Holiday rentals in Waldoboro

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Top-rated holiday rentals in Waldoboro

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

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Top guest favourite
The exterior of a converted barn is showcased, featuring a spacious backyard with lush green grass and several trees. A deck is visible on the upper level, while a playground structure and a long log add elements for outdoor leisure.
Home in Nobleboro
5 out of 5 average rating, 102 reviews

Country home ~ Family friendly

Our converted barn is located on a little used road with easy access to miles of trails. Our road is little used but intersects with US 1.There is a downstairs bedroom with an open loft on the second floor. Wonderful light and views. A fire-pit, swings, hammocks, and playground structures make this a perfect place to stay with your family. A peaceful place to visit for all ages. World famous Moody's diner, a grocery store and gas stations etc. are just 3 miles away! Perfect for young children.

Top guest favourite
A cozy sitting area features a comfortable couch adorned with various cushions in shades of blue and brown. A small table with a decorative item and a candle stands beside a potted plant, while natural light filters through sheer window coverings.
Flat in Thomaston
4.9 out of 5 average rating, 192 reviews

A cute little gem in down east Maine

It’s a cozy, private and calm space. Kind of “quirky artsy zen”. *Please note that there are steep stairs inside the apt. **Also stairs leading up to deck/door. *We are on route one/Main st. This is a BUSY road. FYI :) Guests say that the space is quiet. The location is convenient. 15 -20 minute radius to all the down east attractions. There are parks to walk dogs nearby. Laurels bakery is 2 minute walk down theThe downtown has restaurants, general store, coffee and art- to name a few!

Top guest favourite
A bright eat-in kitchen area features a small wooden table with two chairs. Natural light streams through large windows, providing a view of the lush garden. A washer and dryer are positioned nearby, enhancing the functionality of the space.
Flat in Bath
4.96 out of 5 average rating, 161 reviews

1820s Maine Cottage with Garden

Enjoy a cozy shipbuilder's cottage in Bath, Maine. This quaint apartment attached to a family home has its own entrance and contains a bedroom, a bathroom, a kitchen, and a living room with antique details that reflect its 200-year old history. Only a 15-minute walk to historic downtown Bath, a 3-minute drive to Thorne Head Preserve, and a 25-minute drive to Reid State Park and Popham Beach. Come appreciate everything MidCoast Maine has to offer! PLEASE NOTE: This apartment has steep stairs!

Top guest favourite
A bright living area is visible, featuring a light-colored sofa and a comfortable armchair. A wooden dining table with two chairs occupies the foreground. Windows allow natural light to illuminate the space, while soft curtains frame the views of the surrounding forest.
Loft in Edgecomb
4.92 out of 5 average rating, 367 reviews

Cozy Forest Loft (15 min to 3 cute towns)

Bright, cozy loft, surrounded by deep woods, a tranquil retreat offering true peace, separate from our home, w/ its own entrance; we're here if needed. Located between Boothbay, Damariscotta, & Wiscasset, 1 mile from Route 1 and 27, on 13 acres, abutting 100s of acres of preserve land - provides the best of both worlds - woods rich with abundant birds, but less than 15 minutes from restaurants, shops & activities, plus, dedicated WiFi /2 Smart TVs. Dogs welcome, no cats due to allergies.

Top guest favourite
A charming red house is visible from the winding driveway, framed by tall trees and patchy grass. The front porch runs along the house, while two garage doors and a wooden structure are located nearby. A dog can be seen walking along the pathway.
Flat in Nobleboro
4.92 out of 5 average rating, 210 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 favourite
A charming yellow house features white trim and a welcoming front door. Flower boxes are filled with vibrant blooms beneath the windows, surrounded by a neatly tended garden. A stone wall provides a defined border, enhancing the inviting exterior.
Guest suite in Rockland
4.98 out of 5 average rating, 472 reviews

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

Top guest favourite
The exterior of the cottage features a large screened-in porch framed by tall trees. A pathway leads to the entrance, while colorful shrubs and a pumpkin add seasonal charm. The serene waters of the Sheepscot River are visible in the background.
Cottage in Edgecomb
4.98 out of 5 average rating, 341 reviews

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

Top guest favourite
A spacious guest room features a king bed with a soft quilt and several plush pillows. Original details are highlighted by a decorative fireplace surrounded by tile. Natural light fills the room, complemented by light-colored walls and elegant wall sconces.
Guest suite in Warren
4.92 out of 5 average rating, 150 reviews

Private Guest Suite in Midcoast Maine

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!

Guest favourite
A dining area is illuminated by natural light, featuring a dark wooden table with a decorative centerpiece of fruit. Large windows offer a view of the water and nearby boats, while comfortable seating is arranged alongside the table.
Home in Cushing
4.93 out of 5 average rating, 162 reviews

Dockside Retreat - Winter Openings

This beautiful, newly renovated home is three bedrooms and two bathrooms, with an open living and dining room waiting to give your family or group of friends the ideal Maine vacation experience! On site parking, a lovely yard, a new sauna on a beautiful deck overlooking the water, nearby fields and steps away from the famous Olson House on one side, you can sit on the deck and overlook the working lobster wharf with fishermen coming and going daily on the other side!

Top guest favourite
The exterior of a charming yellow house is presented, featuring white stairs leading to a green front door with an ornamental design. Lush shrubs frame the entrance, and tall trees provide shade to the vicinity, creating a welcoming appearance.
Home in Waldoboro
4.99 out of 5 average rating, 105 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 favourite
A spacious studio apartment features wooden paneling and warm lighting. A queen bed with white linens is flanked by two bedside tables with lamps. A small breakfast nook with a checked tablecloth is visible, along with a desk and wooden chair.
Guest suite in Damariscotta
4.93 out of 5 average rating, 243 reviews

Cozy Carriage House in Downtown Damariscotta

Welcome to Damariscotta, Maine! Our carriage house apartment has the rustic, romantic feel of a classic Maine cabin, but is located a short walk from downtown Damariscotta. Guests have a private studio that includes sleeping accommodations, a bathroom, a small kitchen area, and closet space. This is the perfect spot for adventurous travelers who want to explore the Midcoast of Maine like a local or for creative folks to unplug and focus on their craft.

Top guest favourite
Three colorful flower pots are displayed on a blue wooden surface. The left pot features pink flowers, the middle pot has yellow blossoms, and the right pot showcases soft peach-colored blooms. Lush greenery can be seen in the background, creating a serene outdoor setting.
Flat in Searsmont
4.98 out of 5 average rating, 176 reviews

Searsmont Studio

Fight inflation with a reasonably priced Maine vacation. Low prices, excellent value. Check our ratings. Peak Foliage Oct. 14-20 Entire studio efficiency apartment w/ private entrance above our garage. Fully furnished, including washer and dryer. Country setting on quiet road. Starlink High Speed WiFi/Satellite TV, full kitchen. gardens, lawns and picnic table. Close to Camden, Rockport and Belfast, but in the country.

Popular amenities for Waldoboro holiday rentals

When is the best time to visit Waldoboro?

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Avg. price£154£146£141£147£149£168£171£168£165£162£136£146
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Frequently Asked Questions

  • 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 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.

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

    Experience the best of Waldoboro with our house rentals, starting at about $80 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 a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in Waldoboro. Enjoy a tailored experience with all the comforts you desire.

  • 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.

  • 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.

  • What are the most popular amenities for House Rentals in Waldoboro?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a bbq area, over 20 homes with air conditioning, over 30 homes with wifi, 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 £37 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    70 of Waldoboro holiday rentals include wifi 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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