Apartment vacation rentals in Westbrook

Spacious 1BR w/ In-Unit Laundry

A warmly styled Portland apartment highly rated by 147+ guests — ideal for families or small groups. Tucked on a quiet residential street, you can walk to Rose Foods, Bird & Co., Back Bay, and great coffee, with a short Uber to the lively Old Port and Thompson's Point just around the corner. Inside: a light-filled private retreat with in-unit washer/dryer, a full kitchen, queen bed, twin bed, and sleeper couch with thoughtful touches throughout that make it feel like a true home away from home.

Value · Family · Bathroom

Quiet Comfy Victorian Escape

Spend your vacation, work-trip, or weekend getaway in this lovely renovated cozy 2 bedroom unit. Apartment 2 is located on the second floor of a three family house where you have access to all the modern appliances: refrigerator, W/D, microwave and TV in the living room. A brand new queen bed each bedroom, with seat in cozy seating in the living room. Located in the very central Oakdale neighborhood, this unit is steps from Deering Park, Sea Dogs stadium, USM Law School and Portland's Old Port.

Value · Family · Comfort

Apt in Victorian Mansion w/ Hot Tub, Parking, Pool

Contemporary styling with old-world charm, the Apartment in the Leonard Bond Chapman House offers a relaxing stay only 10 min to downtown. Whether you plan to soak in the shared hot tub, cool down in our seasonal pool, or relax by one of our fire pits, our half-acre yard offers a tranquil stay. The apartment boasts a newly renovated bathroom, radiant heated floors in both kitchen & bath, and a chef's kitchen. This grand apartment won't disappoint. L2 EV charging outlet on site #allarewelcome

Value · Family · Decor

Clean and Bright, Two Blocks to the Prom!

Clean and renovated 1890 2nd floor 3-bedroom apartment two blocks from the Eastern Prom. Enjoy walks to great restaurants, coffee shops, bars, breweries and the East End Beach. Short taxi ride to everything else downtown Portland has to offer! Street parking only, but typically easy and free! Apartment living, some noise. Building is Owner Occupied w/ long term tenants. Please be respectful, no loud parties! A/C installed first week of June to last week of Sept. Listing # STHR-00840-2018

Family · Value · Bathroom

Luxury Retreat In Back Cove | 10 Min to Downtown

Bike to downtown just 2 miles away. Ideal for a couple or family looking for a restorative getaway in a quiet, locals neighborhood. The architect owner designed and built this light-filled spacious eco-suite to meet the needs of the most discerning guest with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep soaking tub, fenced in backyard with deck, hammock, and pool - everything you need for a memorable Maine vacation!

Location · Family · Hiking

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.

Family · Location · Hospitality

Cozy 2 Bedroom Apartment Close to Portland

This is a newly renovated two bedroom, two story apartment in a great location (15 minutes to downtown Portland). The apartment is in walking distance to eateries, Riverbank Park, grocery stores and local breweries. It is also located across the street from the police station on a dead end street. The unit is child friendly and has a Pack 'n Play and high chair. (Please note that linens are not provided for the Pack n’ Play.)

Family · Location · Sleep quality

Back Cove Retreat | 3BR w/ Patio & 2-Car Parking

Historic charm meets modern comfort in Portland’s Back Cove. This renovated first-floor 3BR/2BA offers space, style, and parking for two cars — a rare Portland perk. Walk to the Back Cove trail, local coffee shops, restaurants, dog park, and sports fields. Or just a 5-minute drive to the Old Port and the bustling downtown waterfront area. The perfect home base for your Portland stay.

Location · Value · Sleep quality

Safe, Quiet, Friendly area

Situated in a wonderful, friendly, family neighborhood. Walking distance to restaurants, coffee shops, shopping, parks & trails. 10 minutes from The Old Port & Arts Districts and many other local attractions. Less than 2 miles from Thompsons Point concert and food truck venue! The unit is a Large (1200 square ft) and comfy 2 bedroom apartment located on the 2nd floor.

Location · Value · Beach

Lovely 4 Bedroom with free parking

Completely remodeled 1,600 sqft apartment on the first floor unit of a duplex. 2.5 miles from downtown Congress street. Great for groups and families. 2 parking spots and plenty of street parking available Front load washer and dryer 55” Samsung TV Large fenced in backyard with picnic table and plenty of space Airbnb license # STHR-005110-2023

Location · Value · Air conditioning

Cozy one bedroom on 2nd floor, close to Portland

Minimalist, boho vibe set in a vintage back drop. The trim, moldings and radiators are original to our 1890 home but with clean design you won't feel the clutter of vintage. Guests looking for a quiet retreat or calm vacation spot will enjoy. 15 minutes to Portland. 30 to LL Bean and Freeport for great shopping. Netflix etc in the room.

Value · Family · Checkout

Peaceful 1BR | Reading Nook | Near Portland

This bright second-floor apartment, located in a beautifully renovated 1890s home, offers a peaceful retreat in the heart of Westbrook. Just minutes from Portland’s dining, arts, and waterfront attractions, it’s the perfect balance of small-town charm and city convenience.

Location · Value · Cleanliness