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

Waldoboro Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Waldoboro vacation rentals

Outdoor dining

1. Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
Waldoboro
The price is CA $203
CA $253 total
includes taxes & fees
Oct 25 - Oct 26
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
A two-story white building with a symmetrical facade, large windows with shutters, and a central entrance with a door and columns.

2. The Entire Waldoboro Inn

The Entire Waldoboro Inn
Waldoboro
The price is CA $991
CA $1,514 total
includes taxes & fees
Oct 26 - Oct 27
The Entire Waldoboro Inn
Lobby sitting area

3. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (522 reviews)
"Everything was clean, easy check in process and convenient location, walking distance to multiple restaurants."
United States
Bill
The price is CA $153
CA $167 total
includes taxes & fees
Nov 3 - Nov 4
Trade Winds on the Bay
A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

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

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (37 reviews)
"This was such a super cute place. Great little get away. Very clean! I would definitely recommend this place if you are in the area!"
United States
Beth
The price is CA $136
CA $212 total
includes taxes & fees
Nov 2 - Nov 3
Simplicity-Just what you need! STR24-20
A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

5. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
8.8 out of 10, Excellent, (58 reviews)
"It was in a perfect location for our planned trip. Thank you"
United States
Nita S.
The price is CA $161
CA $363 total
includes taxes & fees
Nov 2 - Nov 3
2 Bedroom Close to Town Home
A bedroom with a bed, a bedside table, and a window with curtains.

6. Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
9.0 out of 10, Wonderful, (12 reviews)
"Great location, excellent accommodations, perfect for our weekend adventure."
United States
Brian
The price is CA $203
CA $252 total
includes taxes & fees
Oct 29 - Oct 30
Peaceful Intown Studio ~ Walk to Shops & Dining
A wooden deck with a glass door leading to a room.

7. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
9.0 out of 10, Wonderful, (6 reviews)
"Great location awesome place to take it easy for a few"
United States
Gene
The price is CA $120
CA $289 total
includes taxes & fees
Oct 26 - Oct 27
Tiny Cottage Near Everything 10
A modern living room with a large window, a wooden ceiling, and a view of a green landscape.

8. Come Spring Farm Airstream , Lake & farm animals

Come Spring Farm Airstream , Lake & farm animals
Union
8.4 out of 10, Very good, (5 reviews)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
The price is CA $231
CA $359 total
includes taxes & fees
Oct 25 - Oct 26
Come Spring Farm Airstream , Lake & farm animals
A spacious tent with a large skylight, a bed, a sofa, a lamp, and a fireplace.

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

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
8.8 out of 10, Excellent, (16 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is CA $231
CA $335 total
includes taxes & fees
Oct 26 - Oct 27
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
A two-story house with a front porch, a garden with various plants and a stone pathway leading to the entrance.

10. Rockland is the arts capital of Mid Coast Maine! STR 26-36

Rockland is the arts capital of Mid Coast Maine! STR 26-36
Rockland
9.6 out of 10, Exceptional, (117 reviews)
"Lovely accommodations."
United States
Eric V.
Rockland is the arts capital of Mid Coast Maine! STR 26-36
A living room with a fireplace, a mounted TV, and bookshelves filled with books.

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

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
10.0 out of 10, Exceptional, (51 reviews)
"We loved everything about this place! It’s beautifully decorated and feels like a home away from away. The host was wonderful and made it easy to communicate with her. The view from the deck is so pretty! I loved having a cup of tea out there and looking at the water. It was a perfect spot! We are so grateful!"
United States
Rhiannon A.
The price is CA $258
CA $491 total
includes taxes & fees
Oct 26 - Oct 27
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
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
9.2 out of 10, Wonderful, (16 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.
The price is CA $168
CA $340 total
includes taxes & fees
Nov 9 - Nov 10
Bright 2-Bedroom Apartment Near Downtown Thomaston
A kitchen with a large island, two bar stools, wooden cabinets, a red refrigerator, and a view of the outdoors through large windows.

13. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
The price is CA $127
CA $313 total
includes taxes & fees
Nov 10 - Nov 11
Spacious 1 Bedroom Cottage Close to Everything 5
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, (41 reviews)
"Great Stay!"
United States
Pastor Heidi G.
The price is CA $182
CA $392 total
includes taxes & fees
Nov 9 - Nov 10
Peaceful, Centrally Located Home with Seasonal River Views
A living room with a sofa, a coffee table, a TV, a fireplace, and a window with curtains.

15. Fully Updated Airy Historic Home in West Rockport

Fully Updated Airy Historic Home in West Rockport
Rockport
The price is CA $200
CA $817 total
includes taxes & fees
Oct 26 - Oct 27
Fully Updated Airy Historic Home in West Rockport
A small cabin with a wooden deck, surrounded by trees in a wooded area.

16. Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.6 out of 10, Exceptional, (18 reviews)
"Great central location"
United States
Bruce O.
The price is CA $172
CA $368 total
includes taxes & fees
Oct 26 - Oct 27
Spacious 1 Bedroom Cottage Close to Everything 3
A cozy living room with a wooden ceiling, a white sofa, a coffee table, and a dark armchair.

17. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (71 reviews)
"Great place and great restaurants."
United States
Julie D.
The price is CA $218
CA $447 total
includes taxes & fees
Nov 2 - Nov 3
A Spacious Vacation Cottage in Sheepscot Harbour
A cozy interior of a geodesic dome tent with a bed, a sofa, a small table with a bottle, a fireplace, and a view of the outdoors.

18. Come Spring Farm Glamping Dome 2

Come Spring Farm Glamping Dome 2
Union
5.6 out of 10, (4 reviews)
"My friends and I had a great time at Come Spring Farm! We got hit with a lot of rain as soon as we arrived and it was really cool to watch the storm through the windows in the dome. We were impressed with the bathroom/shower facilities and the Coop hang out space, and I was thrilled to help feed the animals in the morning. We hope to return soon!"
United States
Healy C.
The price is CA $231
CA $335 total
includes taxes & fees
Oct 26 - Oct 27
Come Spring Farm Glamping Dome 2
A wooden cabin interior with a loft bedroom, a kitchen area, and a dining space.

19. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (5 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is CA $133
CA $315 total
includes taxes & fees
Oct 27 - Oct 28
Cheerful Cottage with Loft 9
Two Adirondack chairs facing a body of water with a bridge in the background.

20. Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River

Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River
Edgecomb
9.8 out of 10, Exceptional, (90 reviews)
"Lovely cottage with a great view."
United States
Ann M.
The price is CA $247
CA $483 total
includes taxes & fees
Oct 28 - Oct 29
Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River
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

Rockland Harbor Hotel

Rockland Harbor Hotel

10/10 Excellent
"Beautiful view of the harbor and gorgeous sunrise. Very large rooms, clean and friendly staff."
Brian 1-night trip
Posted 14 hours ago
Rockland Harbor Hotel

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Waldoboro vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Waldoboro vacation rentals we have selected for you start as low as CA $167 per night. Entering your travel dates in the search wizard 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. 

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?

Oceanview Bungalow Style Home in Owls Head: This vacation home rental outside Waldoboro is located by the ocean and has a balcony, a terrace, and air-conditioning to put you at ease 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. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Waldoboro?

With 22 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.