Pet-friendly holiday rentals in Cumberland County

Our son, his girlfriend, my husband and I enjoyed staying at the cottage in late October 2024. The location was quite scenic as it overlooked Casco Bay, near Portland, ME. The host made suggestions that we followed (bringing firewood & blankets). The kitchen was equipped with utensils & coffeemakers. The neighborhood was quiet. We enjoyed walking in the local preserve along the water and took advantage of visiting the Portland Museum of Art and eating at The Honey Paw, an Asian fusion restaurant.

This is the 2nd time I've stayed at Emma's place. I came both times for a workshop and ceremony that took place in both Freeport and in Portland. Drives to Portland were the longest, and not too taking, and I chose to stay at Emma's place BECAUSE of the way the house holds me: the spaciousness, the attention to art and wisdom, the lighting and unfussy-yet-design-inspired furniture choices, the plant life, the textures and colors: all these things are soothing and welcoming. It was a pleasure to drive "home" exhausted, knowing what it feels like to open that back door.

Lovely house for our weekend getaway to Maine!

Kevin's place worked really well for my two dogs and myself. There is a fenced in back yard. I liked the setup of the primary bedroom with the attached full bath and laundry. Comfortable bed! Very quiet neighborhood and very convenient to access other areas of Portland. I really appreciated the back deck setup. I need to find the comfy chair they have out back for my own home! Clean and usable kitchen. Nice stack of Maine materials and recommendations for local items to check out. Overall, a very pleasant stay, thank you!

Had a short but lovely stay here. Awesome location and Kathleen was very responsive and gave us great recommendations. Only wish we had planned to stay longer!

My wife, myself and our pup loved our time at Christine’s. Thought it was a great value for the area and we appreciated how many little extras were included (snacks, beer, wine, seltzer, toiletries). Location is great for walks to East Prom or Old Port, and parking is a breeze with the dedicated driveway. It is a cozy fit if you’re a bigger person (I’m 6’ and I had just a few inches of clearance from the ceiling).

This cottage is perfect for Sebago if you own a boat. She has everything you could need for a stay on the water. I would love to stay here again this year.

We had family in town for graduation and Amy’s place checked all the boxes for us. Plenty of room to spread out yet still be together. The bedrooms were roomy and cozy. Our little nephew loved the well-stocked bookcase that allowed him to have a different story every night. The trampoline and outside space were wonderful. We even used the barbecue. Would definitely recommend!

Great backyard with a pool, hot tub, fire pit and privacy with the woods.

Heather is a wonderful host and this cabin is a lovely place to stay

We would 100% recommend Dina’s place to ANYONE (and we hope to be back)! The place is beautiful and would accommodate a small to large family. The pool and hot tub are incredibly nice and peaceful surrounded by trees. The furniture is incredibly comfortable and the kitchen great to use. Dina is also incredibly thoughtful and quick with her replies. We got a little turned around arriving at night (the GPS lead us up the road a bit), but we found it!

Gorgeous house, peaceful area, a great back deck with pool and hot tub! Jey was a great host, very helpful and quick response time. The house was very clean and put together. I would totally recommend staying at jeys house!!

Beautiful Airbnb! Everything in the Airbnb was very well thought out. The host was super nice and always quick to respond. My only regret was not spending more time here!

Christina’s place is awesome! Cozy, centrally located on the island, and stocked with everything you need for a great stay. We were very comfortable! Loved the afternoon sun on the back deck and having a fire pit out front in the evening. A bonus that it’s dog friendly! Christina was very responsive and helpful. We hope to be back again!

this house was perfect for a girls weekend getaway!! spacious and beautiful, still super close to all the activities in portland, but wonderfully peaceful! it was too cold to use the pool but it looks great and I would love to book this house again later in there summer to be able to use it! the beds were super comfortable and easy off street parking. thanks for a great stay!

We had a wonderful stay in Angela’s beautiful home. It had great amenities, was super clean, and had everything we needed. Loved the pool and fire pit. The kitchen was roomy for cooking too. 5 stars!

Central location, but was surprisingly very quiet and private. Kelsey is an excellent communicator and host.

Cody is the greatest host. He was very genuine, and responsive with everything. This little home will be one to remember. It was very comfortable and peaceful. I would come back again! 😊🙏🏽

This lovely property was perfect for us. The host really knows how to “think like a guest” and has anticipated what will make you feel comfortable and at home with numerous little extras. The apartment is beautifully decorated and the bed and furniture were comfortable. Will definitely book on our next visit.

We really enjoyed our stay here! It was close to Caswell farms which we were at for a wedding. Alison was so kind and helpful. She went above and beyond to make sure we had what we needed! Would absolutely stay here again.

Laura was a great host. We stayed at her place for a night to split up our drive from MA to Bar Harbor. We almost didn’t want to leave! Very clean, comfortable and easy check in. Laura was also super helpful and responsive and even gave us a great list of things to do in Acadia. We 100% recommend her and her place, you won’t be disappointed!

We had a very relaxing stay at Carl & Rose's place. It was a very cozy space on a rainy fall weekend. Lots of fleece blankets, pillows and tea made us feel warm and welcome. The oversized reclining couch and 4-poster bed were super comfy. The height of the bed was a bit intimidating at first but quite luxurious once you sink into the soft supportive mattress. Great home base for exploring the beautiful scenery of Maine and nearby NH, especially with the leaves in full color.

The views were amazing and the place was perfect! They’ve thought of everything (beach chairs, extra linens, coffee) and the flowers and birds make the property even more lovely. I stayed with my daughter and there is privacy within the space. The beach is a five minute walk from the house. We will definitely stay again!

Lovely cozy cabin! I went mid-May, which probably isn’t the best time if you want to enjoy local activities. But it is a good time if you want to just relax at the cabin. The host were really nice and accommodating. Would definitely stay again.