Vacation Rentals in Harborside, ME: Compare 10+ Sites & Save

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61 Best Vacation Rentals in Harborside (Starting from $150)

Quarters on Main
Quarters on Main
House
Castine, ME, USA
4.6k from Harborside center

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

1 Bedroom12 Guests
New to Booking
$585
Average price / night
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Sweet cottage on Cape Rosier
Sweet cottage on Cape Rosier
House
Brooksville, ME, 04642, United States
1.6k from Harborside center

Arcade, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

20 reviews

$219
Average price / night
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Lobster Tail Cottage
Lobster Tail Cottage
House
Castine, ME, USA
6.7k from Harborside center

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

3 Bedrooms7 Guests
8.5

Very Good

2 reviews

$259
Average price / night
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Charming 1-bedroom cottage in Cape Rosier
Charming 1-bedroom cottage in Cape Rosier
Cottage
Brooksville, ME, 04642, United States
1.8k from Harborside center

Barbecue, Heater, Kitchen, Living Area, No Smoking, Outdoor Space

1 Bedroom3 Guests
New to Booking
$150
Average price / night
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Bayside Dreams
Bayside Dreams
House
Castine, ME, USA
6.8k from Harborside center

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

2 Bedrooms5 Guests
New to Booking
$383
Average price / night
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Waterfront Cottage on Beautiful Horseshoe Cove, Cape Rosier, Brooksville
Waterfront Cottage on Beautiful Horseshoe Cove, Cape Rosier, Brooksville
Cottage
Brooksville, ME, 04642, United States
3.0k from Harborside center

Heater, No Smoking

1 Bedroom2 Guests
8.0

Good

1 reviews

$234
Average price / night
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Kayaker's paradise at Piper's Nest Cottage overlooking Smith Cove
Kayaker's paradise at Piper's Nest Cottage overlooking Smith Cove
Cottage
Brooksville, ME, 04642, United States
3.1k from Harborside center

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

5 Bedrooms12 Guests
9.8

Exceptional

40 reviews

$350
Average price / night
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 Boathouse Cabin on Horseshoe Cove, Cape Rosier, Brooksville, Maine
Boathouse Cabin on Horseshoe Cove, Cape Rosier, Brooksville, Maine
Cabin
Brooksville, ME, 04642, United States
3.2k from Harborside center

Heater, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

3 reviews

$163
Average price / night
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Cape Rosier, Maine 6 bedroom estate on Penobscot Bay. West views over Camden the hills
Cape Rosier, Maine 6 bedroom estate on Penobscot Bay. West views over Camden the hills
House
Brooksville, ME, 04642, United States
3.7k from Harborside center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Living Area, No Smoking, Patio

6 Bedrooms13 Guests
9.4

Superb

16 reviews

$1884
Average price / night
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Quaint Waterfront Cottage
Quaint Waterfront Cottage
Cottage
Brooksville, ME, 04642, United States
3.9k from Harborside center

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

3 Bedrooms6 Guests
9.2

Superb

31 reviews

$366
Average price / night
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Secluded Oceanfront Cabin With Private Cove and Beach
Secluded Oceanfront Cabin With Private Cove and Beach
Cabin
Brooksville, ME, 04617, United States
4.1k from Harborside center

Free Parking, Internet, Kitchen, Microwave, No Smoking, Patio, Toys

3 Bedrooms6 Guests
10.0

Exceptional

57 reviews

$327
Average price / night
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Village Cottage with an Amazing Water View
Village Cottage with an Amazing Water View
Cottage
Castine, ME, 04421, United States
4.1k from Harborside center

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

2 Bedrooms6 Guests
9.6

Exceptional

76 reviews

$241
Average price / night
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Large Cottage w Ocean Views.
Large Cottage w Ocean Views.
Cottage
castine, ME, 04421, United States
4.1k from Harborside center

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

5 Bedrooms12 Guests
9.4

Superb

23 reviews

$501
Average price / night
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Capacious Coastal Villa for Memorable Moments Along Coast of Maine
Capacious Coastal Villa for Memorable Moments Along Coast of Maine
House
Castine, ME, 04421, United States
4.1k from Harborside center

AC, Arcade, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking

10 Bedrooms22 Guests
9.6

Exceptional

12 reviews

$913
Average price / night
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Spacious Cottage in  Castine
Spacious Cottage in Castine
House
Castine, ME, 04421, United States
4.1k from Harborside center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

4 Bedrooms6 Guests
10.0

Exceptional

13 reviews

$489
Average price / night
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1930's Private Oceanfront Cottage
1930's Private Oceanfront Cottage
Cottage
Brooksville, ME, 04617, United States
4.2k from Harborside center

Fireplace, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio, Toys

3 Bedrooms7 Guests
10.0

Exceptional

15 reviews

$343
Average price / night
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Charming two-bedroom cottage on Cape Rosier walking distance to Bakeman Beach!
Charming two-bedroom cottage on Cape Rosier walking distance to Bakeman Beach!
Cottage
Brooksville, ME, 04642, United States
4.4k from Harborside center

Barbecue, Dryer, Fireplace, Heater, Internet, Laundry, Microwave, No Smoking, Washer

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$288
Average price / night
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Stunning Tiny House -as if Below Decks on a Yacht! Sailing inspired interior.
Stunning Tiny House -as if Below Decks on a Yacht! Sailing inspired interior.
Cottage
Castine, ME, 04421, United States
4.4k from Harborside center

Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Grill

1 Bedroom4 Guests
10.0

Exceptional

4 reviews

$242
Average price / night
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Guest Manse “Carriage House” with Harbor Views
Guest Manse “Carriage House” with Harbor Views
House
Castine, ME, 04421, United States
4.4k from Harborside center

Arcade, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$414
Average price / night
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Experience One Of The Oldest Houses In Castine
Experience One Of The Oldest Houses In Castine
House
Castine, ME, 04421, United States
4.6k from Harborside center

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

4 Bedrooms4 Guests
10.0

Exceptional

30 reviews

$517
Average price / night
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Friendly home with our separate condos & free WiFi in the heart of downtown
Friendly home with our separate condos & free WiFi in the heart of downtown
House
Castine, ME, 04421, United States
4.6k from Harborside center

Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking

6 Bedrooms12 Guests
New to Booking
$1049
Average price / night
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Downtown Studio w/ Full Kitchen & Shared Porch - Walk Everywhere in Town
Downtown Studio w/ Full Kitchen & Shared Porch - Walk Everywhere in Town
Apartment
Castine, ME, 04421, United States
4.6k from Harborside center

Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
7.8

Good

9 reviews

$250
Average price / night
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Comfortable Castine getaway w/ a full kitchen - walk to the waterfront
Comfortable Castine getaway w/ a full kitchen - walk to the waterfront
Apartment
Castine, ME, 04421, United States
4.6k from Harborside center

Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
8.6

Fabulous

9 reviews

$314
Average price / night
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Casa Calypsu-a waterfront retreat on Horseshoe Cove
Casa Calypsu-a waterfront retreat on Horseshoe Cove
House
Brooksville, ME, 04617, United States
4.7k from Harborside center

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

4 Bedrooms12 Guests
New to Booking
$421
Average price / night
Check Availability
Lovely Cape Rosier Waterfront Cottage
Lovely Cape Rosier Waterfront Cottage
Cottage
Brooksville, ME, 04617, United States
4.7k from Harborside center

Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms5 Guests
10.0

Exceptional

31 reviews

$288
Average price / night
Check Availability
In The Heart Of Castine, 3 blocks from docks, perfect for family reunions
In The Heart Of Castine, 3 blocks from docks, perfect for family reunions
House
Castine, ME, 04421, United States
4.8k from Harborside center

Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

5 Bedrooms12 Guests
10.0

Exceptional

36 reviews

$657
Average price / night
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Beach Front in Magical Cape Rosier\nNewly renovated.
Beach Front in Magical Cape Rosier\nNewly renovated.
Ski Chalet
Harborside, ME, 04642, United States
4.8k from Harborside center

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

3 Bedrooms6 Guests
10.0

Exceptional

69 reviews

$347
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 Vacation Rentals in Harborside.

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Frequently Asked Questions

You can explore 61 verified vacation rentals in Harborside. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Harborside vary depending on the season, property size, and location. Rates typically start from around $150 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Harborside include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Harborside welcome pets. Currently, 28 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Harborside often include amenities such as Fireplace/Heating, Kitchen, and Balcony/Terrace. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.