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 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
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 410 reviews

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.

Top guest favourite
An open living area features a dining table surrounded by black metal chairs, with a cozy sofa nearby. Large windows allow natural light to fill the space, showcasing green walls and a neutral rug. Decorative elements add character without overwhelming the tranquil ambiance.
Apartment in Rockport
4.97 out of 5 average rating, 313 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.

Guest favourite
A welcoming living area features light-colored walls adorned with framed artworks. A potted plant adds a touch of greenery while a floor lamp stands in one corner. The staircase leading to the upper level is visible, providing access to the bedroom and bathroom.
Apartment in Thomaston
4.9 out of 5 average rating, 191 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 serene waterfront view captures calm waters reflecting the sky and surrounding landscape. Lush greenery is visible along the shore, while scattered clouds drift across the blue sky. The tranquil scene invites relaxation and appreciation of nature.
Home in Newcastle
4.99 out of 5 average rating, 179 reviews

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!

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, 365 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.

Superhost
Floor-to-ceiling windows frame a serene view of rolling hills and water, allowing natural light to illuminate a cozy seating area. A small wooden chair sits outside, complemented by a soft, draped blanket on a nearby couch.
Farm stay in Union
4.86 out of 5 average rating, 174 reviews

Newly renovated home on 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 .

Top guest favourite
A modern cabin exterior showcases a deep blue facade and a welcoming entry, highlighted by a wooden deck adorned with an outdoor seating area. The surrounding landscape features various plants and autumn decor, enhancing the serene setting within the woods.
Tiny homes in Appleton
4.96 out of 5 average rating, 115 reviews

Little Apple Cabin on 5 acres, amazing stargazing!

Cabins don't come much cuter than Little Apple Cabin. It's as if someone stayed here and *then* invented the word 'CabinCore'. Nestled in the magical woods of Midcoast, Maine, this cabin is the perfect getaway. Located just 25 minutes from the coast, it's the perfect spot for exploring all that the midcoast has to offer. 20 minutes to Camden and Rockland, 25 minutes to Belfast. (No hunting allowed). Surround yourself by the forest, stargaze all night, and rejuvenate in nature.

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, 469 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, 333 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
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, 104 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
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.
Apartment in Searsmont
4.98 out of 5 average rating, 174 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 vacation rentals

When is the best time to visit Waldoboro?

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Avg. price$290 CAD$276 CAD$266 CAD$277 CAD$280 CAD$317 CAD$321 CAD$317 CAD$310 CAD$306 CAD$256 CAD$276 CAD
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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 air conditioning, over 20 homes with a bbq area, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Waldoboro

  • Total vacation rentals

    Explore 90 vacation rentals in Waldoboro

  • Nightly prices starting at

    Waldoboro vacation rentals start at $69 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,490 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    70 of Waldoboro vacation 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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