Family-Friendly Vacation Rentals in Paddleworks, ME: Compare 10+ Sites & Save

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  5.  Orrs Island
  6.  Paddleworks

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61 Best Family Vacation Rentals in Paddleworks (Starting from $196)

Betty's Place - Cozy ocean front getaway with views of Casco Bay
Betty's Place - Cozy ocean front getaway with views of Casco Bay
House
Orrs Island, ME, USA
0.7k from Paddleworks center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom4 Guests
New to Booking
$196
Average price / night
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Lowell's Cove Cottage - Quaint 2BR Cottage short walk away from Lowell's Cove
Lowell's Cove Cottage - Quaint 2BR Cottage short walk away from Lowell's Cove
Cottage
Orrs Island, ME, 04066, United States
0.5k from Paddleworks center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
9.6

Exceptional

23 reviews

$263
Average price / night
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Charming Retreat with Deck about 4 Mi From Casco Bay!
Charming Retreat with Deck about 4 Mi From Casco Bay!
House
Orrs Island, ME, USA
1.2k from Paddleworks center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms6 Guests
New to Booking
$405
Average price / night
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Spectacular Oceanfront House on Maine Coast
Spectacular Oceanfront House on Maine Coast
House
Orrs Island, ME, 04066, United States
0.8k from Paddleworks center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

6 Bedrooms10 Guests
10.0

Exceptional

22 reviews

$1090
Average price / night
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Clark Cove
Clark Cove
House
ME, USA
3.2k from Paddleworks center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

2 Bedrooms7 Guests
New to Booking
$648
Average price / night
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 Island Home Minutes Away from beaches, hiking, kayaking, or seaside dining
Island Home Minutes Away from beaches, hiking, kayaking, or seaside dining
House
Orr's Island', ME, 04066, United States
0.8k from Paddleworks center

Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms7 Guests
9.4

Superb

12 reviews

$427
Average price / night
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Harpswell Beach House
Harpswell Beach House
House
West Harpswell, ME, USA
3.7k from Paddleworks center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$635
Average price / night
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Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay
Panoramic Oceanfront Views Of Garrison Cove, Wills Gut And Casco Bay
House
Harpswell, ME, 04103, United States
1.7k from Paddleworks center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms10 Guests
9.8

Exceptional

158 reviews

$942
Average price / night
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Oceanfront Studio with Private Dock in Harpswell!
Oceanfront Studio with Private Dock in Harpswell!
Apartment
Dyer Cove, ME, USA
5.3k from Paddleworks center

Apartments, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$328
Average price / night
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Amazing Views, and Comfortable Spaces in this Well Appointed Island Home
Amazing Views, and Comfortable Spaces in this Well Appointed Island Home
House
Bailey Island, ME, 04003, United States
1.7k from Paddleworks center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater

6 Bedrooms14 Guests
9.8

Exceptional

81 reviews

$782
Average price / night
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Tide's Edge
Tide's Edge
House
Cundys Harbor, ME, USA
6.3k from Paddleworks center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay

4 Bedrooms10 Guests
New to Booking
$2069
Average price / night
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The Beach House Bailey Island Maine
The Beach House Bailey Island Maine
Apartment
Harpswell, ME, 04003, United States
1.8k from Paddleworks center

Balcony, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

2 Bedrooms6 Guests
10.0

Exceptional

35 reviews

$309
Average price / night
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Casco Breeze
Casco Breeze
House
North Harpswell, ME, USA
7.2k from Paddleworks center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
9.1

Superb

9 reviews

$582
Average price / night
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Private Ocean Front property with bathing cove and deep water swimming
Private Ocean Front property with bathing cove and deep water swimming
House
Harpswell, ME, 04079, United States
2.7k from Paddleworks center

Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
9.8

Exceptional

57 reviews

$280
Average price / night
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Harpswell Retreat
Harpswell Retreat
House
Cundys Harbor, ME, USA
8.0k from Paddleworks center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
7.8

Good

6 reviews

$593
Average price / night
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Grace's Place, a Real Maine Cottage
Grace's Place, a Real Maine Cottage
Cottage
harpswell, ME, 04079, United States
2.7k from Paddleworks center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms7 Guests
9.8

Exceptional

51 reviews

$316
Average price / night
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Fantastic Waterfront Views
Fantastic Waterfront Views
House
Phippsburg, ME, USA
9.2k from Paddleworks center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom8 Guests
9.3

Superb

3 reviews

$340
Average price / night
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Beautiful house on the Harpswell Peninsula over looking Casco Bay
Beautiful house on the Harpswell Peninsula over looking Casco Bay
House
Harpswell, ME, 04079, United States
2.9k from Paddleworks center

Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

7 Bedrooms15 Guests
9.6

Exceptional

74 reviews

$681
Average price / night
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Mermaid
Mermaid
House
Paddleworks, Orrs Island, Maine, USA
9.2k from Paddleworks center

Laundry, Kitchen, Balcony/Terrace, Parking, Internet, Child Friendly

3 Bedrooms12 Guests
New to Booking
$855
Average price / night
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Bay-View. Waterfront Log cabin on the bay. Pet Friendly.
Bay-View. Waterfront Log cabin on the bay. Pet Friendly.
Cabin
Harpswell, ME, 04079, United States
3.0k from Paddleworks center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.8

Exceptional

28 reviews

$508
Average price / night
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Nicest Waterfront in Maine w/ Private Beach!
Nicest Waterfront in Maine w/ Private Beach!
House
Harpswell, ME, 04003, United States
3.1k from Paddleworks center

Arcade, Balcony, Barbecue, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking, Heater

4 Bedrooms10 Guests
9.6

Exceptional

44 reviews

$1341
Average price / night
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Sunrise Catcher with a Panoramic View!
Sunrise Catcher with a Panoramic View!
House
Harpswell, ME, 04079, United States
3.1k from Paddleworks center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

51 reviews

$708
Average price / night
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Oceanfront 4 bed, 3 bath colonial beach home, right on Casco Bay!
Oceanfront 4 bed, 3 bath colonial beach home, right on Casco Bay!
House
Harpswell, ME, 04079, United States
3.8k from Paddleworks center

Arcade, Barbecue, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms13 Guests
9.8

Exceptional

39 reviews

$681
Average price / night
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The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
House
Harpswell, ME, 04079, United States
4.1k from Paddleworks center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

6 Bedrooms15 Guests
10.0

Exceptional

2 reviews

$1053
Average price / night
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Beautifully renovated 4BR, 2BA pet friendly home with ocean views and access
Beautifully renovated 4BR, 2BA pet friendly home with ocean views and access
House
Harpswell, ME, 04079, United States
4.2k from Paddleworks center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area

4 Bedrooms10 Guests
New to Booking
$663
Average price / night
Check Availability
700' OCEANFRONT RETREAT, FIRE PIT, 10 ACRES, 6 BR, 8 KAYAKS, 2 PDL BRDS,
700' OCEANFRONT RETREAT, FIRE PIT, 10 ACRES, 6 BR, 8 KAYAKS, 2 PDL BRDS,
House
Harpswell, ME, 04079, United States
4.2k from Paddleworks center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms16 Guests
10.0

Exceptional

52 reviews

$1798
Average price / night
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Howard Family Cottage with Casco Bay Sunset Views!
Howard Family Cottage with Casco Bay Sunset Views!
House
Harpswell, ME, 04079, United States
4.2k from Paddleworks center

Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

2 Bedrooms6 Guests
9.6

Exceptional

10 reviews

$284
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Paddleworks.

Paddleworks Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 61 verified family-friendly vacation rentals in Paddleworks. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Paddleworks vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $196 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Paddleworks offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Paddleworks are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Paddleworks often include amenities such as Child Friendly, Balcony/Terrace, and Fireplace/Heating. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.