Vacation rentals in Westbrook

The Chickadee Tiny House

The newly built Chickadee allows you to experience upscale tiny living within a stones throw of some popular local attractions. While we feel the Chickadee offers plenty of privacy from the inside you should make note that it is located in the middle of a neighborhood setting and the landscaping is still being worked on though won't be disruptive to your stay. Just under a mile from downtown Gorham 20 minutes to Portland Ski, swim, shop, eat, leaf peep, hike, the activities nearby are endless

Cozy Maine Cottage • Near Jetport & Coast

Cozy Cottage Retreat w/ Loft near Portland Welcome to your Maine escape. Reno barn offers a warm, cottage-inspired atmosphere with character, an open loft, and inviting spaces for rest and connection. Located mins from the airport and within walking distance to Allagash Brewing Company and other local favorites. A quick drive to downtown Portland, beaches, lighthouses, and live music. End your evenings on the private back deck — wine in hand, stars overhead, and nothing but quiet around you.

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Your crew will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

Private studio nestled in woods

New roomy studio located in a quiet residential neighborhood minutes from Portland. Guests access the apartment via their private deck and entrance. Full kitchen (stocked with cooking essentials and dishwasher), washer/dryer, and private parking for your convenience. Our goal is to be inclusive and welcoming to all. *Note: You must go up a full staircase to access apartment. The space is open to the stairs and therefore not safe for some children. Off-season discounted monthly rate available.

20 Min 2 Portland | Deck, Grill & Firepit | Dogs OK

Welcome to River's Edge Retreat! Our spacious, dog-friendly apartment is ideal for exploring Portland and beyond. With room for 8 and all the comforts of home, it's your cozy base for adventure. Sip coffee on the private deck, unwind by the firepit, or stroll to Westbrook’s shops and cafes. After a day of sightseeing, relax in comfort just 20 minutes from Portland’s vibrant Old Port. 15 Minute Walk to Downtown Westbrook 20 Minute Drive to Downtown Portland 12 Minute Drive to USM Gorham

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Modern stay Westbrook Maine

Welcome to our modern 1-bedroom basement retreat, nestled in the charming town of Westbrook, just a short 3-minute drive from the Portland, Maine. With its stylish design and upscale amenities, this Airbnb offers the perfect blend of comfort and convenience for your stay in the area. The bedroom features a Queen-size bed, a queen-size pull-out sofa in the living area, accommodating additional guests comfortably in the spacious living area. There’s a $200 pet fee per pet.

Riverfront guest house w/ patio

A beautiful one-bedroom guest suite with kitchenette and private entrance overlooking the river makes a perfect launching point for all that Portland and southern Maine have to offer. A comfortable oasis for one or two people. Bright, recently renovated with gleaming maple floors and large windows. Downtown Westbrook is a short walk away, with live music, great restaurants, an award-winning brewery, a bakery and coffee shop, great shops, and even a cat lounge.

Sebago Sunrise Yurt - Trail Access!

Nestled between Portland's fine dining and Sebago's outdoor fun, the Sunrise Yurt is a great camping spot to explore what Southern Maine has to offer. Park & take a short walk to the back 2 acres of my property. The yurt overlooks a meadow & faces the sunrise. Located with access to the Sebago to the Sea Trail - 28 miles of walking & biking paths. .5 mile walking distance to Presumpscot River. *Please read 'Show More' notes section for important details.

Cozy King bed apt near Portland with free parking

Enjoy a comfortable and relaxing getaway in this charming second-floor studio, owned and operated by a local family. Nestled in a quiet neighborhood, yet just minutes from Downtown Portland with easy access to I-95 and I-295, it offers the perfect mix of peace and convenience. This cozy studio features a brand-new King bed with a fresh mattress and pillows, along with a 3/4 bath—perfect for unwinding after a day of exploring the city or coast.

Garrison Cove Studio

Rare, Portland waterfront studio located in the heart of the historic Stroudwater neighborhood, awaits one or two guests looking for an urban hideaway. The studio occupies a 150 year old post and beam barn situated on the banks of the Stroudwater and Fore Rivers. Enjoy morning coffee on the river swing, meditate to the soothing sound of the nearby waterfall or linger over your favorite beverage in one of our comfy Adirondacks.

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C in the cabin. Please, no smokers, kids under 7, or guest pets. STHR-000718-2018