Waldoboro holiday rentals

We found 553 holiday rentals — enter your dates for availability
Discover a selection of 21 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:18 Dec - 25 Dec

Pick your chair. While watching the Friendship Lobster Boast Races.
Sea view through wavy glass in living room.
Matching Dinning Hutch.
Your " Private" wharf from water.
Exceptional
(99 reviews)

Historic "Wilbur Morse" Friendship Maine Ocean Home

Friendship

17% off
AU$8,108
for 7 nights, 1 home
AU$1,158 per night
includes taxes & fees
Historic "Wilbur Morse" Friendship Maine Ocean Home
Interior
Living Area with soaring Cathedral Ceiling
View the pond from the peaceful covered porch.
King bed with light cotton quilt in summer & down bedding for the cooler months.
Exceptional
(61 reviews)

20% Off Sept. Bookings, 3 night min., 1st flr King & Full Loft, Pets Free

Round Pond

8% off
AU$2,840
for 7 nights, 1 cottage
AU$406 per night
includes taxes & fees
20% Off Sept. Bookings, 3 night min., 1st flr King & Full Loft, Pets Free
Hefty ships ladder to loft. 4 Skylights.
Pemaquid Beach 10 minutes
Exterior detail
Exterior
Exceptional
(64 reviews)

Our Premier Cottage - Laundry, Large, Luxurious King Bedroom, Pets Free

Round Pond

9% off
AU$2,994
for 7 nights, 1 cottage
AU$428 per night
includes taxes & fees
Our Premier Cottage - Laundry, Large, Luxurious King Bedroom, Pets Free
Interior
Property grounds
Exterior
Living area
Exceptional
(14 reviews)

Coastal Spruce Head Retreat dog friendly & near restaurants, stores, activities.

Spruce Head

8% off
AU$4,039
for 7 nights, 1 home
AU$577 per night
includes taxes & fees
Coastal Spruce Head Retreat dog friendly & near restaurants, stores, activities.
1st Floor Main Queen Bedroom
Front of the house (Fall)
Front of the house.
Main Living Room with 55" Smart TV, Couch, Two Armchairs.
Exceptional
(24 reviews)

Weskeag Cottage - Arcade, Fire Pit, Clean, Bright, Nearby Coastal Activities

South Thomaston

15% off
AU$2,987
for 7 nights, 1 home
AU$427 per night
includes taxes & fees
Weskeag Cottage - Arcade, Fire Pit, Clean, Bright, Nearby Coastal Activities
Living area
Living area
Interior
Living area
Exceptional
(35 reviews)

The Round Pond Getaway. Screened Porch · Fire Pit · Walk to Harbor

Round Pond

8% off
AU$2,991
for 7 nights, 1 home
AU$427 per night
includes taxes & fees
The Round Pond Getaway. Screened Porch · Fire Pit · Walk to Harbor
Settle & relax on the deck, flagstone patio, or 'round the fire pit--
Sea-air nourishes our flowerbox blossoms all summer--
Relax with friends around the fireplace in the Livingroom.
Charming on your arrival...
Exceptional
(96 reviews)

Slow Down & Go Back in Time-Relax Completely in Our Maine Home

New Harbor

7% off
AU$1,991
for 7 nights, 1 home
AU$284 per night
includes taxes & fees
Slow Down & Go Back in Time-Relax Completely in Our Maine Home
Interior
Kitchen on main level
Back deck off living room
Lower level entry and open closet
Exceptional
(14 reviews)

Charming 3-bedroom house with AC and WiFi in Thomaston

Thomaston

8% off
AU$3,471
for 7 nights, 1 home
AU$496 per night
includes taxes & fees
Charming 3-bedroom house with AC and WiFi in Thomaston

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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:

  • Maine State Prison Store (9.2 mi / 14.8 km)
  • Samoset Resort Golf Course (14.5 mi / 23.3 km)
  • Owls Head State Park (16.3 mi / 26.2 km)
  • Cellardoor Winery (19.2 mi / 30.9 km)
  • Savage Oakes Vineyard and Winery (10.2 mi / 16.4 km)
  • Boothbay Golf Course (19.7 mi / 31.6 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 considering a holiday rental in Waldoboro, Maine, the area around the charming downtown is an excellent choice. This neighbourhood offers a lovely blend of local shops, cafés, and eateries, providing visitors with a taste of the region's hospitality. A popular attraction nearby is the stunning Waldoboro Harbor, where you can enjoy picturesque views and perhaps indulge in some fresh seafood.Another point of interest is the historical village of Waldoboro, which showcases the town's rich heritage, including the fascinating Waldoboro Historical Society Museum. This area typically features a variety of holiday rentals, ranging from cosy cottages to more spacious homes, suiting different preferences and group sizes.
Where are the best areas for renting a beach house in Waldoboro?
For renting a beach house in Waldoboro, the picturesque coastline along the Medomak River is an excellent choice. This area offers a variety of charming holiday rentals that provide easy access to both the river and the nearby Atlantic Ocean. Many properties here come with desirable amenities such as private decks, outdoor seating areas, and fully equipped kitchens, making them superb for families or groups looking to enjoy a relaxing seaside getaway.The neighbourhood around Waldoboro's historic downtown is also appealing, where visitors can find quaint cottages and larger homes that often feature lovely gardens and views of the water. These rentals typically include comfortable living spaces, ample parking, and sometimes even access to kayaks or bicycles for exploring the local waterways.Nearby attractions such as the scenic Moody's Diner and local artisan shops add to the charm of the area, providing convenient dining and shopping options. Additionally, the proximity to the beautiful Pemaquid Point Lighthouse and beach offers opportunities for picturesque day trips, with many rentals being ideally situated for easy access to these iconic coastal spots.
What is the most popular type of holiday rental accomodation in Waldoboro?
In Waldoboro, holiday houses are the most popular type of holiday rental, with around 76 available throughout the area. These homes often provide spacious layouts that include multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation, making them superb for families or larger groups. Additionally, there are about 24 apartments and approximately 20 cottages, suiting those who may prefer a more compact living arrangement. For a more rustic experience, several cabins can also be found, offering a unique charm amidst the natural beauty of the region.
Are there any family house rentals in Waldoboro?
In Waldoboro, Maine, there are around 26 family-friendly house rentals available. This charming coastal town offers a variety of options suitable for families, featuring spacious living areas, fully equipped kitchens, and outdoor spaces great for children to play. Many properties may also include amenities such as Wi-Fi and laundry facilities, ensuring a comfortable stay for guests.Visitors to Waldoboro can enjoy local attractions like the scenic Medomak River and the nearby Damariscotta Lake, which is ideal for swimming and fishing. The area is steeped in history, with opportunities to explore local shops and eateries that serve up delicious seafood.
Are there pet-friendly house rentals in Waldoboro?
In Waldoboro, there are several pet-friendly house rentals available, with a total of sixteen options for travellers seeking a comfortable stay with their furry companions. Many of these properties typically feature spacious yards, allowing pets to roam freely, as well as amenities such as fully equipped kitchens, cosy living areas, and outdoor spaces like decks or patios where guests can enjoy the serene surroundings.The neighbourhood itself offers a charming mix of coastal and rural experiences, with easy access to local attractions and outdoor activities. Nearby, Medomak River is great for leisurely walks, and there are various parks and nature trails in the area where pets are welcome, providing great opportunities for exploration and play.
Are there any remote work holiday rentals in Waldoboro?
In Waldoboro, Maine, there are numerous remote work holiday rentals available, with about 124 options to choose from. This charming town on the Midcoast offers a serene environment great for those looking to balance work and leisure. Many of these properties come equipped with essential amenities such as reliable Wi-Fi and dedicated workspace areas, ensuring a productive stay.The town's picturesque scenery, including the beautiful Medomak River and nearby coastal attractions, provides an ideal backdrop for breaks during the workday. Additionally, visitors can explore local cafes and shops that contribute to the vibrant community atmosphere. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Waldoboro?
In Waldoboro, popular holiday rental amenities include kitchens, which are essential for travellers looking to prepare their own meals. Many properties also feature decks or patios, allowing guests to enjoy the picturesque surroundings while relaxing outdoors. Additionally, rentals often come equipped with blenders for making smoothies or other beverages, as well as coffee and tea makers for those who appreciate a morning brew. Onsite parking is another convenience, making it easy for visitors to explore the charming coastal area without any hassle.
When is the best time to visit Waldoboro for a holiday rental?
July is the most popular month to visit Waldoboro, offering a vibrant summer experience that draws families and beach enthusiasts alike. The peak season runs from June to August, when the coastal town buzzes with activity. During this time, visitors can enjoy the picturesque beaches, explore local seafood restaurants, and partake in various outdoor activities, all under the warm sun and pleasant temperatures averaging around 20 to 30 degrees Celsius.For those seeking a more tranquil experience, consider visiting in December. This month allows you to embrace the charm of Waldoboro during the quieter winter season, where you can enjoy cozy indoor activities and the beauty of the landscape dusted with snow. The atmosphere is peaceful, providing a superb backdrop for reflection and relaxation.
What are the top attractions in Waldoboro?
In Waldoboro, Maine, visitors can enjoy a range of local attractions that showcase the town's coastal charm and historical significance. The Waldoboro Historical Society offers insights into the area's rich history, including its shipbuilding heritage. Nearby, the Medomak River provides opportunities for kayaking and fishing, making it a popular spot for outdoor enthusiasts.The charming downtown area features quaint shops and local eateries, where visitors can sample fresh seafood and other regional delicacies. Additionally, the nearby beaches, such as Moody's Beach, offer a serene environment for relaxation and enjoying the picturesque coastline.
Are all fees included in the Waldoboro holiday homes prices shown on Stayz?
Stayz 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.
Are there any Waldoboro holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Waldoboro holiday homes?
You can find great discounts on holiday homes in Waldoboro on Stayz, 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.
Can I change or cancel my Waldoboro holiday home booking on Stayz?
To find Waldoboro holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Waldoboro?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Waldoboro holiday home?
Book your Waldoboro holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Waldoboro?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Waldoboro to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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