Waldoboro Holiday Rentals

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Our top choices for Waldoboro holiday rentals

The Entire Waldoboro Inn

The Entire Waldoboro Inn
Waldoboro
The price is AU$1,976
includes taxes & fees
11 Jan - 12 Jan 2026
The Entire Waldoboro Inn

Glamping at Maine Water Buffalo Farm

Glamping at Maine Water Buffalo Farm
1.0 star property
Appleton
10.0 out of 10, Exceptional, (2)
"Really great place….very thoughtful set up for us to enjoy."
United States
Peter P.
The price is AU$263
includes taxes & fees
31 Dec - 1 Jan 2026
Glamping at Maine Water Buffalo Farm

Tiny A-Frame Romantic Getaway

Tiny A-Frame Romantic Getaway
Wiscasset
10.0 out of 10, Exceptional, (3)
"Very nice and very quiet "
United States
justin s.
The price is AU$490
includes taxes & fees
15 Dec - 16 Dec
Tiny A-Frame Romantic Getaway

Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.4 out of 10, Very good, (323)
"Very nice place to stay. Staff helpful and friendly."
Canada
Dan
Trade Winds on the Bay

No bookings after 8/15/2024. Property sold. VRBO Thank you.

No bookings after 8/15/2024. Property sold. VRBO Thank you.
Searsmont
10.0 out of 10, Exceptional, (5)
"Love the cottage and very clean and quiet."
United States
Jeanne
The price is AU$214
includes taxes & fees
16 Dec - 17 Dec
No bookings after 8/15/2024. Property sold. VRBO Thank you.

Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
10.0 out of 10, Exceptional, (1)
"We had a wonderful weeklong stay while visiting family and friends in the area. We had everything we needed, and even started saying "we're going home" when leaving family.We never waited longer than 10 minutes for a reply from Jason. Everything was new, efficient, clean, and comfortable. Situated close to route 1 was especially convenient. The bedrooms on the back of the unit were cozy and quiet for sleeping. Morning coffee on the deck in the chairs was a delight.We will definitely stay again,...
United States
Lauren A.
The price is AU$319
includes taxes & fees
14 Dec - 15 Dec
Bright 2-Bedroom Apartment Near Downtown Thomaston

Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.

Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.
Boothbay
10.0 out of 10, Exceptional, (1)
"This efficiency apartment was nicely furnished with everything needed and conveniently located on the main road into Boothbay Harbor. The host was generous and accommodating. The region is fun to visit!"
United States
Mary D.
The price is AU$424
includes taxes & fees
14 Dec - 15 Dec
Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.

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

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
7.8 out of 10, Good, (7)
"Affordable and quiet location that felt safe and is conveniently close to Boothbay Harbor & surrounding attractions. "
United States
Melanie L.
The price is AU$304
includes taxes & fees
14 Dec - 15 Dec
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
9.8 out of 10, Exceptional, (43)
"House was very clean and beautiful the beach and fishing are were lovely as well very nicecstay"
United States
Lori R.
The price is AU$444
includes taxes & fees
14 Dec - 15 Dec
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.4 out of 10, Exceptional, (29)
"Amazing little house tucked away close to the river. It was very clean and nicely furnished. I had a great time staying here and it was very close to downtown Thomaston."
United States
Avery W.
The price is AU$417
includes taxes & fees
14 Dec - 15 Dec
Peaceful, Centrally Located Home with Seasonal River Views

Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Whitefield
9.8 out of 10, Exceptional, (30)
"We stayed in this cabin for two nights with our dog and it was very peaceful and fun! The cabin has a campfire, lots of batteries for charging, lights, battery fans, etc. There were many long walking trails with fun activities; like kayaking, axe throwing, a pizza oven… Exactly what we were looking for! Would stay again! "
United States
Ben R.
The price is AU$341
includes taxes & fees
14 Dec - 15 Dec
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (45)
"We loved our stay here! Check-in was easy and the host was responsive!"
United States
Jessica H.
The price is AU$377
includes taxes & fees
14 Dec - 15 Dec
2 Bedroom Close to Town Home

Romantic Coastal Escape near Harbor

Romantic Coastal Escape near Harbor
2.0 star property
Rockport
The price is AU$292
includes taxes & fees
14 Dec - 15 Dec
Romantic Coastal Escape near Harbor

Solitude @ The Offshore House

Solitude @ The Offshore House
Boothbay
9.8 out of 10, Exceptional, (7)
"Managers were very responsive and helpful. Condo was very clean and comfortable and close to the town of Boothbay Harbor and Ocean Point and the Botanic Gardens. "
United States
Linda O.
The price is AU$457
includes taxes & fees
16 Dec - 17 Dec
Solitude @ The Offshore House

Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach

Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach
Lincolnville
9.4 out of 10, Exceptional, (9)
"Such a beautiful property with an amazing view! "
United States
Katie F.
The price is AU$335
includes taxes & fees
14 Dec - 15 Dec
Ferry Cottage | Eco-Chic Escape, Ocean Views, Steps to Beach

Shipwright @ The Offshore House

Shipwright @ The Offshore House
Boothbay
9.4 out of 10, Exceptional, (13)
"Great location. Easy location to town and Dunkin Donuts accros street. "
United States
Steven
The price is AU$457
includes taxes & fees
14 Dec - 15 Dec
Shipwright @ The Offshore House

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
2.0 star property
Boothbay
6.0 out of 10, (5)
"It had a very homey feel, was nice to stay at for the night and wasn’t far from town."
United States
Audreyana P.
The price is AU$313
includes taxes & fees
2 Jan - 3 Jan 2026
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

Comfortable, Close to Town Home, with Oceanview.

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (84)
"Convenient location; host responsive; good towel supply. "
United States
Connie K.
The price is AU$506
includes taxes & fees
14 Dec - 15 Dec
Comfortable, Close to Town Home, with Oceanview.

Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
2.0 star property
Newcastle
The price is AU$253
includes taxes & fees
14 Dec - 15 Dec
Peaceful Intown Studio ~ Walk to Shops & Dining

Laughton House @ Pemaquid Beach

Laughton House @ Pemaquid Beach
Pemaquid Beach
10.0 out of 10, Exceptional, (8)
"This house is in a great location. We could walk to the beach, or to Fort Henry to let my grandsons run around. The house is lovely and had everything we needed. We have come to this area of Maine since 2017, and this had been our favorite place to stay! "
United States
Dawn W.
The price is AU$880
includes taxes & fees
21 Dec - 22 Dec
Laughton House @ Pemaquid Beach
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

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 favourite 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 depend 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 AU$304 per night. Entering your travel dates in the search wizard might find you 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. 

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?

Ocean-view penthouse with deck, gas grill, washer/dryer, full kitchen, & WiFi: This holiday home rental outside of Waldoboro is located next to a golf course, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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?

Cultural attractions include Fawcett's Antique Toy and Art Museum, whereas Morse's Sauerkraut is just one of the family-friendly sights. In the wider area, you’ll find St. George River and Damariscotta Lake.

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.