Apartment holiday rentals in Westbrook

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.

Location · Value · Heating

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

Location · Value · Condition

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.

Family · Value · Layout

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 · Sleep quality

Cape Elizabeth Garden Apt+Beach+Close to Portland!

Bright, airy, two-story, 1000 sf apartment, with view of gardens. Off-street parking and private entrance. First floor living area with kitchenette, and sofa-bed, for additional guests. Second floor king bedroom with full bath. Ideally located a short walk to Kettle Cove Beach, and just minutes from Two Lights State Park, Crescent Beach, Higgins Beach and Robinson Woods Trail. Portland - voted the best restaurant city in the US - is a 10 minute drive. STR Permit #210701.

Family · Value · Amenities

Portland Back Cove Hideaway-1 BR- With Patio

Our quiet residential Back Cove neighborhood is your perfect retreat from a busy day exploring Portland. Take a short drive to the center of the city, or enjoy the waterfront walking and biking trail which loops around the cove. Dine at Tipo or Woodford F&B, two neighborhood favorites. Come home to this newly renovated space and relax on the patio! Our space can accommodate four guests. Great for a family, or close friends! We look forward to hosting you!

Family · Location · Nearby

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 · Long stay

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.

Location · Family · TV

Chic Portland Penthouse, 2BR

Enjoy a stylish experience at this centrally-located place. We are in the middle of all the excitement in the Old Port. Ride down the elevator and just out our front door you are steps to all the best that Portland has to offer. Shops, dining and night life all conveniently at your door step.

Family · Location · Kitchen

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

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. Large and comfy 2 bedroom apartment located on the 2nd floor.

Value · Family · Condition

Studio Apt In Walkable Distance to Restaurants

This is a private one bedroom efficiency apartment in a great location on Main Street in Westbrook. It is within walking distance of all Westbrook restaurants and breweries. The unit is very close to all the Portland attractions and is 15 minutes from downtown.

Value · Family · Outdoor spaces