Cottage vacation rentals in Portland

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Top-rated cottage rentals in Portland

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Top guest favorite
A cozy outdoor seating area is set up on a gravel surface, featuring two wooden lounge chairs and a small table under a white umbrella. The blue exterior of the guest house is visible in the background, with steps leading to the entrance.
Cottage in Saco
4.94 out of 5 average rating, 459 reviews

Deja Blue~Guest Beach House

Our beach guest house is an oceanfront dream for a couple's retreat. Come relax by the sea. Listen to the waves crashing right outside your door. Disconnect or work while here we have fast WiFi for you. Enjoy this gem of a place on the coast of Maine as a year round escape. Come make some memories to cherish for a lifetime. All 4 seasons are beautiful here. Pro tip: Wake up early and observe the beautiful sunrise over the ocean. It is totally worth getting up early and will not disappoint.

Guest favorite
A serene waterfront scene captures the sun setting over a calm bay, with reflections in the water. In the foreground, tall grasses and wildflowers frame the image, leading to a dock with two Adirondack chairs arranged for relaxation.
Cottage in South Hiram
4.93 out of 5 average rating, 277 reviews

Cozy waterfront home on Merrymeeting Bay.

Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

Guest favorite
An entryway features a red door, two clocks on the walls, and a small bar table with two stools. A mirror is mounted above the table, and the space is complemented by wood accents and light-colored flooring leading to the kitchenette.
Cottage in Portland
4.9 out of 5 average rating, 593 reviews

Cozy & Quiet Modern Cottage

Modern studio cottage designed and maintained with sustainability and eco-friendliness in mind, located in a quiet and very safe Portland neighborhood only a 7-10 minute drive (and $10-13 Uber/Lyft ride) from downtown Portland, the Old Port, and most local attractions. The cottage is a walkable mile (+/-) from Allagash Brewing (and the 4 other breweries there), and is within walking distance (.5 mi) of the restaurants and bars at Morrill's Corner. This is an LBGTQIA- and BIPOC-friendly space.

Top guest favorite
Cottage in Buxton
4.97 out of 5 average rating, 160 reviews

Peaceful Cottage on Maine Flower Farm

Maine’s Peaceful Off-Season Escape Nestled just next door to Ferris Farm, our family-run flower farm, this charming cottage offers the perfect private space to rest and recharge. Even as the gardens rest for winter, there’s beauty all around. Stay in and enjoy slow, coffee-filled mornings, quiet walks around the property, and cozy, starlit evenings by the fire pit. Or take a drive and explore Portland’s diverse food scene. Perfect for a romantic retreat, solo escape, or remote work getaway.

Top guest favorite
A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.
Cottage in Brunswick
5 out of 5 average rating, 186 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Top guest favorite
The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.
Cottage in Pownal
4.99 out of 5 average rating, 428 reviews

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

Top guest favorite
The exterior of a three-story cottage is shown, featuring a light-colored wood siding and a set of stairs leading to double glass doors. A flag flutters in the breeze, and neatly trimmed shrubs and plants surround the entrance.
Cottage in East End
4.96 out of 5 average rating, 257 reviews

4br2ba House+parking@PeacefulOasis on Munjoy Hill

This standalone 1500sf 3-story cottage is set in an ideal location, close to the Eastern Prom, cafes, award-winning restaurants, breweries and the Old Port. -Main floor: well-equipped kitchen + open concept living/dining room -Upper floor: 3BR (1 queen, 1 full, 1 twin) + bath -Garden level: 1BR/1 bath (queen) with private entrance - Off-street parking for 1 car This charming home @ A Peaceful Oasis offers plenty of space, privacy & comfort, making it the perfect home base for your stay.

Top guest favorite
A cozy cottage is surrounded by lush trees and greenery. Two blue chairs are placed outside near the entrance, with a small table between them. A gas grill is positioned nearby, creating a welcoming space for outdoor relaxation and dining.
Cottage in Scarborough
4.97 out of 5 average rating, 252 reviews

Bright, clean, private cottage near Higgins Beach!

Nestled amongst the trees and located just 2 miles from beautiful Higgins Beach and just 5 miles to Portland, this recently renovated, sparkling clean, bright, private, stunning cottage is waiting just for you! Your private entrance is just steps away from your parked car. The cottage is 16 x 20 so it's super cozy! We live on the property (so we're here if you need us) but you are 100 feet from us, way out in the backyard. (It's private!) Our location is perfect for your Maine vacation!

Superhost
A cozy living area is displayed, featuring a combination of modern and vintage furnishings. A potted plant sits on a light blue coffee table, while a dining area with a round table is seen. The kitchen area and sliding barn door are visible in the background.
Cottage in Old Orchard Beach
4.92 out of 5 average rating, 334 reviews

#1 Cozy cottage minutes from the beach!

3 night Min. 6/1 to Labor Day. This charming one bedroom cottage is beautifully decorated with a blend of vintage pieces and modern decor, creating a cozy and stylish atmosphere. It features a fully stocked kitchen, complete with pots and pans, perfect for cooking when you choose to stay in. The cottage also includes a private patio with a gas grill and outdoor seating for your enjoyment. Just a short 7-minute walk to the beach and pier. And yes, pets are welcome at no extra charge.

Guest favorite
A tranquil view of the ocean is visible from a spacious wooden deck, featuring several white Adirondack chairs. The calm water reflects the clear blue sky and surrounding greenery, while distant islands can be seen along the horizon.
Cottage in Harpswell
4.9 out of 5 average rating, 166 reviews

Classic Maine Cottage - dock, sauna & kayaks

The Perfect Maine Cottage! On the edge of the ocean, carefully preserved with traditional details. Charming, open floor plan, with a wall of windows to the ocean. Sunny large wrap-around deck and screen porch creates beautiful outside spaces to enjoy. Perfect for listening to waves and watch lobstermen pull up their traps. Cathedral ceilings and Scandinavian design gives the cottage an exclusive feeling. Gentle stairs lead to the private deep water dock for all kinds of boating.

Top guest favorite
The exterior of the cottage features a large screened-in porch framed by tall trees. A pathway leads to the entrance, while colorful shrubs and a pumpkin add seasonal charm. The serene waters of the Sheepscot River are visible in the background.
Cottage in Edgecomb
4.98 out of 5 average rating, 322 reviews

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

Guest favorite
A cozy living area features a warm color palette with a sectional sofa adorned with textured blankets and cushions. A rustic coffee table sits in front of a mounted television. Natural light floods the space, highlighted by wall art depicting wildlife and an appealing area rug.
Cottage in Yarmouth
4.95 out of 5 average rating, 145 reviews

Modern cozy cottage in historic coastal Maine

Contemporary, newly-renovated cottage between Portland and Freeport. Spotless interior w/ full kitchen, Netflix/AppleTV+, premium Tuft+Needle bed, and washer/dryer. EV charging available. Walk down Main Street to shops, restaurants, and the scenic Royal River. Easy drives to downhill skiing and iconic beaches, Portland's renowned restaurants, LL Bean flagship, and top-rated Maine Brewing. Half way between Boston and Sugarloaf. Your ideal base for Maine adventures.

Popular amenities for Portland cottage rentals

Quick stats about cottage rentals in Portland

  • Total vacation rentals

    Explore 50 vacation rentals in Portland

  • Nightly prices starting at

    Portland vacation rentals start at G$18,803 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,310 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Portland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Portland rentals

  • 4.9 Average rating

    Portland stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    Portland's top spots, include Peaks Island, Crescent Beach State Park, and Portland Museum of Art

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