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Waldoboro vacation rentals

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Top-rated vacation rentals in Waldoboro

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

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Rental unit in Rockport

4.96 out of 5 average rating, 263 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.

Rental unit in Edgecomb

4.91 out of 5 average rating, 322 reviews

Sunny Apt in Woods 10 Min to 3 Towns- Dog Friendly

Bright, cozy apartment, surrounded by deep woods, completely separate from our home, w/ its own entrance, yet we are available if you need us. 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 - peaceful woods, but less than 15 minutes from restaurants, shops & activities, plus, dedicated WiFi /2 Smart TVs. While dogs are welcome we can’t host feline guests due to allergies.

Guest suite in Rockland

4.98 out of 5 average rating, 406 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

Yurt in Appleton

4.96 out of 5 average rating, 216 reviews

SILVER MOON, a Yurt for All Seasons

Silver Moon at The Appleton Retreat is quite private, check out the Trail Map. This contemporary yurt features a private therapeutic hot tub on the wrap around deck, a fire pit, and fast wifi. Silver Moon is located in a wooded area close to a bog that attracts a variety of wildlife. 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.

Cottage in Edgecomb

4.97 out of 5 average rating, 232 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.

Guest suite in Damariscotta

4.94 out of 5 average rating, 182 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.

Rental unit in Damariscotta

4.93 out of 5 average rating, 183 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.

Rental unit in Damariscotta

4.92 out of 5 average rating, 279 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.

Cottage in Union

4.93 out of 5 average rating, 102 reviews

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.

Place to stay in Owls Head

4.98 out of 5 average rating, 211 reviews

A comforting sweet off grid cabin near the beach!

Get away from it all when you stay at our sweet little off grid cabin in the woods. A place where sleep and peace meet! Surrounded by 15 acres of woods and fields and within walking distance to Birch Point State Park, you'll have a perfect little getaway - all while being only a few minutes away from Rockland.

Vacation rentals for every style

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Hotels

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Unique stays

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Popular amenities for Waldoboro vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Waldoboro's top sights

Moody's Diner37 locals recommend

Morse's Sauerkraut30 locals recommend

Beth's Farm Market25 locals recommend

Odd Alewives Farm Brewery22 locals recommend

Damariscotta Lake State Park13 locals recommend

Sterlingtown Public House11 locals recommend

Other great vacation rentals in Waldoboro

Home in Nobleboro

5 out of 5 average rating, 83 reviews

Country home ~ Family friendly

Cottage in Whitefield

4.96 out of 5 average rating, 74 reviews

Ollie's Cottage on the Sheepscot River

Home in Waldoboro

5 out of 5 average rating, 59 reviews

Renovated 1911 Farmhouse on Peaceful Peninsula

Home in Waldoboro

4.96 out of 5 average rating, 47 reviews

Long View Farm on Broad Bay

Treehouse in Georgetown

4.98 out of 5 average rating, 423 reviews

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Guest suite in Thomaston

4.95 out of 5 average rating, 73 reviews

Midcoast Retreat with Fireplace Near Downtown

Cottage in Farmington

4.98 out of 5 average rating, 138 reviews

The cottage at Marble Farm.

Guesthouse in Newcastle

4.98 out of 5 average rating, 88 reviews

Modern Hillside 1 BR near Damariscotta/Newcastle

Quick stats about vacation rentals in Waldoboro

Total rentals
80 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
2.9K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

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 20 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 10 house rentals with air conditioning in Waldoboro. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Waldoboro have wireless internet?
Absolutely! We offer over 30 house rentals with wireless internet 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 10 homes with air conditioning, over 20 homes with a bbq area, over 30 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

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