
Holiday houses in Waldoboro
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Top-rated holiday rentals in Waldoboro
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Loon Lodge
Located on beautiful Damariscotta Lake, "Loon Lodge" is a rustic cabin from another era. Fall asleep to the sound of crickets and frogs and wake every morning to the call of the lake's many loons. The cabin is 30 minutes from Augusta and 15 minutes from Damariscotta. Hiking enthusiasts will enjoy climbing the Camden Hills-a quick 45 minute drive from the lake. You’ll love my place because of the views, the ambiance, the people, and the location. My place is good for couples and solo adventurers.

BREEZE, in a tree The Appleton Retreat
BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Moss House: A Modern Waterfront Cabin in the Woods
Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Look! River Run Cottage on tidal salt waterfront
Maine the way life should be is not just an expression at River Run its a way of life. Located in Andrew Wyeth country (town of Cushing, Maine) River Run is a recently renovated 600 square ft cottage 75 ft off the St George river. It sits on 260 feet of privately owned tidal salt water river frontage just miles upriver from the Atlantic Ocean. Great for a romantic get away or to reconnect and recharge. Spend your time on the shore or sight seeing in the near by towns of Rockland and Camden

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba
Waterfront Retreat with Gorgeous Views Stunning 3-bedroom, 2-bath home perfect for multi-generational gatherings. Features an open-concept layout, chef’s kitchen, 1st-floor bedroom and bath, 2nd floor with 2 bedrooms and 1 bath. Kayak from your backyard, hike nearby trails, or swim in Damariscotta Lake just a 5-minute walk away. Stay connected with high-speed fiber optic WiFi. Close to charming Newcastle and Damariscotta shops and restaurants. A true oasis for nature and relaxation lovers!

Renovated historical Waterfront farm
28 acre property is a Forever Farm surrounded by rolling hills and Lake frontage . This farm is also referenced in the historical book “ Come Spring “ we purchased this beautiful property in 2019 and have spent the last year renovating it. Our favorite part of the home are the floor to ceiling windows overlooking the round Pond . This is very peaceful retreat. On a daily basis , you can pick your own fresh eggs from coop and feed our pigs . We are 15min to Camden ,Rockport , Rockland .

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.

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

The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Timeless Tides Cottage
This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

1830s Cape hosted by George & Paul
This 1830 cape is for rent by the month or weekly or for a two-night minimum stay. It is located at the edge of the historic village of Waldoboro. It offers a convenient base to sightseeing in midcoast Maine. It’s old-fashioned, decorated with plants, antiques and paintings and features a large, fully equipped kitchen, music room with piano, television room with pull-out sofa, full bath with stall shower and outside patio. Your hosts are right across the driveway.

"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.
Popular amenities for Waldoboro holiday rentals
Stay near Waldoboro's top sights
Other great holiday rentals in Waldoboro

5BR Hilltop Retreat | Gather & Explore Mid-Coast

Coastal Farmhouse for Families | HotTub + Firepits

Studio with Fireplace-Walkable to Downtown

Peaceful Intown Studio ~ Walk to Shops & Dining

The "Fish House": Salt Water Cove Carriage House

Four-Season Luxury Lakefront Cabin Close to Camden

Seal View Cottage

Coastal 4BR Farmhouse w/ Water Views, Walk to Town
When is the best time to visit Waldoboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $301 AUD | $286 AUD | $276 AUD | $288 AUD | $291 AUD | $329 AUD | $334 AUD | $329 AUD | $322 AUD | $278 AUD | $365 AUD | $344 AUD |
| Avg. temp | -6°C | -5°C | 0°C | 6°C | 12°C | 17°C | 21°C | 20°C | 16°C | 9°C | 3°C | -2°C |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Waldoboro?
Four-legged friends are welcome in Waldoboro. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Waldoboro?
Yes! Work meets play with ease at over 30 vacation rentals in Waldoboro featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly house rentals in Waldoboro?
Waldoboro has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in cabin rentals in Waldoboro?
Experience the best of Waldoboro with our cabin rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Waldoboro have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Waldoboro. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Waldoboro have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Waldoboro. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Waldoboro have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Waldoboro. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Waldoboro?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with wifi, over 10 homes with a bbq area, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Waldoboro

Total holiday rentals
Explore 90 holiday rentals in Waldoboro

Nightly prices starting at
Waldoboro holiday rentals start at $72Â AUD per night before taxes and fees

Verified guest reviews
Over 3,490 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
70 of Waldoboro holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Waldoboro rentals

4.9 Average rating
Waldoboro stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a washing machine and dryer Waldoboro
- Rentals with a fireplace Waldoboro
- Rentals with a kayak Waldoboro
- Waterfront rentals Waldoboro
- Rentals with beach access Waldoboro
- Rentals with a fire pit Waldoboro
- Rentals with a patio Waldoboro
- Pet-friendly rentals Waldoboro
- Rentals with lake access Waldoboro
- Rentals with outdoor seating Waldoboro
- Family-friendly rentals Waldoboro
- House rentals Waldoboro
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