1+ Vacation Rentals Near Stroudwater |
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Big Pine Resort Cottages - Vacation Rentals in Stroudwater

Charming 2-Story Cottage with Hot Tub, Near Downtown and Back Cove. From US $320
         

10.0 (14 Reviews)
Cottage
Charming 2-Story Cottage with Hot Tub, Near Downtown and Back Cove.
  • Air Conditioner
  • Parking
  • TV

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Luxury Places to Stay in Stroudwater

Over 452+ Luxury Places to Stay in or Near Stroudwater
Charming Historic Estate | Perfect for Wedding Headquarters, Groups & Events From US $2,504
         

New
House
Charming Historic Estate | Perfect for Wedding Headquarters, Groups & Events
  • Air Conditioner
  • Parking
  • TV

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Prime central Location Large Deck Walk to Old Port,Waterfront & music venues From US $2,128
         

10.0 (2 Reviews)
House
Prime central Location Large Deck Walk to Old Port,Waterfront & music venues
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Entire Home | Sleeps 16 | w/Roof Deck | 5 mins to Downtown From US $1,829
         

10.0 (1 Review)
House
Entire Home | Sleeps 16 | w/Roof Deck | 5 mins to Downtown
  • Air Conditioner
  • Pet Friendly
  • TV

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Stunning Entire Three Units Apts (USM AREA) From US $1,770
         

10.0 (30 Reviews)
Apartment
Stunning Entire Three Units Apts (USM AREA)
  • Air Conditioner
  • Parking
  • TV

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6BR | Sleeps 16 | Balcony | 10 mins to Downtown From US $1,678
         

New
House
6BR | Sleeps 16 | Balcony | 10 mins to Downtown
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hobson's Landing Condo in the heart of Portland's Historic Old Port Exchange From US $1,660
         

New
Condo
Hobson's Landing Condo in the heart of Portland's Historic Old Port Exchange
  • Air Conditioner
  • Parking
  • Pet Friendly

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West End Chic - Chef's Kitchen, Pool Table, W/D From US $1,247
         

New
House
West End Chic - Chef's Kitchen, Pool Table, W/D
  • Air Conditioner
  • Parking
  • TV

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New Spacious Home Near Old Port and Downtown Portland From US $1,232
         

New
Apartment
New Spacious Home Near Old Port and Downtown Portland
  • Air Conditioner
  • Parking
  • Child Friendly

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Top-Rated Vacation Rentals with a Pool in Stroudwater

Over 87+ Top-Rated Vacation Rentals with a Pool in or Near Stroudwater
Spacious Queen Suite, La Quinta, Shuttle Service, Minutes to The Arts District From US $123
         

10.0 (2 Reviews)
Hotel
Spacious Queen Suite, La Quinta, Shuttle Service, Minutes to The Arts District
  • Air Conditioner
  • Parking
  • Pool

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Back yard paradise From US $437
         

9.8 (22 Reviews)
House
Back yard paradise
  • Air Conditioner
  • Parking
  • Pool

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Inn at Park Spring 1 - Self Check In - Parking From US $121
         

9.6 (43 Reviews)
Hotel
Inn at Park Spring 1 - Self Check In - Parking
  • Air Conditioner
  • Parking
  • Pool

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Embassy Suites by Hilton Portland Maine From US $114
         

|
9.4 (1155 Reviews)
Hotel
Embassy Suites by Hilton Portland Maine
  • Air Conditioner
  • Parking
  • Pool

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Homewood Suites by Hilton Portland From US $106
         

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9.4 (1003 Reviews)
Hotel
Homewood Suites by Hilton Portland
  • Air Conditioner
  • Parking
  • Pool

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Homewood Suites by Hilton Portland From US $277
         

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9.1 (119 Reviews)
Hotel
Homewood Suites by Hilton Portland
  • Air Conditioner
  • Parking
  • Pet Friendly

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Holiday Inn Express Hotel & Suites South Portland by IHG From US $92
         

9.0 (1003 Reviews)
Hotel
Holiday Inn Express Hotel & Suites South Portland by IHG
  • Air Conditioner
  • Parking
  • Pool

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Courtyard by Marriott Portland Airport From US $92
         

|
9.0 (1002 Reviews)
Hotel
Courtyard by Marriott Portland Airport
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Vacation Rentals in Stroudwater

Over 158+ Pet-Friendly Vacation Rentals in or Near Stroudwater
Bright and Fresh Back Cove4 Bedroom, Sleeps 8. Airmatress for additional 2. From US $328
         

9.6 (75 Reviews)
Apartment
Bright and Fresh Back Cove4 Bedroom, Sleeps 8. Airmatress for additional 2.
  • Pet Friendly
  • TV
  • Balcony/Terrace

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The Heart of the West End #3 From US $464
         

|
9.4 (5 Reviews)
Apartment
The Heart of the West End #3
  • Pet Friendly
  • Security/Safety
  • Sports/Activities

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West End 2nd Floor Apartment 762 Congress Street From US $188
         

9.0 (39 Reviews)
Apartment
West End 2nd Floor Apartment 762 Congress Street
  • Air Conditioner
  • Parking
  • Pet Friendly

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Completely remodeled 2 bedroom apartment in Portland's West End From US $398
         

10.0 (78 Reviews)
Apartment
Completely remodeled 2 bedroom apartment in Portland's West End
  • Air Conditioner
  • Parking
  • Pet Friendly

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New England Charm, Portland - Parking included From US $410
         

10.0 (18 Reviews)
Apartment
New England Charm, Portland - Parking included
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cozy 3BR | Pet Friendly | Near Portland | Parking From US $282
         

10.0 (12 Reviews)
Apartment
Cozy 3BR | Pet Friendly | Near Portland | Parking
  • Air Conditioner
  • Pet Friendly
  • TV

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7 Bed Historic Home for Group Stays From US $1,115
         

10.0 (11 Reviews)
House
7 Bed Historic Home for Group Stays
  • Air Conditioner
  • Parking
  • Pet Friendly

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Romantic apt:West End +parking From US $548
         

10.0 (9 Reviews)
Condo
Romantic apt:West End +parking
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Stroudwater

Over 43+ Large Vacation Homes & Villas in or Near Stroudwater
Two Beautiful apartment From US $791
         

10.0 (25 Reviews)
House
Two Beautiful apartment
  • Air Conditioner
  • Parking
  • TV

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West End Inn From US $459
         

|
9.3 (117 Reviews)
Bed & Breakfast
West End Inn
  • Air Conditioner
  • Parking
  • Breakfast

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Toast to 2026! Free Champagne for all Jan/Feb Bookings From US $264
         

10.0 (4 Reviews)
House
Toast to 2026! Free Champagne for all Jan/Feb Bookings
  • Parking
  • Pet Friendly
  • TV

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SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11 From US $665
         

10.0 (1 Review)
House
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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WOW! Amazing New Coastal Escape + Hot Tub+Fire Pit From US $550
         

9.2 (7 Reviews)
House
WOW! Amazing New Coastal Escape + Hot Tub+Fire Pit
  • Air Conditioner
  • Parking
  • TV

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Centrally located off Back Cove, 1st floor 4 bedroom, 1.5 Bath condo w/porch From US $679
         

9.0 (2 Reviews)
Condo
Centrally located off Back Cove, 1st floor 4 bedroom, 1.5 Bath condo w/porch
  • Air Conditioner
  • Pet Friendly
  • TV

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Spacious Portland Home + Parking From US $377
         

9.0 (2 Reviews)
House
Spacious Portland Home + Parking
  • Air Conditioner
  • Parking
  • TV

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Modern West End 2 Bedroom Apartment From US $472
         

7.8 (28 Reviews)
Apartment
Modern West End 2 Bedroom Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

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Wheelchair Accessible Vacation Homes in Stroudwater

Over 113+ Wheelchair Accessible Vacation Homes in or Near Stroudwater
Central Room in Portland | Couple Stay w/Complimentary Breakfast From US $115
         

9.0 (2 Reviews)
Hotel
Central Room in Portland | Couple Stay w/Complimentary Breakfast
  • Air Conditioner
  • Parking
  • Pool

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The Francis Hotel From US $536
         

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9.0 (233 Reviews)
Hotel
The Francis Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

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Longfellow Hotel From US $170
         

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9.6 (142 Reviews)
Hotel
Longfellow Hotel
  • Air Conditioner
  • Parking
  • TV

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Elegant King Suite, La Quinta Portland, Downtown Proximity, Free Breakfast From US $121
         

8.0 (1 Review)
Hotel
Elegant King Suite, La Quinta Portland, Downtown Proximity, Free Breakfast
  • Air Conditioner
  • Parking
  • Pool

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Peaceful Stay | Minutes from Downtown Excitement From US $129
         

6.0 (2 Reviews)
Hotel
Peaceful Stay | Minutes from Downtown Excitement
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Accommodation Perfect for Portland Family Adventures, 2 Rooms From US $259
         

New
Hotel
Pet-Friendly Accommodation Perfect for Portland Family Adventures, 2 Rooms
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  • Parking
  • Pool

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Downtown Portland Escape, 2 Queen Beds, La Quinta, 2 Family Ready Rooms From US $259
         

New
Hotel
Downtown Portland Escape, 2 Queen Beds, La Quinta, 2 Family Ready Rooms
  • Air Conditioner
  • Parking
  • Pool

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Queen Comfort Room, La Quinta Wyndham, Breakfast Included, Close to Downtown From US $115
         

New
Hotel
Queen Comfort Room, La Quinta Wyndham, Breakfast Included, Close to Downtown
  • Air Conditioner
  • Parking
  • Pool

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Stroudwater Varoom and Airbnb Places to Stay Under $200

Over 161+ Stroudwater Varoom and Airbnb Places to Stay Under $200
Charming West End Hideaway. Private Parking From US $170
         

10.0 (47 Reviews)
Apartment
Charming West End Hideaway. Private Parking
  • Air Conditioner
  • Parking
  • TV

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Private Entrance Residential Portland From US $160
         

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9.0 (3 Reviews)
Apartment
Private Entrance Residential Portland
  • Air Conditioner
  • Parking
  • Pet Friendly

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Blind Tiger Portland – Carleton Street From US $195
         

|
9.6 (120 Reviews)
Bed & Breakfast
Blind Tiger Portland – Carleton Street
  • Air Conditioner
  • Balcony/Terrace
  • Accessibility

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Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN. From US $141
         

10.0 (5 Reviews)
House
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
  • Air Conditioner
  • Parking
  • TV

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Location, location! Prime- West End Studio. Walkable to entire city! From US $197
         

10.0 (2 Reviews)
Apartment
Location, location! Prime- West End Studio. Walkable to entire city!
  • Air Conditioner
  • TV
  • View

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Stunning - modern 2 bedroom Victorian mansion pad From US $177
         

10.0 (2 Reviews)
House
Stunning - modern 2 bedroom Victorian mansion pad
  • Security/Safety
  • Bedding/Linens
  • Child Friendly

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Charming 2-Bedroom Back Cove Retreat From US $187
         

10.0 (1 Review)
Apartment
Charming 2-Bedroom Back Cove Retreat
  • Air Conditioner
  • Parking
  • TV

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A Cozy 1 Bedroom Gem You'll LOVE!nSleeps 4, Pet Friendly, With Parking,
New
From US $175
         

10.0 (1 Review)
Apartment
A Cozy 1 Bedroom Gem You'll LOVE!nSleeps 4, Pet Friendly, With Parking,
  • Air Conditioner
  • Parking
  • Pet Friendly

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Instantly Bookable Vacation Homes in Stroudwater

Over 217+ Instantly Bookable Vacation Homes in or Near Stroudwater
Prime Location.Private Rooftop Deck.Walk to Old Port,Waterfront, Museum & Music From US $379
         

9.2 (28 Reviews)
Apartment
Prime Location.Private Rooftop Deck.Walk to Old Port,Waterfront, Museum & Music
  • Air Conditioner
  • TV
  • View

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WOW! Coastal Getaway: Hot Tub+FirePit+ Dream Home+ From US $590
         

New
House
WOW! Coastal Getaway: Hot Tub+FirePit+ Dream Home+
  • Air Conditioner
  • Parking
  • TV

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Chic One Bedroom Apartment In Portland's Arts District From US $286
         

10.0 (226 Reviews)
Apartment
Chic One Bedroom Apartment In Portland's Arts District
  • Air Conditioner
  • Parking
  • TV

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5 Star Back Cove Apartment with water view! From US $292
         

10.0 (152 Reviews)
House
5 Star Back Cove Apartment with water view!
  • Air Conditioner
  • Parking
  • TV

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Near Portland Trails: Walkable Apartment w/Deck From US $289
         

10.0 (50 Reviews)
House
Near Portland Trails: Walkable Apartment w/Deck
  • Air Conditioner
  • Parking
  • TV

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Historic Home in the West End. Private Parking. From US $244
         

10.0 (50 Reviews)
Apartment
Historic Home in the West End. Private Parking.
  • Air Conditioner
  • Parking
  • TV

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Bright & Sunny West End Apartment with Private Parking. From US $241
         

10.0 (46 Reviews)
Apartment
Bright & Sunny West End Apartment with Private Parking.
  • Air Conditioner
  • Parking
  • TV

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Charming Brownstone Downtown Free St|Perfect Getaway for 2 From US $236
         

10.0 (34 Reviews)
Apartment
Charming Brownstone Downtown Free St|Perfect Getaway for 2
  • Air Conditioner
  • TV
  • Security/Safety

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About Stroudwater Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bigpineresortcottages 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 with prices averaging $320 a night.

Bigpineresortcottages 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
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Stroudwater

★ Pro Tip: Bigpineresortcottages makes it easy to compare the best listings on Bigpineresortcottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bigpineresortcottages 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

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