Pet-friendly vacation rentals in Westport Island

This home is amazing! It was perfect for our group of ten family members that were in the area to celebrate a wedding for the weekend. Our hosts could not have been more accommodating and we were so impressed with their hospitality!! So many nice touches and such a spacious, comfortable home - no detail overlooked. Enjoyed our stay immensely and would definitely return.

This was our first experience with an Air B&B and happy that it was with Spencer. Our main reason for the East Coast trip was to see our grandsons football games at Bowdoin College and it was a perfect location. We stayed for seven weeks and loved the experience.

I was looking for a small, waterfront place to stay with my dog to decompress and unplug. OakLeaf exceeded my expectations and was perfect. Sunrises and sunsets overlooking the river and sitting by a fire were spectacular and I stayed an extra night. Bill, his wife, and their dog Shadow were gracious hosts and knowledgeable about the area. I will be returning!

Stayed with my wife and 2 year old son for a full week. Wonderful location walking distance to many shops, bakeries, restaurants etc. Blackout curtains in the bedroom were helpful for our son with naps and early sunrise. Playground a 30 second walk down the street which we used often. Private parking space directly behind the home was also convenient. We thought it was great value for the location and a nice alternative to booking an apartment or larger home when we spent the majority of our trip out exploring. Overall, we were very pleased with our experience.

Second stay at the farm house. Two weeks this time. We just love it here. Plenty of space yet cozy, everything you need, lovely outdoors space. We enjooed watching the chickens, dicks and horse next door. I wish we could stay for months. Thank you, Amy and family!

We absolutely loved our stay! We rented the house for 7 adults and 1 dog to celebrate a 31st bday! We loved being able to walk right down to the tasting room for a beer, cook a big dinner in the kitchen, play games, and watch the amazing vcr collection. Everything was clean and comfortable. So glad it’s a dog friendly space!

Katrina's home is always clean and welcoming. The living room (TV area) is comfortable. The dining room table a nice work space if you need to 'work from home' while in her home. The additional half bath on the first floor - a great addition. I am already considering when we will return !

Great location, easy walk into town. Lovely place. on arrival had an issue with heat but Melanie responded quickly and we were able to rectify the problem quickly. Would definitely stay again. The dog enjoyed also!

Thank you for allowing us to stay at your beautiful home. The photos did it no justice! I can’t wait to be back, we will be stay here again.

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!

The perfect place for a weekend away with friends! Easy to find/get to, and less than 15 minutes from downtown Portland! The house was extremely clean, well stocked with anything you might need, comfortably furnished, and looked just like the listing. Susan was extremely responsive and helpful! Highly recommend, and we can’t wait for our next stay here!

My stay was very comfortable. The property was well kept and updated. The beds and furniture were were in perfect condition. Both the house and the grounds were exceptionally clean and well maintained. I would visit again!

BEAUTIFUL Home!! Tons of space to relax and spread out with our family! The beds were very comfortable! We really appreciated all of the bathrooms for our group! The kitchen was huge and so handy for preparing meals! I absolutely loved the style and atmosphere of this wonderful home! We also loved being able to bring our dogs!! We had a lovely time and we would most definitely come back!!! 🥰

Katherine was the perfect host. Super responsive and accommodating with check in-check out times which was so appreciated. This was my second stay here and I am sure I will be back. Clean and cozy!

Was a very nice peaceful getaway the home was spotless and had everything we needed plus extra great place to disconnect

My wife and I spent 2 nights here while traveling Maine. It was very relaxing and exactly what we needed towards the end of our trip. It was unlike anything I’ve ever experienced but I would absolutely do it again! We also fell in love with this restaurant down the road called “Farmhouse Beer Garden”.

Our family and I had a wonderful stay at Jackies, we are all originally from maine, and her home gives you everything great about maine. We really felt at home, it snowed christmas eve which made it even more beautiful ( The driveway was plowed out early as well). I brought a small christmas tree with us on our trip up, and when we walked in, the place was decorated for christmas, which was just amazing and so thoughtful. We definitly plan on staying again, the next time we are back in maine. Thank you again Jackie!

We thoroughly enjoyed our stay at Samantha's place in Cushing. To say that she is "very responsive" would be an understatement. She typically responded within 10 minutes no matter what my question was. She lives a short distance away which really helped facilitate things. We had a minor issue with the Internet which required communication with the service provider, but she coordinated everything and resolved it right away. The house is totally charming - old, a bit creaky and adorable - and well maintained (no issues there). We imagined how great it would be to visit in wintertime and snuggle up to a roaring fire. They have an expansive yard with gardens great for a short evening stroll. Forest habitat behind the property was great for bird watching. The area is absolutely beautiful - quintissential coastal Maine. The Olson House (local attraction) is a few minutes drive from the house. The grounds have a walking trail along the water with fantastic views of the coast.

Keith's place was such a cozy stay! The facility was spacious and well-ventilated. Keith was helpful, and the kitchen was equipped with items to cook with. Would love to stay again! The neighborhood cats are very friendly, I enjoyed interacting with them and giving them treats!

Margaret’s place is very homey with all the necessities for a family gathering. The neighborhood is beautiful and close to beautiful trails

Elizabeth was a wonderful host and her home is perfect for a peaceful, relaxing vacation. The house was spotless, well appointed, and very cozy. The short walk to the beach and town market is really convenient. Her rental is a perfect home base if you’re visiting Portland or exploring the Maine coast nearby.

Host was great and friendly. Beautiful neighborhood. Apt was very clean and comfortable. Many extras like Keurig, coffee, tea hot chocolate and water bottles. Cozy extra blankets, fans and fireplace. Bathroom was clean and had liquid soaps, shampoo etc. Not a full kitchen, but all you need. Would definitely stay again.

Lori’s place felt like a home away from home. The apartment was bigger than we expected with beautiful furnishings and built-ins. The kitchen was amazingly well stocked making it easy to cook meals with ingredients from Pat’s Meat Market a block away. Noble Pizza is also not to be missed.

Amazing $1M+ house. Everything you need, especially in the kitchen. Everything is high-end and perfect. Beautiful house and land. Great deck with fire table. Upstairs shower is amazing! Left doggie treats for my Labrador! The property is on the water; the house is on the hill, so it is a steep hike down to the river. Beautiful Maine woods surrounding the house. It is private, no neighbors to worry about. This host has made this house a dream vacation home with everyone one would possibly need. Farmer’s markets are close by, as well as Freeport and LL Bean. Couldn’t recommend more!