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

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366 Best Vacation Rentals in Stroudwater (Starting from $93)

New Spacious Home Near Old Port and Downtown Portland
New Spacious Home Near Old Port and Downtown Portland
Apartment
Stroudwater, Portland, Maine, USA
1.9k from Stroudwater center

Air Conditioner, Parking, Internet, Child Friendly

2 Bedrooms6 Guests
New to Booking
$1232
Average price / night
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Nature with in-town living that feels a world away. May-June-July special!!!
Nature with in-town living that feels a world away. May-June-July special!!!
House
Portland, ME, 04102, United States
0.5k from Stroudwater center

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

3 Bedrooms6 Guests
8.6

Fabulous

20 reviews

$445
Average price / night
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Spacious & New 2 BD 3 BA High End House
Spacious & New 2 BD 3 BA High End House
Apartment
Stroudwater, Portland, Maine, USA
1.9k from Stroudwater center

Internet, Parking, Air Conditioner, Child Friendly

1 Bedroom8 Guests
New to Booking
$882
Average price / night
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Back yard paradise
Back yard paradise
House
Portland, ME, 04102, United States
0.5k from Stroudwater center

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

4 Bedrooms7 Guests
9.8

Exceptional

22 reviews

$505
Average price / night
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Luxury on Back Cove - Three Gables
Luxury on Back Cove - Three Gables
Apartment
Portland, ME, USA
2.3k from Stroudwater center

Fireplace/Heating, Air Conditioner, Guest Services, Internet, View, Sports/Activities, Security/Safety

3 Bedrooms6 Guests
New to Booking
$484
Average price / night
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Quiet, residential neighborhood
Quiet, residential neighborhood
Apartment
Portland, ME, 04102, United States
1.8k from Stroudwater center

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

1 Bedroom4 Guests
10.0

Exceptional

44 reviews

$270
Average price / night
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Oakdale Area Nice Location
Oakdale Area Nice Location
Apartment
ME, USA
3.2k from Stroudwater center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

2 Bedrooms4 Guests
9.0

Fabulous

1 reviews

$319
Average price / night
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Private Entrance Residential Portland
Private Entrance Residential Portland
Apartment
Portland, ME, USA
3.7k from Stroudwater center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$160
Average price / night
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Cozy home in Westbrook close to beaches and Portland.
Cozy home in Westbrook close to beaches and Portland.
House
Westbrook, ME, 04092, United States
2.5k from Stroudwater center

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

2 Bedrooms4 Guests
New to Booking
$1744
Average price / night
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Guest Space on the Portland Peninsula
Guest Space on the Portland Peninsula
Apartment
Portland, ME, USA
3.9k from Stroudwater center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Self-catering

1 Bedroom3 Guests
7.4

Good

6 reviews

$245
Average price / night
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Convenient, Modern Thompson s Point 3-Bed Flat
Convenient, Modern Thompson s Point 3-Bed Flat
Apartment
Portland, ME, 04102, United States
2.6k from Stroudwater center

Barbecue, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Microwave, No Smoking

3 Bedrooms6 Guests
9.4

Superb

24 reviews

$456
Average price / night
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Entire Historic Home - Portland West End
Entire Historic Home - Portland West End
House
Portland, ME, USA
3.9k from Stroudwater center

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

7 Bedrooms16 Guests
New to Booking
$886
Average price / night
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Rosemont 1st Fl: 2BR: Sunny Spacious Convenient
Rosemont 1st Fl: 2BR: Sunny Spacious Convenient
Apartment
Portland, ME, 04103, United States
2.7k from Stroudwater center

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

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$141
Average price / night
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Modern Getaway By The Sea
Modern Getaway By The Sea
House
South Portland, ME, USA
3.9k from Stroudwater center

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

3 Bedrooms6 Guests
New to Booking
$450
Average price / night
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Spacious 3 BR in Portland's Libbytown!
Spacious 3 BR in Portland's Libbytown!
Apartment
Portland, ME, 04102, United States
2.9k from Stroudwater center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
9.6

Exceptional

45 reviews

$406
Average price / night
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Knock on Wood - Airy Charm in Heart of Downtown
Knock on Wood - Airy Charm in Heart of Downtown
Apartment
Portland, ME, USA
4.1k from Stroudwater center

Fireplace/Heating, Air Conditioner, Guest Services, Internet, Pet Friendly, Security/Safety, Child Friendly

1 Bedroom6 Guests
New to Booking
$455
Average price / night
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Entire House Deering Highlands
Entire House Deering Highlands
House
Portland, ME, 04103, United States
3.1k from Stroudwater center

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

3 Bedrooms6 Guests
9.6

Exceptional

8 reviews

$554
Average price / night
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Skyline 138 Charming West End Mansard Penthouse
Skyline 138 Charming West End Mansard Penthouse
Apartment
Portland, ME, USA
4.1k from Stroudwater center

Fireplace/Heating, Air Conditioner, Guest Services, Laundry, Internet, View, Pet Friendly

3 Bedrooms8 Guests
New to Booking
$513
Average price / night
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Maine Social House/By Downtown/Balcony
Maine Social House/By Downtown/Balcony
House
Portland, ME, 04103, United States
3.1k from Stroudwater center

6 Bedrooms16 Guests
New to Booking
$1858
Average price / night
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Spacious Portland Home With Parking
Spacious Portland Home With Parking
House
Portland, ME, USA
4.2k from Stroudwater center

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

4 Bedrooms12 Guests
8.0

Good

1 reviews

$804
Average price / night
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Harmony House/Walk to Downtown/Parking/Balcony
Harmony House/Walk to Downtown/Parking/Balcony
House
Portland, ME, 04103, United States
3.2k from Stroudwater center

3 Bedrooms8 Guests
New to Booking
$612
Average price / night
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Hidden private one bedroom gem
Hidden private one bedroom gem
Apartment
Portland, ME, 04102, United States
3.3k from Stroudwater center

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

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$166
Average price / night
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Urban Ease/By Downtown/Parking
Urban Ease/By Downtown/Parking
House
Portland, ME, 04103, United States
3.4k from Stroudwater center

3 Bedrooms8 Guests
New to Booking
$661
Average price / night
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The Portland Getaway\n
The Portland Getaway\n
Apartment
Portland, ME, 04102, United States
3.4k from Stroudwater center

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

3 Bedrooms6 Guests
9.6

Exceptional

34 reviews

$340
Average price / night
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New England Charm, Portland - Parking included
New England Charm, Portland - Parking included
Apartment
Portland, ME, 04103, United States
3.5k from Stroudwater center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Toys

3 Bedrooms6 Guests
10.0

Exceptional

18 reviews

$471
Average price / night
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Nesting Haven: Your Cozy Escape
Nesting Haven: Your Cozy Escape
Apartment
Portland, ME, 04103, United States
3.5k from Stroudwater center

AC, Internet, Kitchen, No Smoking, TV

New to Booking
$115
Average price / night
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The Portland Perch – Ideal for Extended Stays!
The Portland Perch – Ideal for Extended Stays!
Apartment
Portland, ME, 04103, United States
3.5k from Stroudwater center

AC, Internet, Kitchen, No Smoking, TV

1 Bedroom2 Guests
New to Booking
$93
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 Stroudwater.

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Frequently Asked Questions

You can explore 366 verified vacation rentals in Stroudwater. 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 Stroudwater vary depending on the season, property size, and location. Rates typically start from around $93 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 Stroudwater 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 Stroudwater welcome pets. Currently, 38 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 Stroudwater often include amenities such as Internet, Fireplace/Heating, and Child Friendly. 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.