Family-friendly holiday rentals in Westbrook

Light-Filled Getaway with Private Porch

Spacious (1100 sqft), updated early Victorian (1838) apartment bordering the Arts District in Portland's historic and beautiful downtown West End. The apt. has great natural light, ample workspace, free on-street parking, a private garden entrance, and a sheltered, leafy screened porch. With a Walk Score of "95-A Walkers Paradise", you'll be able to stroll to nearby restaurants, cafes, museums, parks and Old Port. Then, return to a relaxing space that you'll be very happy to call 'home'!

Clean & Safe Apt w/Parking-Close to Downtown

Your cute, cozy one bedroom apartment is close to all that Portland has to offer! Your home away from home, you have 1 GBPS Wifi, the fastest Portland offers along with a comfortable desk to work from. Centrally located, the space it is a short drive to all of the great restaurants, bars, shops, parks and more! It is close to the 295-N ramp (Freeport outlet shopping is just a few exits down).Our location blends city living with that “just-off-the-beaten-path” feel that offers pleasant rest.

Waterfront Private Apartment only 5 min to LLBean!

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 8 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

Cozy 3BR | Pet Friendly | Near Portland | Parking

This 3-bedroom apartment in a quiet Westbrook neighborhood offers a bright, pet-friendly stay just 15 minutes from downtown Portland. With a full kitchen, private workspace, and plenty of natural light, it’s a great fit for families, professionals, or small groups. Key Amenities: • 3 queen beds + queen air mattress • Full kitchen • Smart TV, board games, and books • In-unit washer & dryer • 1 full bathroom • Keurig • Free driveway + street parking • Pet-friendly • Smart lock entry

Beautiful Home In Gorham Maine

Well appointed, bright and sunny apartment for two people in a quiet neighborhood. Large private back yard, formal gardens and pond, elevated deck, well stocked kitchen. 25 mins. to downtown Portland and the seacoast area. Minutes to local nature trails, swimming, kayaking, dining, supermarket & bakeries. ** NO PROFILE/REVIEWS? please provide a little info about whose coming, ie, name/age/occupation, reason of visit, etc, and any other info you wish to provide. Thank you!

Inn@Norwood large private 2 br suite

3rd floor walk-up large 2 br suite all yours Spacious lr/dr kitchenette no range/oven or large fridge Private bath hispeed wifi secluded relaxing deck quiet neighborhood contact host for very reasonable off-season student/visiting professional rates Public trans plentiful safe street parking great restaurants parks close-by downtown Portland bus/train station airport colleges 2 mile walk or short ride Come to the Inn to relax in privacy enjoy your event & explore Maine

Lily Brook Farm, Hollis, Maine

I’ll respond to inquiries after June 26, 2025 One bedroom apartment on horse/sheep farm in Hollis, Maine. View of farm from living room, bedroom on second floor up very steep farm stairs. One Queen comfy bed. There is a day bed in the living room. 21 miles from Portland and Kennebunkport. The farm is on rt 35. Cars can go by fast, they always break the speed limit. Lots of peace out the back door but be aware this is not way out back away from the road.

Rustic charm close to Portland

Peaceful and private. My home is a country getaway with unique charm and has a feeling like no other. Just voted the safest town to live in Maine, located close to downtown Portland, the Portland Jet Port, Freeport, beautiful Maine beaches, apple orchards, a Gorgeous wedding venue a mile away called Caswell Farm and close to trails for hiking, my home has many options. It's a great spot for a group of 6 or a couple of 2 to unwind.

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 when needed. Please, no smokers, kids under 13, or guest pets. STHR-000718-2018