Waldoboro holiday rentals

We found 579 holiday rentals — enter your dates for availability
Discover a selection of 21 homes, 11 apartments 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 Nov - 13 Nov

Property grounds
Outdoor dining
Living area
More ocean views from the lower level family room
Exceptional
(29 reviews)

Oceanfront, views from every room! Spacious midcoast retreat with private dock

Round Pond

8% off
AU$6,426
for 7 nights, 1 home
AU$918 per night
includes taxes & fees
Oceanfront, views from every room! Spacious midcoast retreat with private dock
Galley Kitchen with dining counter.
Living Room (Full Sleep Sofa), Open Kitchen, Adjacent Dining Room
Fall Colors at Sea Lavender
Fire pit (wood provided) along the shore
Exceptional
(72 reviews)

Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front

Newcastle

6% off
AU$4,747
for 7 nights, 1 cottage
AU$678 per night
includes taxes & fees
Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front
Living area
Kitchen seating area
Interior
upstairs TV room
Exceptional
(21 reviews)

Handcrafted Post and Beam Saltbox

Bremen

8% off
AU$2,413
for 7 nights, 1 home
AU$345 per night
includes taxes & fees
Handcrafted Post and Beam Saltbox
Living Room with gas fireplace
Property grounds
Fitness facility
Property grounds
Exceptional
(27 reviews)

Maine Coast House with Spectacular Ocean Views and Beach for Swimming

South Bristol

8% off
AU$5,630
for 7 nights, 1 home
AU$804 per night
includes taxes & fees
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Living area
Property grounds
Exterior
Property grounds
Exceptional
(11 reviews)

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

Spruce Head

8% off
AU$3,665
for 7 nights, 1 home
AU$524 per night
includes taxes & fees
Coastal Spruce Head Retreat dog friendly & near restaurants, stores, activities.
Main living area
Welcome to the Perch!
Exterior
Stairs to the main living area - 18 steps, wide and study, with handrail.
Exceptional
(20 reviews)

The Perch - A cozy cottage minutes from Tenants Harbor, with water access!

Tenants Harbor

12% off
AU$1,630
for 7 nights, 1 home
AU$233 per night
includes taxes & fees
The Perch - A cozy cottage minutes from Tenants Harbor, with water access!
Kitchen and Dining view from the Living Room
Front of the house (Fall)
1st Floor Main Queen Bedroom
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$2,344
for 7 nights, 1 home
AU$335 per night
includes taxes & fees
Weskeag Cottage - Arcade, Fire Pit, Clean, Bright, Nearby Coastal Activities
Living area
Living area
Interior
Side of the house with the screened in porch.
Exceptional
(33 reviews)

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

Round Pond

8% off
AU$3,033
for 7 nights, 1 home
AU$433 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--
Charming on your arrival...
Relax with friends around the fireplace in the Livingroom.
Exceptional
(92 reviews)

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

New Harbor

7% off
AU$2,024
for 7 nights, 1 home
AU$289 per night
includes taxes & fees
Slow Down & Go Back in Time-Relax Completely in Our Maine Home
Lower level entry and open closet
Kitchen on main level
Back deck off living room
Front door entry
Exceptional
(12 reviews)

Charming 3-bedroom house with AC and WiFi in Thomaston

Thomaston

8% off
AU$3,097
for 7 nights, 1 home
AU$442 per night
includes taxes & fees
Charming 3-bedroom house with AC and WiFi in Thomaston
Living area
Exterior detail
Private kitchen
Interior
Exceptional
(24 reviews)

Foundry Guest Apartment

Rockport

9% off
AU$2,415
for 7 nights, 1 apartment
AU$345 per night
includes taxes & fees
Foundry Guest Apartment

  • 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:

  • 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)
  • Pemaquid Craft Co-op (16.4 mi / 26.4 km)
  • Cellardoor Winery (19.2 mi / 30.9 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)
  • Rockport Marine Park (16.2 mi / 26.1 km)
  • Pemaquid Beach Park (17.1 mi / 27.5 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 most popular type of holiday home accommodation in Waldoboro?
The most popular types of holiday homes in Waldoboro are houses. Want something different? Stayz has a variety of options to match the diverse needs of our guests, so you'll see holiday properties in all shapes and sizes, and for all budgets. The ideal fit is waiting for you — get yours today.
How much does it cost to rent a holiday home in Waldoboro?
Several factors affect what you'll pay for your holiday home in Waldoboro, such as the type of property, season and length of stay. However, all Stayz homes have something in common — unbeatable value. Simply add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Waldoboro?
Prices for beach houses in Waldoboro may vary depending on the style and size of the property and time of year you're travelling. All you have to do is enter your travel dates into Stayz and the number of guests to view your home options and prices. From there you can use our filters to narrow down your search by nearby activities, amenities, ratings and more.
Are there pet-friendly holiday homes in Waldoboro?
Pack a suitcase for your puppy dog because Waldoboro has 34 stays that welcome pets with open arms. Let your furriest pal enjoy the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your dates and destination, then check the "Pets allowed" filter box.
What are popular home amenities in Waldoboro?
When it comes to home amenities that guests prefer in Waldoboro, a garden, an electric car charging station and a nearby river are at the top of the list. With Stayz holiday homes, there are options to suit your style and taste, whether you're going away with your partner, your family or even pets.
Are there large group holiday homes in Waldoboro?
You'll find 19 properties in Waldoboro that can sleep five or more guests. From family reunions to events like birthday parties, these stays have enough room to chill out with your favourite people.
Are there holiday homes in Waldoboro that welcome kids?
With 34 family-friendly holiday homes available in Waldoboro, now is a superb time to introduce the little ones to the pleasures of travel. Simply click on our "Properties good for families" filter box to browse stays that come with amenities ideal for holidaying families, like living rooms, outdoor spaces, entertainment units and bunk beds.
What are the top attractions for families in Waldoboro?
Keep the kids occupied at these popular family-friendly attractions in Waldoboro:
  • Penobscot Marine Museum
  • Damariscotta Lake
  • Damariscotta Lake State Park
Are there one-bedroom holiday homes in Waldoboro?
You can choose from six one-bedroom homes in Waldoboro. Whether you want a comfy cottage or a cabin, Stayz's one-bedroom homes are ideal if you don't require tons of space. One of the perks of having your own place? You won't have to share your holiday with strangers.
Can I find two-bedroom holiday homes in Waldoboro?
Take your pick of 10 two-bedroom homes in Waldoboro. Give your little ones the second room or maybe fill it with a couple of your best friends. There's plenty of space for whoever's lucky enough to be joining your journey.
Are there holiday homes with WiFi in Waldoboro?
Whether you'd like to keep up with the news, look over emails or surf your social networks, there are 11 holiday homes with WiFi in Waldoboro. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.
How can I find holiday homes with air conditioning in Waldoboro?
Pick from 15 Stayz holiday homes with air conditioning in Waldoboro providing that cooling breeze and extra element of comfort. Enter your desired travel dates and then make use of our filters to help you find stays with air conditioning.
How old do you have to be to rent a holiday home in Waldoboro?
The minimum required age is usually 16, 18 or 21. It can differ between properties on Stayz, so look at the rules of your preferred Waldoboro holiday home before booking your escape.
How long can I rent a holiday home in Waldoboro for?
The length of time you can rent a holiday home in Waldoboro is down to the property. Just enter your preferred dates to view a list of options offering extended stays. With loads of features like full kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to find the perfect place to call your home away from home in Waldoboro.

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