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

Waldoboro Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Waldoboro holiday 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 NZ$325
includes taxes & fees
2 Oct - 3 Oct
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 NZ$1,906
includes taxes & fees
4 Oct - 5 Oct
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, (502 reviews)
"Its a place to stay."
United States
Todd
The price is NZ$158
includes taxes & fees
26 Oct - 27 Oct
Trade Winds on the Bay
A living room with a fireplace, a mounted TV, and bookshelves filled with books.

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

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
9.8 out of 10, Exceptional, (49 reviews)
"We loved our cozy stay everything was clean and tidy, and we had everything that we needed"
United States
Betty Jo O.
The price is NZ$709
includes taxes & fees
4 Oct - 5 Oct
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
A spacious tent with a large skylight, a bed, a sofa, a lamp, and a fireplace.

5. 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 NZ$498
includes taxes & fees
3 Oct - 4 Oct
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
A grassy yard with a small table and chairs, a house, and a lake in the background.

6. 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
The price is NZ$681
includes taxes & fees
6 Oct - 7 Oct
Rustic Retreat Across From Lake; Family Friendly!
A bedroom with a bed, a bedside table, and a window with curtains.

7. Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
9.0 out of 10, Wonderful, (11 reviews)
"Great location, excellent accommodations, perfect for our weekend adventure."
United States
Brian
The price is NZ$319
includes taxes & fees
17 Oct - 18 Oct
Peaceful Intown Studio ~ Walk to Shops & Dining
A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

8. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (55 reviews)
"Perfect location to everything. Spacious house and clean. The directions for check in and check out where very clear and helpful!"
United States
Brianna M.
The price is NZ$459
includes taxes & fees
1 Nov - 2 Nov
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.

9. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (40 reviews)
"Great Stay!"
United States
Pastor Heidi G.
The price is NZ$526
includes taxes & fees
1 Nov - 2 Nov
Peaceful, Centrally Located Home with Seasonal River Views
A wooden deck with Adirondack chairs and a grill.

10. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.2 out of 10, Wonderful, (14 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 NZ$447
includes taxes & fees
26 Oct - 27 Oct
Bright 2-Bedroom Apartment Near Downtown Thomaston
A modern living room with a large window, a wooden ceiling, and a view of a green landscape.

11. 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.
The price is NZ$443
includes taxes & fees
18 Oct - 19 Oct
Come Spring Farm Airstream , Lake & farm animals
A modern kitchen with a central island, built-in appliances, and a dining area with a high chair.

12. 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, (44 reviews)
"Wonderful place at a great price!"
United States
Stephen H.
The price is NZ$747
includes taxes & fees
1 Nov - 2 Nov
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

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

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (35 reviews)
"Very nice tiny house in a quiet neighborhood. Easy walk to downtown"
United States
sarah
The price is NZ$269
includes taxes & fees
8 Oct - 9 Oct
Simplicity-Just what you need! STR24-20
A room with a large window offering a view of a snowy landscape and a body of water.

14. Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (101 reviews)
"Great location close to town"
United States
Rich W.
The price is NZ$681
includes taxes & fees
26 Oct - 27 Oct
Comfortable, Close to Town Home, with Oceanview.
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.

15. 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 NZ$438
includes taxes & fees
18 Oct - 19 Oct
Come Spring Farm Glamping Dome 2
A wooden deck with two blue Adirondack chairs, surrounded by white flowers and trees.

16. Luxury Yurt at Seaside Farm in Friendship

Luxury Yurt at Seaside Farm in Friendship
Friendship
The price is NZ$1,191
includes taxes & fees
4 Oct - 5 Oct
Luxury Yurt at Seaside Farm in Friendship
A wooden deck with a glass door leading to a room.

17. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
8.8 out of 10, Excellent, (5 reviews)
"Great location awesome place to take it easy for a few"
United States
Gene
The price is NZ$376
includes taxes & fees
5 Oct - 6 Oct
Tiny Cottage Near Everything 10
Two Adirondack chairs facing a body of water with a bridge in the background.

18. 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, (89 reviews)
"Lovely cottage with a great view."
United States
Ann M.
The price is NZ$534
includes taxes & fees
27 Oct - 28 Oct
Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River
A kitchen with wooden ceiling, a bar area with two chairs, a red appliance, and a view of the outdoors.

19. Spacious 1 Bedroom Close to Everything 4

Spacious 1 Bedroom Close to Everything 4
Edgecomb
9.8 out of 10, Exceptional, (25 reviews)
"This was a lovely little cabin. Everything was as described and my husband and I really enjoyed our stay."
Canada
Christine M.
The price is NZ$459
includes taxes & fees
27 Oct - 28 Oct
Spacious 1 Bedroom Close to Everything 4
A cozy living room with a wooden ceiling, a white sofa, a coffee table, and a dark armchair.

20. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (70 reviews)
"Great place and great restaurants."
United States
Julie D.
The price is NZ$540
includes taxes & fees
25 Oct - 26 Oct
A Spacious Vacation Cottage in Sheepscot Harbour
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

Glen Cove Inn & Suites

Glen Cove Inn & Suites

10/10 Excellent
"Staff was fantastic, very helpful."
Julian 1-night trip
Posted less than an hour ago
Glen Cove Inn & Suites

Find out more about Waldoboro

Everything you need to know about Waldoboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Waldoboro holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Waldoboro holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Waldoboro holiday rentals we have selected for you start as low as NZ$158 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 holiday 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 holiday.

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 holiday rentals in Waldoboro?

Yes, there are holiday rentals in Waldoboro close to Morse's Sauerkraut, or you can select a more 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 holiday rentals that Waldoboro has to offer?

Oceanview Bungalow Style Home in Owls Head: This holiday 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Waldoboro?

With 22 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Fawcett's Antique Toy and Art Museum and St. George River.

What’s a holiday rental in Waldoboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Waldoboro. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family getaway.