Townhome holiday rentals in Portland

Family Ready Home Close to Town Trails and Outlets

This gorgeous townhouse that is just steps away from North Conway, walk to the Muddy Moose for dinner and drinks. Every smart device you can think of has been thought of, less than 5 minutes to Cranmore, the outlets for shopping, 15 minutes to Attitash, tons of trails for hiking, mountain biking, cross country skiing, snowshoeing. Three full bathrooms, three queen beds, 2 single beds. WIFI, cable, 70 inch TV set up for gaming, foosball table, three levels of space so everyone can spread out.

Cozy, Private Beach House minutes from the ocean

Family-friendly Beach House - Old Orchard Beach - Quick walk to attractions (beach, amusement park, shopping & restaurants) Experience one of Southern Maine’s premier destinations from the comfort of a newly remodeled cottage-style home, tucked away on a quiet, tree-lined street. Just a short walk or bike ride to Old Orchard Beach Pier, our cozy home offers all the trappings of a perfect family vacation: shopping, restaurants (we hope you like fresh lobster!), an amusement park and the beach.

HistoricWestEnd 3StoryBrickTownhouse WalkToAll 5*

In historic West End. Central Walk to all. quiet 3 story brick townhouse. Winding stairs connect third floor bedroom,Living room and view, to 2nd flr King bed, open loft then first floor living room and kitchen. 2 full Bathrooms. Privacy within house, French doors open kitchen to cedar deck, stainless BBQ & "secret garden” below. 3rd floor living room/ bedroom are bright & sunny. 2nd Flr bathroom is a unique marble plaster wet bath, with turn of the century nickel hardware and a great shower.

Perfect for multiple families- central location!

Spacious 4 story townhouse with 2 separate living rooms in perfect location for all of your favorite valley activities. 2 min to Cranmore, 5 min to outlets, 10 min to Storyland. Highlights of property include vaulted ceilings, large shared backyard, large stone wood burning fireplace, fully stocked kitchen, 3 private decks, and laundry room. For your convenience, we have many games, toys, and books for all ages, pack & play, 2 highchairs, bedrail, and baby gate. Brand new linens provided.

Modern Victorian

This is a beautifully renovated, private, 2 bedroom, first floor of a duplex. The yard is fenced in and has a large deck. The unit is very light and bright and tastefully decorated. The rooms are very large and the kitchen is open to the living room. It is in a quaint little village with a little country store just steps away where you can find almost anything you need! Please note that one building in particular is not attractive. Once inside.the fenced in yard, it is not visible.

2BR Townhouse on Westbrook

Forget your worries in this spacious & serene space. This ultra quiet neighborhood offers a peaceful retreat from bustling city life. The tree-lined streets create a perfect setting for leisurely strolls or morning jogs. The absence of heavy traffic & urban noise makes this property a haven for those seeking a calmer environment. The property is mint & serves as the perfect home away from home. Close to downtown Westbrook, 5-mins to 95, 6-mins to airport & 15-mins to downtown Portland.

4 Bedrooms! 7 Beds! 2 Full Bath. Free parking

Sunny large 1500 sq foot first floor Condo in a charming Portland neighborhood. Centrally located. Walk to Rosemont Market & Bakery, Rwanda Bean coffee & more. Five minutes to Rock Row, Five minutes to Thompson's Point / Bissell Brothers and 10 minutes to the Old Port. All are welcome! - Sleeps 12 to 14! -5 queen beds and 2 sofa beds. - Free Parking! -Smart TV -Fully equipped kitchen - Smart lock self check in! - A/C units in every bedroom and living room from 6/1 to 9/15

Great get away spot,historic home in Kennebunkport

Located 1.8 mi-dock square, 2.6 mi- Colony Beach, .7 mi -Cape Arundel Golf Course. Plenty of onsite parking, beach pass provided for Kbunk Beaches, a large back yard for fun and relaxation. Just on the outside of town in a country setting. Comfortable setting for relaxation. This is a daily reservation from Oct.1st-June. I love to make sure my guests have as much fun as they can while they are visiting and will help out in anyway possible. No dogs of any kind are allowed

Captain Fuller House: Boat Builders Retreat - Main

Wake up to sweeping views of Linekin Bay at this pet-friendly coastal retreat . Nestled in a quiet neighborhood, the home sleeps 6–8 guests with three bedrooms and two full bathrooms, perfect for families or small groups. Enjoy peaceful waterfront scenery, fresh ocean air, and easy access to Boothbay Harbor. Modern comforts include an on-site EV charger, while classic Maine charm makes it an ideal place to relax, recharge, and enjoy life by the bay—paws included.

Oasis in East Bayside —2 bedroom home

Just a short walk from fabulous restaurants, breweries, and the beach, I love living in this vibrant neighborhood. My home has a kitchen (help yourself to necessities!), dining area, and living room. On the second floor there are two bedrooms and a bathroom. There’s a lovely yard with a table and chairs and a private driveway to park. You’ll have the whole place (and won’t be contributing to Portland’s housing crisis by choosing this owner-occupied spot!).

Retreat at Sea Cloud Cottage in Historic Wiscasset

Welcome to Sea Cloud Cottage - A Charming Retreat in Wiscasset, Maine Sea Cloud Cottage is a beautiful one-bedroom home, once the guest house to the larger Acorn Cottage next door. Perfectly designed for a couple or small family (with an extra child or adult on the pull-out sofa), this 900-square-foot gem offers an inviting, comfortable space for your getaway. You can also rent it alongside Acorn Cottage for larger parties, accommodating up to 9 guests.

3 Bdrm 2 Ba Contemporary Townhouse

Gracious living Room with gas fireplace. Well stocked contemporary kitchen. Three bedrooms, 2 baths, 5 mins from the Old Port. Two excellent ethnic restaurants around the corner. Also a friendly local dive bar with great bar food. Bedrooms - 1 queen bed in each, air conditioned. Common areas all yours! Very quiet and private. Off street parking for one car. Plenty of free, safe parking on the road. A $5-8 cab or Uber ride to Old Port.