Waldoboro holiday lettings

We found 524 holiday rentals — enter your dates for availability

Discover a selection of 22 homes and other holiday rentals in Waldoboro that are perfect for your trip. Holiday rentals offer the amenities that you expect for your family, friends or furry companion, such as a hot tub and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Waldoboro

Showing deals for:6 Mar - 13 Mar

Image gallery for The Lake House- canoes, kayaks, pool table, ping pong table, sleeps 16

Exterior
9.6 out of 10, Exceptional, (40 reviews)
Exceptional
(40 reviews)

The Lake House- canoes, kayaks, pool table, ping pong table, sleeps 16

Warren, ME

8% off
Price is £5,748
for 7 nights, 1 home
£821 per night
includes taxes & fees
The Lake House- canoes, kayaks, pool table, ping pong table, sleeps 16

Find spaces that suit your style

Why people love visiting relaxing Waldoboro

The area's art galleries and museums are just some of the reasons to come on holiday to Waldoboro. This city's gardens, local tours and bars attract many visitors, as does its relaxing and welcoming location. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Waldoboro

Are you searching for attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Waldoboro a one-of-a-kind holiday spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Samoset Resort Golf Course (14.5 mi / 23.3 km)
  • Owls Head State Park (16.3 mi / 26.2 km)
  • Maine State Prison Store (9.2 mi / 14.8 km)
  • Cellardoor Winery (19.2 mi / 30.9 km)
  • Boothbay Golf Course (19.7 mi / 31.6 km)
  • Morse's Sauerkraut (7.6 mi / 12.2 km)

Exploring the natural landscape of Waldoboro

Whether you're looking for adventure or just want to appreciate the scenery, Waldoboro is a great place to get out in nature. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • St. George River (6.8 mi / 11 km)
  • Damariscotta Lake (7.6 mi / 12.3 km)
  • Rockland Harbor Park (13.3 mi / 21.4 km)
  • Sandy Beach (13.4 mi / 21.6 km)
  • La Verna Preserve (14.3 mi / 23 km)
  • Rockport Marine Park (16.2 mi / 26.1 km)

Transport options to and around Waldoboro

Fly into Rockland, ME (RKD-Knox County Regional), the closest airport, located 14.1 mi (22.7 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Wiscasset, ME (ISS), which is 19 mi (30.6 km) away.

Frequently asked questions

What is the best area to stay in Waldoboro when booking a holiday rental?
When booking a holiday rental in Waldoboro, Maine, one of the best areas to consider is the charming downtown district. This area offers a delightful blend of quaint shops, local eateries, and a vibrant community atmosphere. Staying here puts you within walking distance of several attractions, including the Waldoboro Historical Society, where you can learn about the town's rich maritime history, and the picturesque Medomak River, superb for scenic strolls or enjoying a peaceful picnic.

Another appealing option is the area surrounding the Waldoboro Harbor. This stunning waterfront location is ideal for those who appreciate coastal views and the relaxing sound of the waves. The nearby Fishermen's Memorial Park is a lovely spot to unwind, and it often hosts local events that showcase the region's culture and community spirit. In this area, you'll find a variety of holiday rental properties, suiting different tastes and budgets, ensuring a comfortable stay for all visitors.
How much does it cost to rent a holiday home in Waldoboro?
Prices for holiday rentals in Waldoboro vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Waldoboro to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Waldoboro holiday house rentals?
You can find great discounts on house rentals in Waldoboro on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Waldoboro?
For renting a beach house in Waldoboro, Maine, the area along the Medomak River and the scenic coastline offers appealing options. Properties near the river often provide lovely waterfront views and opportunities for kayaking or fishing, with many houses featuring amenities such as private docks, outdoor fire pits, and spacious decks for enjoying the tranquil surroundings.

In addition, the stretch of coastline near Moody's Beach is particularly popular, where you'll find charming cottages and homes that typically include features like fully equipped kitchens, barbecue grills, and easy beach access. Many rentals in this area are family-friendly, providing ample space for children to play and explore.
What is the most popular type of holiday rental accomodation in Waldoboro?
In Waldoboro, holiday houses are the most popular choice, with around 18 available in various scenic locations. These properties often come with multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Additionally, several cottages and cabins can be found, offering a more rustic charm and a closer connection to nature. Many of these rentals include outdoor spaces, such as decks or patios, where guests can relax and enjoy the tranquil surroundings.
Are there any family house rentals in Waldoboro?
In Waldoboro, Maine, there are numerous family-friendly houses available—about 22 in total. This charming coastal town offers a picturesque setting with access to beautiful beaches and scenic views along the Medomak River. Many of these properties provide spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for children to enjoy.
Can I find long-stay holiday rentals in Waldoboro?
A long-stay holiday rental in Waldoboro is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Waldoboro?
In Waldoboro, there are several pet-friendly house rentals available, offering a welcoming environment for travellers with furry companions. Many of these properties are equipped with essential amenities such as full kitchens, comfortable living spaces, and outdoor areas where pets can play.

The town is situated along the beautiful coastline of Maine, providing easy access to picturesque beaches and scenic waterfronts. Nearby, the Medomak River offers opportunities for kayaking and fishing, making it a great spot for outdoor activities with your pet.
Are there any remote work holiday rentals in Waldoboro?
In Waldoboro, there are numerous remote work holiday rentals available, with around 31 options to choose from. These properties cater to those looking to blend work and leisure in a tranquil coastal setting. Most rentals are equipped with essential amenities such as Wi-Fi, dedicated office spaces, and comfortable desks, providing an ideal environment for productivity. Many also feature additional conveniences like laptop workspaces and ergonomic chairs, ensuring a comfortable workspace during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Waldoboro holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Waldoboro with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Waldoboro?
In Waldoboro, popular holiday rental amenities typically include well-equipped kitchens, ensuring guests can prepare their own meals during their stay. Most rentals come with essential appliances such as microwaves, refrigerators, and stovetops, along with cookware, dishware, and utensils for convenience.
When is the best time to visit Waldoboro for a holiday rental?
The best time to visit Waldoboro for a holiday rental is during the peak season from June to August, particularly in July when the area is at its most vibrant. This period attracts visitors keen to enjoy the stunning coastal views, fresh seafood, and an array of outdoor activities. The warm summer weather, with average temperatures in the high teens to low twenties Celsius, is superb for exploring the picturesque beaches and indulging in water sports like kayaking and paddleboarding.

July is particularly lively, with local events and markets showcasing Maine's rich culture and community spirit. It's an ideal time for travellers, as you can partake in everything from hiking the scenic trails to visiting charming local shops and art galleries.

For those looking to travel on a budget, consider planning your trip in December. While this may be considered low season, it offers a unique charm with opportunities for winter activities and a quieter atmosphere to enjoy the quaint town.
How early should I book a Waldoboro holiday rental?
Book your Waldoboro holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Waldoboro?
In Waldoboro, Maine, visitors can explore a variety of attractions that reflect the town's coastal charm and history. The Waldoboro Historical Society offers insights into the local heritage, showcasing exhibits and artifacts from the area's past. Nearby, the scenic Medomak River provides opportunities for kayaking and fishing, making it a popular spot for outdoor enthusiasts.

The town is also known for its vibrant arts scene, with local galleries displaying works from regional artists. For those interested in history, the iconic Old Jail Museum is a fascinating visit, highlighting the town's early law enforcement history.
Can I change or cancel my Waldoboro home rental booking on Vrbo?
To find Waldoboro holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Waldoboro holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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