
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.

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.

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.

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.

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!

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!

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 .

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.

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

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.

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.

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

Private 1 BR Apt - 3 mi to town

Spruce Ledge | coastal. sauna. retreat.

The Maine Frame: Modern A-Frame Cabin | Freeport

More Boathouse than Lakehouse

Coastal Farmhouse for Families | HotTub + Firepits

Thistledown Farm's Pennysworth - An 1800's barn.

Waterviews + Sunsets + Gardens Aglow

Mill Retreat
When is the best time to visit Waldoboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ771 | ﺩ.ﺇ735 | ﺩ.ﺇ709 | ﺩ.ﺇ738 | ﺩ.ﺇ746 | ﺩ.ﺇ845 | ﺩ.ﺇ856 | ﺩ.ﺇ845 | ﺩ.ﺇ826 | ﺩ.ﺇ815 | ﺩ.ﺇ683 | ﺩ.ﺇ735 |
| 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 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 ﺩ.ﺇ184 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 & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 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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