
House holiday rentals in Waldoboro
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Top-rated house rentals in Waldoboro
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Popular amenities for house rentals in Waldoboro
House rentals with a pool

Luxe Liberty: Getaway with Heated Indoor Pool!
This is everything you could ask for and more. Shops and downtown life are within 30 minutes and you get the peace and quiet of a getaway without needing to go anywhere if you don’t want to. The hosts were great and the town is quaint. I highly recommend to any family who wants to relax, unwind, and disconnect from the hustle and bustle of everyday life.

The Boathouse at Spruce Harbor
My return visit to the Boathouse was even lovelier than I hoped it would be. The location can't be matched by anything else I've seen. I enjoyed a September visit with my dog and was lucky to have pristine weather. I lived a very simple and healthy outdoors life and came home the better for it. The Boathouse is true to its description: it is simple and rustic and uncomplicated but well-equipped, and is perfect for one-and-dog, or for two people. A little coming-and-going from the neighboring houses meant that I didn't feel isolated. Margaret is truly an exceptional and friendly host who communicates promptly and clearly. I almost hesitate to share "my" Boathouse location with too many of my back-home friends because it feels so intimate and special. I already want to be back there. I offer my deep thanks to Margaret and to the place that I could - briefly - call home.

House in the woods
Booked this place for our anniversary to get away from the city for a weekend.. we found exactly what we were looking for! The hot tub was wonderful, the house was clean and cute, and we had everything we could have needed! Estelle was very responsive and gave clear instructions for everything. Would recommend this place for a quiet getaway or a small group trip in the summer!

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
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!

Dog Friendly Midcoast Cape
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!!! 🥰

There's No Place Like Home
Kathi’s place was great! Super close to the Downtown Portland/Old Port area. Kathi was a great host, extremely responsive and genuinely nice, plus she even made my family and I some delicious blueberry muffins for our stay! Her instructions were clear and she made us feel right at home! Would definitely stay again whenever we’re in the area!

The Hill's on Buttonwood
Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown

Dreamy Indoor Pool/Hot tub/Sauna Near Beaches
Thank you for a great couple of days in Portland! The house is close to everything while still being far enough away to unwind. We loved coming back from dinner and ending the night in the pool/hot tub. And our dog loved the fenced in backyard; he finally got the hang of the doggie door on the last day :). Thanks to Alexa for being super responsive and providing some great local recommendations!
Weekly house rentals

New cottage just steps from beach
This was our second year staying at Don’s and it was great as always! Beautiful space, clean, updated, and well stocked kitchen/linens. Location to the beach can’t be beat and all the beach things you’d need are available for use. Don and Sue are both wonderful and we look forward to future stays.

Cozy & quiet on the river... the Captain's House
The hosts were very prompt in communicating. The thoughtfulness they have put into furnishing the property is amazing. It has a very vintage nautical feeling to it. The house is extremely well appointed. We didn’t have any problems at all. The surroundings are off the beaten path which we especially appreciated. It’s a short 10 minute drive to Damariscotta Downtown. I would highly recommend this property.

Adorable Beach House Across the Street From Beach!
Even though we only stay for one night it was amazing! Loved the spaces look and coziness, the beds where pretty comfortable we went during the winter so the bedrooms got a little chilly but nothing a Mainer isn’t used too :) we loved the couch and living room it was big enough for 8 of us to fit comfortably! The beach is walking distance we had so much fun walking the beach and then coming back and enjoying our night! Over all beautiful and comfortable satay!

137 Shore Road Ocean Point view now with WiFi
Jerry's house was a great location with terrific views. The house was tastefully decorated and immaculate. A perfect Maine getaway that we cannot wait to go back to in the future.

Oceanfront, Mere Point year round home Brunswick
Loved the layout of the house. Great kitchen and master bedroom. Master bath a little cramped. Enjoyed the view and outdoor seating.

Cozy Cottage With River View
Jeremy and Ellen are fantastic hosts. Very communicative during booking and prior to arrival with suggestions of what to do (we were travelling from the UK). We stayed for 16 nights and the house felt like home - it has everything you need. Absolutely fantastic place to stay and we really recommend it.

Entire House in Portland!
Ned and Rachael were incredible hosts. They made us feel special for the weekend and were extremely responsive and respectful of any requests we had. The place is absolutely beautiful with comfortable beds, and the location is close to downtown. This was my second time staying here and it was great each time!

Charming Belfast home. Walk downtown/water
Erica and Jack’s Belfast home is a charming place close to a little rocky beach area and walkable to Main St. It’s in a very good location. We have relatives in town who we were able to visit easily. The owners are responsive during and after booking, and have provided good info about the area prior to checking in. It’s self check-in and we felt safe and comfortable the second we entered their rental. Everything is very clean. The kitchen has all cooking essentials and even some pantry items. They have a large sized fridge perfect for grocery/snack items when you have kids with you. The beds are comfortable, enough blankets, towels, and washcloths to use. Bathroom in the main bedroom. It’s a nice cozy place to stay in for a few days. 💛
Private house rentals

Cove House
We have been going to this area of Maine for over fifty years. I found this gem several years ago and haven’t stayed anywhere since. I find it to be peaceful, walkable to the center via footbridge, it’s all that we want. Kathy is a great host, quickly responds to any questions or needs you may have. We always know we will have a great experience staying here.

Kirby Island Road Retreat
Loved staying at this cabin! I was a last minute booking and the hosts were super nice and accommodating. Would recommend these hosts and this cabin to everyone!!

Oceanfront Luxury Estate in Mid-Coast Maine
This was such a wonderful property for my family -- beautiful and peaceful with lovely views. We loved spending our days out in the spacious yard, playing lawn games, sitting around the fire pit, and fishing, and eating all our meals out on the patio. Everyone left feeling very relaxed and happy. Thank you Pam and David for sharing your home!

4bed Full House on Private Dr. w/ Large Yard
This is an amazing place to stay, especially for families! Destioney is quick to respond and both understands and anticipates the needs of her guests. I absolutely recommend this home and hope it's available in the future when we return to Belfast. 5/5

Distinctive Home & Garden
My friends and I traveled to Portland, ME for a book club trip and we were so lucky to have found Marie’s house. We had an incredible stay at her peaceful home. The location was serene, providing a perfect escape from the hustle and bustle of everyday life. The house was spotless, well-maintained and had all of the amenities we needed for a comfortable stay. Marie was a wonderful host, she was very attentive, left detailed instructions and recommendations. I highly recommend this home to anyone looking for a relaxing, worry-free getaway!

Beautiful Coastal Maine Getaway
The house is beautiful and close to the city of Portland. Everything was clean. The sheets and linens were visibly clean and smelled fresh which is always appreciated. Great place to stay

Modern & Sunny East End House. Private Parking!
Jennifer’s place was great. So bright, clean and cheerful. Clearly thoughtful and welcoming to guests. The beds were very comfortable. The place was walking distance from so many great restaurants and coffee spots. Jennifer was great about communicating with us before and after our stay. Even reaching out to us when we forgot something there. We appreciated the hospitality and very much enjoyed our stay! We would love to stay again sometime soon.

Sweet home away (pet friendly)
The house was really well updated and decorated and setup in a way that was easy to move in and settle for the week. Everything was easy to find and the details were all thought through, the bottle of water on the night stands was a nice touch. The communications were straight forward and easy to follow. The house is lovely backing up to a small stream.
Quick stats about house rentals in Waldoboro
Total rentals
30 properties
Nightly prices starting at
£60 before taxes and fees
Total number of reviews
980 reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Fox Ridge Golf Club
- Brunswick Golf Club
- Popham Beach State Park
- Belgrade Lakes Golf Club
- Pemaquid Beach
- Samoset Resort
- Maine Maritime Museum
- Wolfe's Neck Woods State Park
- Pemaquid Point Lighthouse
- Pinnacle Park
- Spragues Beach
- Coastal Maine Botanical Gardens
- Narrow Place Beach
- Bear Island Beach
- Sand Beach
- Falmouth Country Club
- Lost Valley Ski Area
- Andrews Beach
- East End Beach
- Head Beach
- Mile Beach
- Pebbly Beach
- Hunnewell Beach
- Bradbury Mountain State Park