Cottage Rentals in Squirrel Island, ME: Compare 10+ Sites & Save

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100 Best Cottage Rentals in Squirrel Island (Starting from $201)

Charming Two-Bedroom Ocean-View Cottage in Quiet Southport
Charming Two-Bedroom Ocean-View Cottage in Quiet Southport
Cottage
Southport, ME, 04576, United States
2.1k from Squirrel Island center

Balcony, Fireplace, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
New to Booking
$201
Average price / night
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Ocean front cottage on a drive-on island in Boothbay Harbor, Maine
Ocean front cottage on a drive-on island in Boothbay Harbor, Maine
Cottage
Southport, ME, 04576, United States
2.1k from Squirrel Island center

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

5 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$1261
Average price / night
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Colburn Cottage - Downstairs - Waterfront + Beach!!
Colburn Cottage - Downstairs - Waterfront + Beach!!
Cottage
Southport, ME, 04576, United States
2.2k from Squirrel Island center

Free Parking, Internet, Kitchen, No Smoking

2 Bedrooms4 Guests
New to Booking
$332
Average price / night
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Ship's Wheel - Charming Ocean View in Ocean Point!
Ship's Wheel - Charming Ocean View in Ocean Point!
Cottage
East Boothbay, ME, 04544, United States
2.3k from Squirrel Island center

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

2 Bedrooms4 Guests
10.0

Exceptional

23 reviews

$435
Average price / night
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Come and enjoy our Boothbay Cottage
Come and enjoy our Boothbay Cottage
Cottage
Boothbay Harbor, ME, 04538, United States
2.4k from Squirrel Island center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms4 Guests
10.0

Exceptional

49 reviews

$365
Average price / night
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Thrush Cottage - Cozy 2BDR with Water Views -Original Spruce Point Inn Cottage!
Thrush Cottage - Cozy 2BDR with Water Views -Original Spruce Point Inn Cottage!
Cottage
Boothbay Harbor, ME, 04538, United States
2.4k from Squirrel Island center

Free Parking, Internet, Kitchen, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

5 reviews

$387
Average price / night
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Ocean Point Colony Home w/ Sunroom & Sweeping Ocean Views, Dog-friendly
Ocean Point Colony Home w/ Sunroom & Sweeping Ocean Views, Dog-friendly
Cottage
East Boothbay, ME, 04544, United States
2.5k from Squirrel Island center

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

4 Bedrooms9 Guests
8.8

Fabulous

39 reviews

$722
Average price / night
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Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
Cottage
East Boothbay, ME, 04544, United States
2.6k from Squirrel Island center

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

4 Bedrooms10 Guests
9.2

Superb

70 reviews

$669
Average price / night
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Just one block from the Ocean!
Just one block from the Ocean!
Cottage
East Boothbay, ME, 04544, United States
2.6k from Squirrel Island center

Barbecue, Dryer, Extra Bed, Fireplace, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
9.2

Superb

15 reviews

$460
Average price / night
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Ocean Point home, large porch, ocean view, water access
Ocean Point home, large porch, ocean view, water access
Cottage
East Boothbay, ME, 04544, United States
2.7k from Squirrel Island center

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

4 Bedrooms7 Guests
9.2

Superb

21 reviews

$477
Average price / night
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Ocean Point-4 bedrooms, 2 full baths - \"Peace Restored\"
Ocean Point-4 bedrooms, 2 full baths - \"Peace Restored\"
Cottage
Boothbay, ME, 04544, United States
2.8k from Squirrel Island center

Crib, Dryer, Fireplace, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
9.2

Superb

5 reviews

$298
Average price / night
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Serene Southport Island: Private dock, spectacular views, near Boothbay Harbor.
Serene Southport Island: Private dock, spectacular views, near Boothbay Harbor.
Cottage
Southport, ME, 04576, United States
2.8k from Squirrel Island center

Dryer, Heater, Laundry, No Smoking, Washer

4 Bedrooms7 Guests
New to Booking
$840
Average price / night
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Cottage at Island Point; Charming Coastal Retreat
Cottage at Island Point; Charming Coastal Retreat
Cottage
Southport, ME, 04576, United States
2.9k from Squirrel Island center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$418
Average price / night
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Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Dog-Friendly
Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Dog-Friendly
Cottage
East Boothbay, ME, 04544, United States
2.9k from Squirrel Island center

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

1 Bedroom3 Guests
9.6

Exceptional

29 reviews

$401
Average price / night
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Charming Cottage: Deepwater Dock, Panoramic Linekin Bay Views, Near Village
Charming Cottage: Deepwater Dock, Panoramic Linekin Bay Views, Near Village
Cottage
East Boothbay, ME, 04544, United States
2.9k from Squirrel Island center

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

2 Bedrooms6 Guests
9.2

Superb

12 reviews

$575
Average price / night
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2 Waterfront Cottages in Ocean Point with Dock & Large Yard, Dog friendly
2 Waterfront Cottages in Ocean Point with Dock & Large Yard, Dog friendly
Cottage
East Boothbay, ME, 04544, United States
3.0k from Squirrel Island center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Kitchen, Living Area

3 Bedrooms9 Guests
6.0

Review score

1 reviews

$959
Average price / night
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Oceanfront  Cottage Southport 3 BR 2BA, Handicapped Accessible
Oceanfront Cottage Southport 3 BR 2BA, Handicapped Accessible
Cottage
Southport, ME, 04576, United States
3.1k from Squirrel Island center

Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.2

Superb

49 reviews

$314
Average price / night
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Year Round Charming & Cozy Cottage at Ocean Point
Year Round Charming & Cozy Cottage at Ocean Point
Cottage
east boothbay, ME, 04544, United States
3.1k from Squirrel Island center

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

2 Bedrooms4 Guests
10.0

Exceptional

60 reviews

$347
Average price / night
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All Aboard Cottage
All Aboard Cottage
Cottage
East Boothbay, ME, 04544, United States
3.1k from Squirrel Island center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$530
Average price / night
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Cozy 2-bedroom cottage located in the heart of inner Boothbay Harbor.
Cozy 2-bedroom cottage located in the heart of inner Boothbay Harbor.
Cottage
Boothbay Harbor, ME, 04553, United States
3.2k from Squirrel Island center

AC, Heater, Internet

2 Bedrooms4 Guests
New to Booking
$274
Average price / night
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Charming 3-bedroom cottage in Southport with water views and close to Boothbay.
Charming 3-bedroom cottage in Southport with water views and close to Boothbay.
Cottage
Southport, ME, 04576, United States
3.3k from Squirrel Island center

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

3 Bedrooms6 Guests
9.2

Superb

5 reviews

$279
Average price / night
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Linekin Vista - 3BDR Waterfront Cottage on Linekin Bay with Private Beach!
Linekin Vista - 3BDR Waterfront Cottage on Linekin Bay with Private Beach!
Cottage
East Boothbay, ME, 04544, United States
3.3k from Squirrel Island center

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

3 Bedrooms6 Guests
9.8

Exceptional

37 reviews

$540
Average price / night
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Ocean views, private beach, garden patio, red clay tennis, dock access, WiFi
Ocean views, private beach, garden patio, red clay tennis, dock access, WiFi
Cottage
Boothbay Harbor, ME, 04538, United States
3.5k from Squirrel Island center

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

2 Bedrooms4 Guests
New to Booking
$356
Average price / night
Check Availability
Gorgeous Views of Harbor Entrance! Walk to town, east side location.
Gorgeous Views of Harbor Entrance! Walk to town, east side location.
Cottage
Boothbay Harbor, ME, 04538, United States
3.5k from Squirrel Island center

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

2 Bedrooms6 Guests
9.8

Exceptional

31 reviews

$344
Average price / night
Check Availability
Classic Maine Cottage with ocean views
Classic Maine Cottage with ocean views
Cottage
West Boothbay Harbor, ME, 04575, United States
3.6k from Squirrel Island center

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

4 Bedrooms8 Guests
9.8

Exceptional

40 reviews

$386
Average price / night
Check Availability
Romley House | Deck & New Luxe Kitchen | Near Boothbay Harbor
Romley House | Deck & New Luxe Kitchen | Near Boothbay Harbor
Cottage
Southport Island, ME, 04576, United States
3.6k from Squirrel Island center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
9.8

Exceptional

48 reviews

$359
Average price / night
Check Availability
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access Dog-friendly
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access Dog-friendly
Cottage
Boothbay Harbor, ME, 04538, United States
3.7k from Squirrel Island center

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

3 Bedrooms8 Guests
9.6

Exceptional

73 reviews

$393
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 Cottage Rentals in Squirrel Island.

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Frequently Asked Questions

You can explore 100 verified cottage rentals in Squirrel Island. Our listings are sourced from a range of trusted booking providers, giving you access to charming coastal cottages, peaceful countryside escapes, and cozy stays—all in one place.

Cottage rental prices in Squirrel Island vary based on the season, location, and amenities offered. Rates typically start from around $201 per night, with higher prices during peak travel periods or in waterfront locations. Comparing different options can help you find a stay that fits both your preferences and budget.

Many cottages in Squirrel Island feature inviting outdoor areas such as private gardens, patios, or small yards. These spaces are ideal for relaxing, dining outdoors, or enjoying the surrounding scenery. You can use the available filters to quickly find cottages with outdoor features that match your preferences.

Yes, cottages are often a great choice for travelers with pets thanks to their cozy layouts and access to outdoor space. Currently, 18 listings in Squirrel Island welcome pets, making it easier to plan a comfortable stay with your companion.

For busy seasons such as summer holidays or long weekends, it’s a good idea to book your cottage 60 to 90 days in advance. Since cottages are typically smaller and more unique, the most desirable options tend to get reserved quickly during peak periods.

Cottages in Squirrel Island are known for their comfort and charm, often including amenities such as Bedding/Linens, Kitchen, and Fireplace/Heating. These features help create a relaxing and home-like atmosphere for guests.

Yes, many cottages in Squirrel Island are well-suited for longer stays. They often include essentials like full kitchens, laundry facilities, and comfortable living spaces, making them a practical option for extended vacations or remote work.