Maui Dream Wedding - Vacation Rentals in Stroudwater

The Chadwick Bed and Breakfast From US $349
         

|
9.2 (29 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
The Westin Portland Harborview From US $262
         

|
9.0 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
West End 2nd Floor Apartment 762 Congress Street From US $258
         

9.0 (39 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
5 Star Back Cove Apartment with water view! From US $392
         

10.0 (157 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Completely remodeled 2 bedroom apartment in Portland's West End From US $671
         

10.0 (78 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
2 Bedroom Apartment on Top Floor in Portland's West End From US $547
         

10.0 (74 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Stroudwater

Over 457+ Luxury Places to Stay in or Near Stroudwater
Stunning Entire Three Units Apts (USM AREA) From US $2,225
         

10.0 (31 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Entire Home | Sleeps 16 | w/Roof Deck | 5 mins to Downtown From US $1,914
         

7 Bed Historic Home for Group Stays From US $1,729
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Maine Social House/By Downtown/Balcony From US $1,726
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Top-Rated Vacation Rentals with a Pool in Stroudwater

Over 84+ Top-Rated Vacation Rentals with a Pool in or Near Stroudwater
Back yard paradise From US $636
         

9.8 (23 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Homewood Suites by Hilton Portland From US $285
         

|
9.3 (125 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
TownePlace Suites Portland Airport ME From US $200
         

|
8.9 (124 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • Private Pool
Holiday Inn Portland-By the Bay by IHG From US $180
         

|
8.5 (1029 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hampton Inn & Suites Portland West From US $196
         

|
8.4 (824 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Best Western Merry Manor Inn From US $114
         

|
8.2 (541 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Stroudwater

Over 159+ Pet-Friendly Vacation Rentals in or Near Stroudwater
Brand New 1 Bedroom Apartment in Portland From US $543
         

10.0 (45 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
State of Charm - Historic West End Haven From US $579
         

|
9.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
New England Charm, Portland - Parking included From US $456
         

10.0 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy 3BR | Pet Friendly | Near Portland | Parking From US $396
         

10.0 (13 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Romantic apt:West End +parking From US $495
         

10.0 (9 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Rare West End Home Walk to Old Port, Harbor View From US $653
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Soaking Tub | W/D | Parking | 5 Min Downtown From US $590
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11 From US $747
         

Large Vacation Homes & Villas in Stroudwater

Over 44+ Large Vacation Homes & Villas in or Near Stroudwater
Huge Historic Downtown Townhome From US $868
         

9.8 (10 Reviews)
Villa
  • Air Conditioner
  • Parking
  • TV
The West End Collection on Pine From US $459
         

|
9.1 (81 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Spacious Portland Home + Parking From US $788
         

9.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Modern West End 2 Bedroom Apartment From US $567
         

7.8 (28 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
4BR/3BA Near Old Port + Parking! From US $654
         

New
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Sleeps 10 | 2 Kitchens | Near Back Cove | Parking From US $593
         

Wheelchair Accessible Vacation Homes in Stroudwater

Over 112+ Wheelchair Accessible Vacation Homes in or Near Stroudwater
HomeAwhile From US $142
         

9.6 (5 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Fairfield by Marriott Inn & Suites Portland Maine Airport From US $133
         

Peaceful Stay | Minutes from Downtown Excitement From US $334
         

6.0 (2 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Stroudwater Vacation Rentals and Airbnb Places to Stay Under $200

Over 103+ Stroudwater Vacation Rentals and Airbnb Places to Stay Under $200
Simple & Convenient Downtown Living From US $130
         

|
8.5 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
DoubleTree by Hilton Hotel Portland From US $178
         

|
8.0 (1402 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Stunning - modern 2 bedroom Victorian mansion pad From US $177
         

10.0 (2 Reviews)
House
  • Security/Safety
  • Bedding/Linens
  • Child Friendly
Ultra cool new modern flat From US $164
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Security/Safety
Back Cove Charmer Close to Everything From US $164
         

9.2 (85 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming private 1st floor studio apartment From US $160
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Bright and Cozy, 1 BR/1 BA Retreat in South Portland From US $153
         

Instantly Bookable Vacation Homes in Stroudwater

Over 218+ Instantly Bookable Vacation Homes in or Near Stroudwater
Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist From US $581
         

10.0 (56 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Charming West End Hideaway. Private Parking From US $318
         

10.0 (51 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Bright & Sunny West End Apartment with Private Parking. From US $434
         

Near Portland Trails: Walkable Apartment w/Deck From US $378
         

10.0 (50 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Stylish Brownstone Downtown Free St|Perfect Getaway for 2 From US $450
         

10.0 (41 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
West End Bright Spot with Parking. From US $370
         

10.0 (22 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Newly Renovated 2nd Floor Apt near USM From US $664
         

10.0 (16 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About Stroudwater Vacation Rentals

With more than 466 Stroudwater vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Mauidreamwedding and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Stroudwater.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Mauidreamwedding Stroudwater, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Stroudwater. Places to stay near Stroudwater are 1059.19 ft² on average, with prices averaging US $476 a night.

Mauidreamwedding makes it easy and safe to find and compare vacation rentals in Stroudwater with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Stroudwater

Type Count
Holiday Apartments 180
Vacation Homes 131
Hotels 117
B&B 9
Villas 2
Cottages 1
Hostels 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Stroudwater

Pro Tip: Mauidreamwedding makes it easy to compare the best listings on Mauidreamwedding homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Mauidreamwedding homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Stroudwater.

Weather in Stroudwater

View the weather forecast for Stroudwater before booking your Stroudwater Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Other Places to Stay Near Stroudwater, ME


Complexes around Stroudwater, ME


Stroudwater Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Stroudwater?
How many vacation rentals are available in Stroudwater?

Currently, the total number of properties listed in 2026 is over 466 in the Stroudwater area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Stroudwater.