A calm lake with a buoy in the center, surrounded by a dense forest and a misty shoreline.

Waldoboro Vacation Rentals

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Waldoboro vacation rentals

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a round rug.

1. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
3.0 star property
Waldoboro
10.0 out of 10, Exceptional, (2 reviews)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
United States
Deborah
$450 nightly
The price is $491
Sep 9 - Sep 10
Total with taxes and fees
Near Lakes, Bay & Trails! Historic Waldoboro Gem
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a round rug.

2. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
Waldoboro
9.8 out of 10, Exceptional, (27 reviews)
"It was a wonderful stay at this home. The home was incredibly clean, the beds were very comfortable and had great bedding on them. It was a great location to all the nearby places we wanted to go to. Loved the historic charm. We would love to come and stay again!"
United States
Tina S.
$461 nightly
The price is $502
Sep 9 - Sep 10
Total with taxes and fees
Near Lakes, Bay & Trails! Historic Waldoboro Gem
A two-story white building with green shutters, a central entrance with columns, and a brick chimney.

3. The Entire Waldoboro Inn

The Entire Waldoboro Inn
Waldoboro
$1,180 nightly
The price is $1,286
Sep 7 - Sep 8
Total with taxes and fees
The Entire Waldoboro Inn
A modern living room with a large window, a wooden ceiling, and a view of a green landscape.

4. Come Spring Farm Airstream , Lake & farm animals

Come Spring Farm Airstream , Lake & farm animals
Union
8.0 out of 10, Very Good, (4 reviews)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
$249 nightly
The price is $271
Aug 27 - Aug 28
Total with taxes and fees
Come Spring Farm Airstream , Lake & farm animals

5. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (464 reviews)
"Great stay, great location."
United States
Jerold
$150 nightly
The price is $163
Sep 1 - Sep 2
Total with taxes and fees
Trade Winds on the Bay
A living room with a fireplace, a mounted TV, and bookshelves filled with books.

6. “Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
9.8 out of 10, Exceptional, (46 reviews)
"We loved our cozy stay everything was clean and tidy, and we had everything that we needed"
United States
Betty Jo O.
$371 nightly
The price is $405
Aug 27 - Aug 28
Total with taxes and fees
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
A grassy yard with a small table and chairs, a house, and a lake in the background.

7. Rustic Retreat Across from Lake; Family Friendly!

Rustic Retreat Across from Lake; Family Friendly!
Union
8.8 out of 10, Excellent, (22 reviews)
"Great location for visiting the coast."
United States
Sallie S.
$368 nightly
The price is $401
Aug 30 - Aug 31
Total with taxes and fees
Rustic Retreat Across from Lake; Family Friendly!
A grassy yard with a small table and chairs, a house, and a lake in the background.

8. Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
8.0 out of 10, Very Good, (3 reviews)
"The cottage is cute with a great view of the lake. Quiet and peaceful yet convenient to town. Plenty to see and do in the area. We had a wonderful time and I highly recommend staying here!"
United States
Lorraine
$358 nightly
The price is $391
Aug 30 - Aug 31
Total with taxes and fees
Rustic Retreat Across From Lake; Family Friendly!
A spacious living area with a wooden ceiling, a dining table surrounded by chairs, a red leather sofa, and a view through large windows.

9. Quiet & Lovely Lakefront Cottage for Families!

Quiet & Lovely Lakefront Cottage for Families!
Union
9.8 out of 10, Exceptional, (16 reviews)
"Evocative of my youth and going to the family lake camp in the summer. We had great weather and a great time. The cabin is a ‘Mainer’s’ memories wrapped in eclectic reminders. What a joy!"
United States
Venise B.
$470 nightly
The price is $512
Aug 27 - Aug 28
Total with taxes and fees
Quiet & Lovely Lakefront Cottage for Families!
A dome-shaped building at night with a visible interior light source.

10. Dome 1 - Luxury Dome at Come Spring Farm

Dome 1 - Luxury Dome at Come Spring Farm
Union
9.6 out of 10, Exceptional, (19 reviews)
"Scenery was amazing, it was a bit chilly at night but a great place for peace and quiet!"
United States
Maurice E.
$303 nightly
The price is $327
Sep 1 - Sep 2
Total with taxes and fees
Dome 1 - Luxury Dome at Come Spring Farm
A spacious tent with a large skylight, a bed, a sofa, a lamp, and a fireplace.

11. Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
8.6 out of 10, Excellent, (14 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
$238 nightly
The price is $257
Aug 27 - Aug 28
Total with taxes and fees
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
A wooden deck with Adirondack chairs and a grill.

12. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
8.8 out of 10, Excellent, (10 reviews)
"This place was nice and clean. The only thing was the service was spotty and WiFi was slow. Overall, great place and great location."
United States
Alexis H.
$252 nightly
The price is $275
Sep 1 - Sep 2
Total with taxes and fees
Bright 2-Bedroom Apartment Near Downtown Thomaston
A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

13. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (51 reviews)
"We loved our stay here! Check-in was easy and the host was responsive!"
United States
Jessica H.
$286 nightly
The price is $312
Sep 22 - Sep 23
Total with taxes and fees
2 Bedroom Close to Town Home
A spacious living room with a black leather sofa, a glass coffee table, and large windows offering a view of greenery.

14. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (38 reviews)
"Great Stay!"
United States
Pastor Heidi G.
$304 nightly
The price is $331
Sep 15 - Sep 16
Total with taxes and fees
Peaceful, Centrally Located Home with Seasonal River Views
A bedroom with a bed, a bedside table, and a window with curtains.

15. Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
9.0 out of 10, Wonderful, (8 reviews)
"Location was perfect and Lynn was so helpful. We’d definitely stay here again!"
United States
Caycee A.
$183 nightly
The price is $199
Sep 2 - Sep 3
Total with taxes and fees
Peaceful Intown Studio ~ Walk to Shops & Dining
A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

16. Simplicity-Just what you need! STR24-20

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (31 reviews)
"Very nice tiny house in a quiet neighborhood. Easy walk to downtown"
United States
sarah
$150 nightly
The price is $164
Sep 15 - Sep 16
Total with taxes and fees
Simplicity-Just what you need! STR24-20
A modern kitchen with a central island, built-in appliances, and a dining area with a high chair.

17. Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Thomaston
10.0 out of 10, Exceptional, (39 reviews)
"Great place at a great price! I look forward to staying there again. "
United States
Stephen H.
$455 nightly
The price is $495
Aug 30 - Aug 31
Total with taxes and fees
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
A pond surrounded by trees, with two wooden chairs facing the water.

18. Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
Lincolnville
7.6 out of 10, Good, (15 reviews)
"The cabin is exactly as advertised. The dogs were happy there and we enjoyed our stay. "
United States
Becki C.
$146 nightly
The price is $159
Sep 3 - Sep 4
Total with taxes and fees
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine
A patio with a round glass table and two chairs, overlooking a grassy area with trees.

19. Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
8.0 out of 10, Very Good, (11 reviews)
"Great stay! Pet friendly, super responsive host and excellent location!"
United States
Cassie M.
$150 nightly
The price is $163
Aug 27 - Aug 28
Total with taxes and fees
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
A kitchen with a large island, two bar stools, wooden cabinets, a red refrigerator, and a view of the outdoors through large windows.

20. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
$252 nightly
The price is $266
Aug 31 - Sep 1
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 5
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Waldoboro Hotel Reviews

Smuggler's Cove Inn

Smuggler's Cove Inn

10/10 Excellent
"The view from the rooms was beautiful. Atmosphere was relaxing. Would recommend for anyone to stay."
Michael 2-night trip
Posted 13 hours ago
Smuggler's Cove Inn

Find out more about Waldoboro

Everything you need to know about Waldoboro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Waldoboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Waldoboro vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Waldoboro vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Waldoboro. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Waldoboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Waldoboro rentals

At Expedia, we put the best Waldoboro vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Waldoboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Waldoboro vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Waldoboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Waldoboro?

Yes, there are vacation rentals in Waldoboro close to Morse's Sauerkraut, or you can go with a secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the gardens in Waldoboro. Make sure you have time to check out the local tours and bars during your trip.

What are some of the best vacation home rentals that Waldoboro has to offer?

Comfortable, Close to Town Home, with Oceanview.: This vacation home rental outside Waldoboro offers a patio, a private yard, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Waldoboro?

With 21 Expedia vacation rentals, you're sure to find just the right place for your Waldoboro stay.

What’s there to see and do in Waldoboro?

Pemaquid Pond and Duckpuddle Pond are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Morse's Sauerkraut. In the larger area, you’ll find Fawcett's Antique Toy and Art Museum and St. George River.

What’s a vacation rental in Waldoboro like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Waldoboro. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a family trip or a small group gathering.