Cottage holiday rentals in Portland

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Top-rated cottage rentals in Portland

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Guest favourite

Cottage in Pownal

4.99 out of 5 average rating, 350 reviews

Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike

Relax and unwind at this cozy post-and-beam cottage in a woodsy setting. Complete with all the modern amenities you will feel at home after exploring all that Maine has to offer. At day’s end ascend to the loft bedroom for a great night's sleep. Please note the current Maine travel restrictions: https://www.maine.gov/covid19 This custom post and beam cottage is brand new. Designed by John Libby, one of the most respected timber frame builders in New England, (www.housesandbarns.com) this space was thoughtfully designed and meticulously built specifically for your enjoyment. This cottage resides on the owner’s property, but is sited on its own two acres nestled among a beautiful stretch of Maine hardwood forest. Accessible via its own private driveway and surrounded by acres of pristine forest, it is the perfect place to relax among nature. No matter the season the exposed weathered Douglas Fir beams of the building will both welcome you and wrap you in a feeling of comfort and contentment. This complete home has all of the amenities. The kitchen includes natural unpolished granite countertops and brand new appliances including a stainless steel gas oven/range, dishwasher and refrigerator. The whitewashed walls of the hallway and bathroom provide a more modern feel, while showcasing all the wonderful knots of the Maine white pine from which it was milled. An easy-to-access, low/no step corner shower complete with floor to ceiling tile and an oversized vanity make time in the bathroom a pleasure. The open concept makes for a natural flow through the space and the sitting area comes complete with a queen sofa bed, TV and a gas fired wood-stove. The vaulted ceilings rise 22’ above the floor providing a spacious and beautiful feel. Radiant heat in the finished concrete floors make the space cozy and keep your feet warm. Oversized and lit stairs lead to the loft where you’ll find a king sized bed providing the opportunity for a great night’s sleep. Large windows make you feel as though your sleeping in the tree tops…come Fall this Oak and Maple forest comes alive with color. A ceiling fan keeps you cool, in the Summer and moves the heat around come Winter. Enjoy the beautiful outdoors on either the front or back deck, or from your own personal fire pit complete with granite bench. Don’t forget the s’mores! Guests have access to the post and beam cottage as well as the immediate surrounding area. We ask that the property boundaries are respected and that the guests do not go past the rock wall or onto the main house property or neighboring properties/horse farm. The post and beam cottage is on the same property as our primary residence but has it’s own driveway and is situated in a private clearing surrounded by beautiful forest. We will usually be available to welcome you personally and are happy to meet new people and make new friends but we also respect our guests privacy as we expect the same in return. Thank you! This post and beam cottage is in the small town of Pownal, 20 minutes from the wonderful restaurants, sights, and sounds of Portland. It's a 10-minute drive to Freeport and the L.L.Bean flagship store. Bradbury Mountain State Park is two miles away.

Guest favourite

Cottage in Saco

4.93 out of 5 average rating, 351 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 favourite

Cottage in East End

4.96 out of 5 average rating, 182 reviews

4br2ba House+parking@PeacefulOasis on Munjoy Hill

This is a standalone 1500sf 3-story cottage. Set in an ideal location, it's close to the Eastern Prom, cafes, award-winning restaurants, breweries & the Old Port. -Main floor: well-equipped kitchen+open concept living/dining room -Upper floor: 3BR (1 queen, 1 full, 1 single) + bath -Garden level: 1BR/1 bath Within a lush perennial garden of stone walls and pond, this private, peaceful setting is a perfect place to call home. Come explore; then settle in at our Peaceful Oasis. STHR-000924-2018

Guest favourite

Cottage in Topsham

4.95 out of 5 average rating, 238 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 favourite

Cottage in Sabattus

4.96 out of 5 average rating, 111 reviews

Maine lakehouse- close to Portland, 2.5 hr. Boston

Beautiful lake living: 2.5 hours from Boston, 45 min. from Portland. This cozy 2-bedroom home on Lake Sabattus with 110 feet of private lake frontage, sleeps four. All the amenities of home incl. a SS kitchen with newer appliances, air conditioning. Minutes to Lewiston/Auburn - close to dining and stores. Spend your days swimming, canoeing, kayaking and fishing, use our grills or lobster pot to prepare your dinner and relax by the fire pit, toasting s'mores while watching the gorgeous sunsets.

Superhost

Cottage in East End

4.93 out of 5 average rating, 307 reviews

Cozy Urban Cottage on Munjoy Hill

Snack and sip your way through the food mecca that is Portland, Maine from this conveniently located, newly renovated 1860s vintage/modern cottage. The artfully appointed two bedroom home is easy walking distance from the Eastern Prom, the Old Port, and Bayside, the craft-brewing district, allowing guests a one-of-a-kind getaway. Original wood floors are paired with modern furniture, soft linens, and techy touches (Bluetooth speakers, Apple TV). Come for the lobster, stay for the lifestyle.

Guest favourite

Cottage in Scarborough

4.97 out of 5 average rating, 192 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!

Guest favourite

Cottage in Brunswick

5 out of 5 average rating, 141 reviews

Lobstermen's ocean-front cottage

Be our guests and experience the life & beauty of Midcoast Maine. Relax and 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 property right on historic Route 24, a busy thoroughfare between Brunswick & the islands of Harpswell. All rooms have ocean views. There is a beach for your kayaks and the dock is ideal for seasonal fishing, exploring and swimming. Check out @gurnetvillage for photos and info.

Superhost

Cottage in Harpswell

4.88 out of 5 average rating, 140 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.

Guest favourite

Cottage in Bridgton

4.89 out of 5 average rating, 202 reviews

Rustic Pebble Cottage in beautiful Bridgton, Maine

Pebble Cottage is a one hundred year old quirky camp that was enlarged some years back. It is located in Bridgton near plenty of lakes and skiing. The public beach is a short skip down the hill. The cottage is a rustic little haven that was saved from demolition, and updated with a brand new bathroom, a cute little kitchen with a dishwasher, with two heat pumps to keep the space cozy and three homey comfortable bedrooms, a large yard with a picnic table, very quiet retreat.

Guest favourite

Cottage in Old Orchard Beach

4.97 out of 5 average rating, 193 reviews

#3 Couples Cottage Minutes from the Beach

3 night Min. stay 6/1 to Labor Day. Cottage #3 is a one-bedroom (king bed) recently renovated well-appointed with comfortable furnishings and updated finishes. It is outfitted with modern decor. The cottage has a fully stocked kitchen with pots and pans and utensils for those times when you may just want to stay in and cook. Full size washer dryer. A private fenced patio with a gas grill, table and chairs. Just a short 5-minute walk to the sandy beach. Yes we allow pets.

Guest favourite

Cottage in Standish

4.93 out of 5 average rating, 108 reviews

Peaceful Lakeside Maine Retreat

Beautiful and peaceful lakeside retreat in Maine. With plenty of space for you and your family or friends to spread out and relax, this fully updated home has all of the features you'll need to enjoy your vacation on the water. Or get away from it all while working remotely using our reliable WiFi. Only half an hour from Portland's lighthouses and exceptional seafood and craft beer. Just two hours from Boston, come and experience Maine - "the way life should be!"