Vacation rentals in Waldoboro

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Top-rated vacation rentals in Waldoboro

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Apartment in Rockport
4.97 out of 5 average rating, 330 reviews

The perfect getaway - Camden/Rockport/Rockland

Bayview Suite is the perfect getaway! Centrally located in Rockport, allowing easy access to Camden, Rockland & Bar Harbor. Country living, yet close to downtown (2.5 miles) without the busy traffic and noise. Located on 20 acres with farmland and live stock surrounding this peaceful and beautiful property. Fresh local farm stands within walking distance. Mountain bike trail on property to reach the area ski lodge & swimming pond. Great for swimming, boating, fishing, biking, hiking & skiing.

Top guest favorite
Guesthouse in Cushing
4.97 out of 5 average rating, 111 reviews

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

Top guest favorite
The exterior of a vibrant orange building is shown, featuring a covered porch with a welcome sign. Lush greenery and flowering plants surround the entrance, while a pebbled pathway leads to the door, creating an inviting approach to the accommodation.
Apartment in Washington
4.99 out of 5 average rating, 103 reviews

The Adams Suite on U-pick Blueberry Farm

Our one-hundred acre farm is located in the small rural village of Washington. It is located just 2/10 of a mile from the village center where the general store, village church, library, and town offices are located. Beautiful Washington Pond boat landing is only 4/10 of a mile away. Easy commute East (30 minutes) to the coast and must see towns of Rockland, Rockport and Camden or West (30 minutes) to our capitol Augusta. One hour and forty minutes to Bar Harbor and Acadia National Park.

Top guest favorite
An exterior view displays a newly constructed set of wooden stairs leading to a deck above. The stairs are framed with pale wooden railings and are flanked by a red building. The sky is bright with scattered clouds.
Apartment in Nobleboro
4.92 out of 5 average rating, 213 reviews

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.

Top guest favorite
Guesthouse in Warren
5 out of 5 average rating, 9 reviews

Meadow Breeze cottage

Our peaceful 16 acre wetland meadow/ wooded property is teeming with birds and wildlife, wild cranberries, and a short trail system making this a perfect place to relax and enjoy nature year round. Seasonal access to the St. George River and White Oak Pond, allow for paddling May to October. We are just 3.5 miles from historic Union Common, the oldest Common in Maine, and 1/2 mile from Beth's Farm Market, featuring baked goods, fresh produce, milk, and fall activities in season!

Guest favorite
A spacious house is set on a well-manicured lawn, surrounded by trees. The building features a wide porch with two turquoise chairs facing a garden, while large windows illuminate the interior. A gentle slope leads to the surrounding greenery, creating a peaceful environment.
Apartment in Waldoboro
4.96 out of 5 average rating, 27 reviews

Farmstay private entrance

Relax at this peaceful place to stay. There is no kitchen, but there is a small fridge, a microwave, and a coffee maker. If you are a spinner, or want to learn, please join us for Fiber Sunday 1 - 3 each week this summer. Enjoy the charisma of this old farm. It is a quiet place to to come after a sightseeing day, with a private porch. The bedrooms are located upstairs. Our living space is downstairs. There are 70 acres of fields and woods here with walking and riding trails.

Top guest favorite
A wooden staircase leads up to a cozy loft above a barn, framed by natural wood siding. A small deck with chairs is visible, offering a view of the clear blue sky and surrounding trees, connecting the indoor space with the outdoors.
Guesthouse in Damariscotta
4.96 out of 5 average rating, 116 reviews

Private tree-top loft 5 minutes from Damariscotta.

Relax in this cozy loft with a light-filled deck overlooking the woods, but just five minutes to downtown Damariscotta. This brand new loft above our barn is cozy with all you need for a perfect vacation. You can relax with your morning coffee above the trees. It has an indoor toilet, sink and breakfast bar and outdoor shower. We’re a semi-retired couple and love to share our 62 acres property with stream and meadow. There are quite a few stairs to the loft.

Top guest favorite
An open-concept great room features high wooden ceilings with exposed beams. Large windows provide ample natural light and views of the surroundings. A comfortable seating area includes a sofa and coffee table, while a dining space with chairs is positioned near the kitchen.
Cottage in South Thomaston
4.96 out of 5 average rating, 203 reviews

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.

Top guest favorite
Home in Waldoboro
4.99 out of 5 average rating, 106 reviews

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.

Top guest favorite
A private therapeutic hot tub is situated on a spacious deck, surrounded by lush trees and a serene natural landscape. Nearby, a gas grill is positioned for outdoor cooking, complementing the tranquil ambiance of the outdoor space.
Yurt in Appleton
4.95 out of 5 average rating, 369 reviews

SNOW SWEET, A Yurt for All Seasons

Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Top guest favorite
A modern post and beam home is viewed from a distance against a night sky filled with stars and the Milky Way. The structure features expansive balconies, with warm light spilling from the interior, creating a welcoming atmosphere in a peaceful, natural setting.
Guest suite in Rockland
4.97 out of 5 average rating, 199 reviews

Salty Dog Hilltop Guest Suite (permit #STR26-57)

This guest suite is located in the lower level of our NetZero post & beam home which sits on a mountain overlooking the Penobscot Bay. The over 600 sq. ft. large open floor plan is spacious & clean with a large private patio. The location is quiet and peaceful while only 5 minutes from the action in downtown Rockland and only 15 minutes from Camden. This is a great home base to explore all that the Midcoast area has to offer.

Top guest favorite
Apartment in Waldoboro
4.92 out of 5 average rating, 64 reviews

Cookhouse Loft Waldoboro/ Suite of rustic lodging

Stay in our centrally located loft that historically doubled as a dance venue as well as an Army post. Walking distance to coffee, bar, hiking, library, theatre and restaurant Full commercial kitchen coupled with large private bed and bath, cathedral ceilings and original art. Cool and eclectic. Private entrance. Fun for artists,foodies and garden buffs and those ok with stairs. Not for children.

Popular amenities for Waldoboro vacation rentals

When is the best time to visit Waldoboro?

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Avg. price€183€172€161€173€175€198€201€198€194€167€220€207
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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Waldoboro?

    Four-legged friends are welcome in Waldoboro. Choose from more than 30 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 vacation rentals in Waldoboro?

    Waldoboro has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Waldoboro?

    Experience the best of Waldoboro with our house 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 house rentals in Waldoboro have wifi?

    Absolutely! We offer over 30 house 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 30 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 vacation rentals in Waldoboro

  • Total vacation rentals

    Explore 80 vacation rentals in Waldoboro

  • Nightly prices starting at

    Waldoboro vacation rentals start at €43 per night before taxes and fees

  • Verified guest reviews

    Over 3,420 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Waldoboro vacation 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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