Waldoboro Holiday Rentals

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Holiday Rentals in Waldoboro

Trade Winds on the Bay

3.5 star property
8.4 out of 10, Very good, (280)
"The rooms were spacious and the view was beautiful!"
Trade Winds on the Bay

Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

2.0 star property
8.8 out of 10, Excellent, (11)
"The home is on a beautiful, private piece of land right on the St. George River estuary. The views are absolutely stunning and there is a short path right to the water and rocks. It was a perfect spot for two couples to relax and convenient to explore the midcoast region."
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

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

8.6 out of 10, Excellent, (8)
"We had the best nights' sleep of our lives in this rustic cabin! Super quiet and peaceful. Excellent star watching. Masha was so nice and extremely hospitable! "
The price is NZ$188
includes taxes & fees
13 Oct - 14 Oct
Charming Off- Grid cabin 5 min from the ocean in Midcoast Maine

Point Lookout

3.0 star property
9.6 out of 10, Exceptional, (9)
"Great location. Away from the down town bustle, but close enough to enjoy the best of both worlds. Clean cabin, great amenities. "
Point Lookout

Pine Grove Cottages

2.5 star property
9.8 out of 10, Exceptional, (89)
"Wonderful quiet place, The Host was a great person."
The price is NZ$452
includes taxes & fees
6 Oct - 7 Oct
Pine Grove Cottages

Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

8.8 out of 10, Excellent, (39)
"This was our second stay here. We love the comfort of this home and the location is perfect."
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

10.0 out of 10, Exceptional, (104)
"If you plan to visit Boothbay Harbor, you won't find a better place! The lakefront property is very close to town but offers a quiet location in a private neighborhood. Beautiful and bright interior in a natural setting. One of the best places I've stayed at. Great for kayaking and fishing too! "
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town

9.0 out of 10, Wonderful, (74)
"We had a great stay! The property was clean and exactly as described. Great location. The owners were very responsive ."
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town

Morning sun, coffee in hand, a good book and so much more...

9.8 out of 10, Exceptional, (84)
"It was so pleasant and relaxing. Close to the city and harbor "
Morning sun, coffee in hand, a good book and so much more...

Maine Coast House with Spectacular Ocean Views and Beach for Swimming

9.4 out of 10, Exceptional, (26)
"Perfect base for exploring the mid-coast region. "
The price is NZ$901
includes taxes & fees
3 Oct - 4 Oct
Maine Coast House with Spectacular Ocean Views and Beach for Swimming

Timeless Days: Maine Coast Waterfront, Fisherman's Cottage With Deepwater Dock

10.0 out of 10, Exceptional, (78)
"Very pleased with the house, the location, everything!"
Timeless Days: Maine Coast Waterfront, Fisherman's Cottage With Deepwater Dock

Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.

10.0 out of 10, Exceptional, (135)
"We loved this place! It was beautiful and in a convenient location. We highly recommend it."
Unobstructed Ocean Views Private Onsite Access to the water & small sandy beach.

Renovated home with water views, dock access, - dogs okay

6.6 out of 10, (8)
"location was great. bed sheets/ covers were not clean. nice kitchen no outside chairs or deck to enjoy the Maine weather."
Renovated home with water views, dock access, - dogs okay

Newly Renovated Cozy Cove Cabin at White Anchor Inn

8.0 out of 10, Very good, (5)
The price is NZ$280
includes taxes & fees
8 Oct - 9 Oct
Newly Renovated Cozy Cove Cabin at White Anchor Inn

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

7.0 out of 10, Good, (4)
"Affordable and quiet location that felt safe and is conveniently close to Boothbay Harbor & surrounding attractions. "
The price is NZ$243
includes taxes & fees
2 Oct - 3 Oct
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

9.6 out of 10, Exceptional, (79)
"Great stay, wonderful location"
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

Make Shimmering River Retreat your Maine Coastal getaway!

9.6 out of 10, Exceptional, (39)
"It was a very nice place for a family vacation. There was plenty of room for all of us (10).Yard and inside games provided along with kayaks for the river and a pool."
Make Shimmering River Retreat your Maine Coastal getaway!

Unique Coastal Maine Flower Farm Stay

9.6 out of 10, Exceptional, (15)
"The rental is a spacious 2-bedroom apartment overlooking the grounds, greenhouses, and fields of the unique Leafsong farm, out in the quiet and leafy countryside southwest of Belfast. You may meet the peacocks, sheep, mule, and horse who also call this place home. Many treasures to be found at the flower shop on the premises."
The price is NZ$722
includes taxes & fees
2 Oct - 3 Oct
Unique Coastal Maine Flower Farm Stay

WATERFRONT Retreat venue for up to 60 guests!… Weddings, Reunions, Meetings!……

WATERFRONT Retreat venue for up to 60 guests!… Weddings, Reunions, Meetings!……

Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland

9.6 out of 10, Exceptional, (90)
"We enjoyed our stay very much. The view was perfect and we really enjoyed sitting on the porch."
Quiet Ocean Front Cottage With Stunning Views & Private Beach Close To Rockland
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

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$188 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. 

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?

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage: This holiday home rental outside of Waldoboro offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

How many holiday rentals will I find in Waldoboro?

With 21 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.