cushing Island vacation rentals

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Free parking on premises

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Other great vacation rentals in Cushing Island

A private patio area features two comfortable chairs and a hanging chair, surrounded by wooden fencing. Soft lighting is present, creating a relaxed ambiance. Greenery and a potted flower add a touch of nature, complemented by stone pathway leading to the entrance.

5 out of 5 average rating, 3 reviews

Charming Victorian Getaway With Private Patio

TravisRating, 5 stars1 week ago

We had a wonderful visit at Colleen’s place!! The place is beautiful and very comfortable. The private deck area is a beautiful spot and so relaxing. Everything inside was given great attention and the art displayed is beautiful. You will not regret choosing this this as your vacation destination!!!

Private room in Peaks Island

A well-lit staircase is surrounded by light-colored walls and features a polished wooden banister. Framed artwork adorns the walls, while a console table and lamp are positioned near the bottom of the stairs. A patterned rug runs along the floor below.

4.84 out of 5 average rating, 226 reviews

Peaks Island stays with 2 night minimum

LindsayRating, 5 stars2 weeks ago

Lovely home on Peaks Island! Rhonda is such a warm, friendly host and went above and beyond to make sure we had everything we needed during our stay.

4.96 out of 5 average rating, 56 reviews

Home in Portland

Cheerful, Sunny, 3 Bedroom Island Home

Alex and CarissaRating, 5 stars2 weeks ago

We had a great stay at Capt Gene's! He was very helpful before our trip with giving ferry instructions which made our first day less stressful and more enjoyable! I would definitely recommend anyone to stay at Capt Gene's!

4.87 out of 5 average rating, 460 reviews

The hotel exterior showcases a modern facade characterized by gray and blue panels. Large windows reflect light and offer glimpses of indoor seating arrangements. Soft landscaping highlights the entrance, while warm light from fixtures adds to the welcoming appearance of the building.

Hotel room in Portland

Eateries, nightlife, galleries – walk to it all

DionisioRating, 5 stars5 days ago

Great place to stay near Portland’s Old Port and West End! Walkable to all the main things in the city.

Private room in South Portland

An historical cemetery marker stands prominently in the foreground, reading 'Old Settlers Cemetery - South Portland's Oldest Landmark 1658.' The backdrop features a serene view of the water with sailboats gliding by, framed by lush green grass and trees.

4.89 out of 5 average rating, 374 reviews

Airy Room in Antique Victorian - SOPO

HenriqueRating, 5 stars2 weeks ago

I thought it was great! It was exactly what the pictures and descriptions said it would be. The only thing I would watch out for is if you get the AIRY room it does face the street so you can hear cars passing by. I didn’t wake up at night because of it but I’m also not a light sleeper so it might be different for you. But like I said. This was probably the most accurate depiction of any place I’ve ever stayed at. So if it looks good to you on the app it’ll look good to you in person.

The image captures the serene view of a sandy beach with clear water, framed by greenery. Gentle waves lap at the shore, where a few people can be seen enjoying the water. In the background, a coastal landscape stretches along the horizon under a bright blue sky.

4.89 out of 5 average rating, 38 reviews

Willard By the Sea - 30 ft to the beach- 2nd floor

LisaRating, 5 stars2 weeks ago

We loved our long weekend at Kathy’s place on Willard Beach! It was easy to find and access, clean and comfortable, and full of character and charm. It was a quiet little place to land after exploring Portland that was very walkable and close to cute shops and restaurants. We traveled with our 3 year-old and 1.5 year-old, and it was easy to “toddler-proof.” Kathy was very responsive and helpful to recommend activities for us when our plans were foiled by rain. Would love to come back and stay again!

A serene coastal scene showcases two wooden structures perched on a rocky outcrop. The soft glow of the rising moon casts light over the water, while figures can be seen relaxing at a distance. Lush trees frame the background, adding natural beauty.

4.95 out of 5 average rating, 63 reviews

Peaceful Beach Getaway

LindseyRating, 5 stars6 days ago

Cynthia’s place is a quaint, private, beachside retreat that’s perfect to enjoy all that Portland has to offer. With a small beach just steps away, and Portland only a 10 min drive, this place is perfect if you’re looking for a relaxing Maine adventure. The bed was super comfy and the water pressure was awesome!

A bright workspace is created by a wooden desk positioned under three windows adorned with blinds. A blue chair sits at the desk, which is complemented by a small lamp and a potted plant. Natural light illuminates the room, enhancing the serene atmosphere.