Holiday houses in Waldoboro

4.92 out of 5 average rating, 119 reviews

Guest suite in Warren

Private Guest Suite in Midcoast Maine

Newly redecorated in 2024! A spacious, serene & private guest suite room with original details, private bathroom & king bed. In a historic Sea Merchant's house, this can be your home base as you explore the Midcoast & Penobscot Bay. Take a short drive to the surrounding coastal villages of Camden, Rockland, Damariscotta & more. Situated on a quiet road, 2 min. drive from Rt 90 (less traffic) & Rt 1, which will take you up & down the lovely coast of Maine. See our guidebook for recommendations!

4.92 out of 5 average rating, 183 reviews

Apartment in Nobleboro

Finding Joy

This lovely apartment is above our garage. You can come and go as you please. We have created a place for peace and solitude. Sit on the deck or look out the dining room window and see the woods and wait for the birds and wildlife that may be wonder through the yard. There is coffee and tea available, along with basic breakfast supplies, if you wish. Keyless entry allows for you to come anytime after check-in. Please note, you have to be comfortable with stairs to access the apartment.

4.98 out of 5 average rating, 440 reviews

Guest suite in Rockland

5 Laurel Studio private entrance STR20-69

Open concept small studio, private patio and entrance, full kitchen. *SHARED wall between studio and main house, therefore some shared noise. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes to the Farnsworth and CMCA museums, Strand Theater, restaurants, antiques shops & galleries. ALSO NOTE we do not have television. We have wifi but you must bring your own device . EXEMPT FROM ACCEPTING SERVICE DOG

4.85 out of 5 average rating, 518 reviews

"Ship Shape": waterfront, cozy studio- downtown

Located in a historic 200 year old building "Ship Shape" is close to downtown but on a quiet tree-lined residential street. It is just one block to the library, bookstore, post office and all the lovely shops. It is on the shore of the Damariscotta River with wonderful views from inside and out.. You’ll love my place because of the neighborhood, the light, the outdoor space, and the comfortable bed. My place is good for couples and solo adventurers.

4.83 out of 5 average rating, 222 reviews

Dome in Union

Dome 4 at Come Spring Farm

Our geodesic domes sit in on 10 acres of our property . In total come spring farm is 28 acres , you will have access to round pond to kayak , fish or swim. You may also visit the Alpacas , bunnies , pigs , sheep and our new lounge area opening June . The bathroom facilities are private for each dome, no sharing .You will need to walk to bathhouse . Pocket WiFi can be provided if requested . Follow us on IG at Comespringfarm .

4.98 out of 5 average rating, 106 reviews

Guesthouse in Newcastle

Modern 1-BR I Wooded Retreat I Mid-Coast Maine

Escape to your perfect Midcoast Maine base camp—just 5 min to Damariscotta/Newcastle & 1 hr 6 min to PWM. Enjoy forest views, modern comforts, and easy access to the coast. • King bed + ensuite • Fully equipped kitchen + charcoal BBQ • Vaulted ceilings, wall of windows, open layout • Private deck, fire pit • WiFi, laundry, parking • Generator (2024) for year-round comfort Ideal for foodies, outdoor lovers & oyster fans!

4.92 out of 5 average rating, 203 reviews

Mystical Mary Howe Room, Downtown Damariscotta

This spacious studio apartment is perfect for relaxing after a day of exploring beautiful Damariscotta and surrounding communities. Situated on the third floor of one of Damariscotta's many historical buildings this apartment consists of a large living room area with kitchenette and a separate large bedroom with bath. Parking is right next to the building and a key will be provided for your apartment.

4.92 out of 5 average rating, 286 reviews

Fernald's Backside

Fernald's Backside is a sunny, comfortable 2nd floor apartment , tucked behind S. Fernald's Country Store in the heart of downtown Damariscotta. It features a deck with views of the Damariscotta River and Harbor. A one bedroom apartment with ample living space and full kitchen, it can sleep 5 with a double and single bed and a sleeper sofa. Fernald's Backside is Pet free.

4.92 out of 5 average rating, 110 reviews

Cottage in Union

Cozy Lakeside Getaway | Seven Tree Cottage

This newly renovated, cozy getaway is an ideal escape for a couple, small family or friends. Less than 20 minutes from the charming oceanside towns of Rockland and Camden, the cottage is named after Seven Tree Pond, offering guests waterfront views in the winter, with lake access (boat launch, picnic area, and swimming access) less than a 5 minute drive.

4.82 out of 5 average rating, 142 reviews

Cottage in Rockport

Cozy Cabin in MidCoast, Maine

Our adorable little cabin comes with a working fireplace, washer/dryer, flatscreen tv, internet, full kitchen and more! Conveniently located between Rockland and Camden, this spot offers nearby hiking, beaches, shopping, golfing and restaurants. We are tucked right off Route 1 and are minutes from the Samoset Resort and Breakwater Lighthouse.

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Other great holiday rentals in Waldoboro

4.91 out of 5 average rating, 57 reviews

Guesthouse in St. George

Timber frame studio on the ocean

ChristineRating, 5 stars8 months ago

Had such a nice long weekend here! The views from the studio out over the water are perfect for morning coffee and the place felt rustic and clean. Quiet neighborhood with some great places for pictures and The Grange, which has music and Fall craft fairs walking distance from the studio. The best food is in Rockland or Thomaston. I enjoyed the Waterworks and Ancho Honey restaurants. Parking around town is easy and (usually) free! Camden is also really pretty and historic and is nearby. Enjoyed my stay! Thank you :)

4.97 out of 5 average rating, 64 reviews

Guesthouse in Jefferson

Oasis Family Farm Near Hidden Valley

NathanRating, 5 stars2 weeks ago

Absolutely loved staying here. They really have a wonderful setup, and the hosts are incredibly friendly, as are all of the animals on the farm. One of the best Airbnbs I’ve ever stayed in, hands down.

4.82 out of 5 average rating, 45 reviews

Cabin in Union

Private cabin on the Saint George River

NataliaRating, 5 stars2 weeks ago

Loved her place!! Was an amazing getaway for me and my kids, my toddler loved the bed being up high! The amenities were all spot on! The fire pit, kitchen supplies, bathroom, beds. And is walkable to the town area, with coffee shop and restaurants. The river sound to sleep was great!!!

Home in Waldoboro

4.84 out of 5 average rating, 190 reviews

Thistledown Farm's Pennysworth - An 1800's barn.

EstherRating, 5 stars4 months ago

We really enjoyed our stay at Penny’s house! The barn is absolutely beautiful. Please be aware that this is not a private home, even though it’s listed as such. Penny is clear in the description that she lives on the ground floor, and the kitchen and living room are shared spaces. That being said, if that’s what you’re expecting, this is a charming stay and a great base point for exploring the area. Our dog had an absolute blast playing in the yard and we deeply appreciated Penny’s hospitality.

Place to stay in Waldoboro

4.91 out of 5 average rating, 53 reviews

Cookhouse Loft. A suite of rustic accommodations.

LynnRating, 5 stars6 days ago

Laura's space was relaxing, casual and inviting. I came to attend my cousin's wedding and would have liked to spend more than just a few days! Laura is a font of local information and suggestions. An absolutely lovely person. If you are lucky, she might even invite you to one of her delectable chef tasting tables. The outside is just ablaze with flowers and the property is charming with a culinary garden, fruit trees and a wonderful babbling brook. What a treat to fall asleep to the sound of it. Waldoboro offers a peaceful, small town feel and offers many walkable options. An adorable coffee shop and local tavern are just a block away. The Waldo Theater is just across the street and famous Moody's diner is a few short blocks. If I can offer one small nugget of input, I would have liked to have a full length dressing mirror in the bedroom. If you are coming to the midcoast for an event, weekend getaway, hiking or tourism, I recommend the centrally located Cookhouse Loft!

4.96 out of 5 average rating, 23 reviews

Home in Georgetown

Breathtaking Bay Views!

ColletteRating, 5 stars8 months ago

I can’t say enough about what a nicely appointed home in a beautiful setting this is. I came for peace and tranquility and it did not disappoint. I haven’t had such good sleep in over 2 years. Highly recommend and plan to return next year! Thank you all so much for sharing your lovely home.

4.99 out of 5 average rating, 94 reviews

Deluxe Midcoast Maine Retreat

EdwardRating, 5 stars4 days ago

We have enjoyed the stay at Patricia’s place. It’s well designed and decorated. It’s cozy and yet fully functional. Patti is super nice and we had a wonderful conversation about Damariscotta. We would strongly recommend Patricia’s place anyone who should have chance to visit Damariscotta.