Pet-friendly holiday rentals in Chebeague Island

Walk to Everything!

Our location is fantastic! From here, walk to restaurants, shops, the beach, everything! We have ample parking, too. We ask guests to keep in mind that this is an older home, last remodeled in 1969! Please consider this when booking, while staying, & when reviewing. While the location can't be beat, expect to be staying in an older home if you choose our place. Due to COVID-19, please bring your own towels, sheets & pillows. We provide bedspreads. ALLERGIES: A dog & cat lived here recently.

Cottage style home 2 blocks from the beach!

Comfortable Cottage style home with 3 bedrooms, private baths. Many amenities. Two living areas for everyone's comfort, a beautiful kitchen, a large private outdoor patio with multiple seating, a fire pit and a gas grill. Backyard is partially shared. We are close to the Portland nightlife, airport, shopping, restaurants and family-friendly activities. We are in a community that offers biking , running routes, parks and History. Warm, welcoming home. In law attached with private entrance.

Haven on the Hill

Registration #2018-4091. On top of a quiet, leafy street in Portland's East End, our hippest neighborhood! Short walk to popular destinations like the Old Port, the ferry terminal, breweries and award-winning restaurants...plus water views, sea gulls, fog horns, running trails, sunrises and sunsets! NOTE: Please *do not book this space* if you can't honestly live by our House Rules. All guests must confirm that their group will abide by House Rules w/in 24 hours of booking to be confirmed.

Tranquility, Relaxation, Family, Romance

Bring your family or have a romantic getaway in this beautiful 2 bedroom, 2 private baths located in this quiet country setting. Pet friendly. Big fenced in wooded back yard for your pets to roam. Big back yard deck w/ seating, grill. Minutes away to boat launching area to rent party boats, kayaks, paddle boats, Swimming, winter sports on Milton 3 ponds. Seasonal blueberry, peach, apple picking in town. Park your boat or snowmobile trailors. Skydive New England right in town. Fall leaves.

Pet-Friendly Cottage in OOB

Welcome to our inviting pet-friendly cottage nestled in Old Orchard Beach! Perfect for up to 5 guests, this cozy retreat features a warm living space, a well-appointed kitchen, a grill, and an electric outdoor firepit among many other amenities. With comfortable sleeping arrangements, a modern bathroom, and a fenced yard for your furry companions, it's an ideal spot for a coastal getaway. Located a short walk from beach and attractions it is sure to be a memorable stay!

Historic charm, Modern amenities, Walk downtown

Newcastle historic district charm, modern amenities, walking distance to restaurants. Fast Wi-Fi, A/C, great bathroom, full laundry and kitchen plus two bedrooms with queen beds. Pet friendly and handicap accessible, single floor design with parking right in front. Ideal for a MidCoast escape or remote work change of scenery. Three individually adjustable heat pumps in each of the bedrooms and the main living space provide cooling and heating for four season pampering.

The Farmhouse at The Cross Farm

1910s farmhouse less than a mile from Mt. Abram main lodge, and 6 miles from Bethel and Sunday river. 3 private bedrooms sleep up to 6, with one full bath (with tub) on the first floor and a small half bath on the second floor. First floor laundry room. A back deck off of the kitchen has seating and a gas grill. Large full eat-in kitchen. Access to 80 acres (for walking and biking, but no motorized off-road vehicles are allowed), and approved pets are welcome!

Studio w/ Patio, Sauna & Onsite Massage

Cozy daylight basement studio in the center of Rosemont. Relax with your own private patio, sauna, on-site massage & facial. Just minutes to Portland's extensive trail system. Delicious restaurants and markets within a short walk and just 2.5 miles from the historical Old Port and artsy downtown! Perfect for business and leisure! Conveniently located just 10 minutes from the Portland Jetport and less than five minutes from I-295 and I-95. STHR-000170-2018

Captain Cookie's sea cottage

It’s the most wonderful type of the year in Maine. The leaves are red, the crowds are gone, the lobsters are still fresh. The suite is newly renovated with off street parking and a private entrance - Pet friendly! We have all the amenities you’ll need for your vacation including heatpumps in each room as the nights get colder. Set in a peaceful neighborhood, 10 mins to beach, 15 to pier and Old Orchard street. Off leash allowed at all times on the beach!