Windham Vacation Rentals

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The Pilot & Plover Lakeside Retreat
The Pilot & Plover Lakeside Retreat
The Pilot & Plover Lakeside Retreat
The Pilot & Plover Lakeside Retreat
The Pilot & Plover Lakeside Retreat
The Pilot & Plover Lakeside Retreat
The Pilot & Plover Lakeside Retreat
The Pilot & Plover Lakeside Retreat
The Pilot & Plover Lakeside Retreat
The Pilot & Plover Lakeside Retreat
The Pilot & Plover Lakeside Retreat
The Pilot & Plover Lakeside Retreat
The Pilot & Plover Lakeside Retreat
The Pilot & Plover Lakeside Retreat
The Pilot & Plover Lakeside Retreat
5 Bedrooms
2 Bathrooms
$401 - $1300 / night (excl. fees & taxes)
Cozy Loft - Mountain Views & Sebago Lake Access
Cozy Loft - Mountain Views & Sebago Lake Access
Cozy Loft - Mountain Views & Sebago Lake Access
Cozy Loft - Mountain Views & Sebago Lake Access
Cozy Loft - Mountain Views & Sebago Lake Access
Cozy Loft - Mountain Views & Sebago Lake Access
Cozy Loft - Mountain Views & Sebago Lake Access
Cozy Loft - Mountain Views & Sebago Lake Access
Cozy Loft - Mountain Views & Sebago Lake Access
Cozy Loft - Mountain Views & Sebago Lake Access
Cozy Loft - Mountain Views & Sebago Lake Access
Cozy Loft - Mountain Views & Sebago Lake Access
Cozy Loft - Mountain Views & Sebago Lake Access
Cozy Loft - Mountain Views & Sebago Lake Access
Cozy Loft - Mountain Views & Sebago Lake Access
1 Bedroom
1 Bathroom
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4 reviews
$80 - $150 / night (excl. fees & taxes)
Modern Guest House + garden patio on Munjoy Hill
Modern Guest House + garden patio on Munjoy Hill
Modern Guest House + garden patio on Munjoy Hill
Modern Guest House + garden patio on Munjoy Hill
Modern Guest House + garden patio on Munjoy Hill
Modern Guest House + garden patio on Munjoy Hill
Modern Guest House + garden patio on Munjoy Hill
Modern Guest House + garden patio on Munjoy Hill
Modern Guest House + garden patio on Munjoy Hill
Modern Guest House + garden patio on Munjoy Hill
Modern Guest House + garden patio on Munjoy Hill
Modern Guest House + garden patio on Munjoy Hill
Modern Guest House + garden patio on Munjoy Hill
Modern Guest House + garden patio on Munjoy Hill
Modern Guest House + garden patio on Munjoy Hill
2 Bedrooms
1½ Bathrooms
4.98IconIconIconIconIcon
55 reviews
$167 - $723 / night (excl. fees & taxes)
Modern Loft in the Old Port
Modern Loft in the Old Port
Modern Loft in the Old Port
Modern Loft in the Old Port
Modern Loft in the Old Port
2 Bedrooms
1 Bathroom
$900 / night (excl. fees & taxes)
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Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
Luxury Penthouse Steps from Downtown Portland
2 Bedrooms
1 Bathroom
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6 reviews
$349 - $1149 / night (excl. fees & taxes)
Sweet Home Near Food & Old Port
Sweet Home Near Food & Old Port
Sweet Home Near Food & Old Port
Sweet Home Near Food & Old Port
Sweet Home Near Food & Old Port
Sweet Home Near Food & Old Port
Sweet Home Near Food & Old Port
Sweet Home Near Food & Old Port
Sweet Home Near Food & Old Port
Sweet Home Near Food & Old Port
Sweet Home Near Food & Old Port
Sweet Home Near Food & Old Port
Sweet Home Near Food & Old Port
Sweet Home Near Food & Old Port
Sweet Home Near Food & Old Port
2 Bedrooms
1½ Bathrooms
$315 - $450 / night (excl. fees & taxes)
West End Room Near Top Food & Old Port Attractions
West End Room Near Top Food & Old Port Attractions
West End Room Near Top Food & Old Port Attractions
West End Room Near Top Food & Old Port Attractions
West End Room Near Top Food & Old Port Attractions
West End Room Near Top Food & Old Port Attractions
West End Room Near Top Food & Old Port Attractions
West End Room Near Top Food & Old Port Attractions
West End Room Near Top Food & Old Port Attractions
West End Room Near Top Food & Old Port Attractions
West End Room Near Top Food & Old Port Attractions
West End Room Near Top Food & Old Port Attractions
West End Room Near Top Food & Old Port Attractions
West End Room Near Top Food & Old Port Attractions
West End Room Near Top Food & Old Port Attractions
1 Bedroom
1 Bathroom
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6 reviews
$90 - $170 / night (excl. fees & taxes)
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Tranquil 3B Residence: Near Downtown Portland
Tranquil 3B Residence: Near Downtown Portland
Tranquil 3B Residence: Near Downtown Portland
Tranquil 3B Residence: Near Downtown Portland
Tranquil 3B Residence: Near Downtown Portland
Tranquil 3B Residence: Near Downtown Portland
Tranquil 3B Residence: Near Downtown Portland
Tranquil 3B Residence: Near Downtown Portland
Tranquil 3B Residence: Near Downtown Portland
Tranquil 3B Residence: Near Downtown Portland
Tranquil 3B Residence: Near Downtown Portland
Tranquil 3B Residence: Near Downtown Portland
Tranquil 3B Residence: Near Downtown Portland
Tranquil 3B Residence: Near Downtown Portland
Tranquil 3B Residence: Near Downtown Portland
3 Bedrooms
2 Bathrooms
$86 - $199 / night (excl. fees & taxes)
Cute and cozy lake view cottage
Cute and cozy lake view cottage
Cute and cozy lake view cottage
Cute and cozy lake view cottage
Cute and cozy lake view cottage
Cute and cozy lake view cottage
Cute and cozy lake view cottage
Cute and cozy lake view cottage
Cute and cozy lake view cottage
Cute and cozy lake view cottage
Cute and cozy lake view cottage
Cute and cozy lake view cottage
Cute and cozy lake view cottage
Cute and cozy lake view cottage
Cute and cozy lake view cottage
2 Bedrooms
1 Bathroom
$200 - $250 / night (excl. fees & taxes)
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Point Sebago Haven: Beach, Arcade & More Awaits
Point Sebago Haven: Beach, Arcade & More Awaits
Point Sebago Haven: Beach, Arcade & More Awaits
Point Sebago Haven: Beach, Arcade & More Awaits
Point Sebago Haven: Beach, Arcade & More Awaits
Point Sebago Haven: Beach, Arcade & More Awaits
Point Sebago Haven: Beach, Arcade & More Awaits
Point Sebago Haven: Beach, Arcade & More Awaits
Point Sebago Haven: Beach, Arcade & More Awaits
Point Sebago Haven: Beach, Arcade & More Awaits
Point Sebago Haven: Beach, Arcade & More Awaits
Point Sebago Haven: Beach, Arcade & More Awaits
Point Sebago Haven: Beach, Arcade & More Awaits
Point Sebago Haven: Beach, Arcade & More Awaits
Point Sebago Haven: Beach, Arcade & More Awaits
2 Bedrooms
1 Bathroom
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2 reviews
$89 - $449 / night (excl. fees & taxes)
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Pine Point Getaway: Beach House with Fire Pit
Pine Point Getaway: Beach House with Fire Pit
Pine Point Getaway: Beach House with Fire Pit
Pine Point Getaway: Beach House with Fire Pit
Pine Point Getaway: Beach House with Fire Pit
Pine Point Getaway: Beach House with Fire Pit
Pine Point Getaway: Beach House with Fire Pit
Pine Point Getaway: Beach House with Fire Pit
Pine Point Getaway: Beach House with Fire Pit
Pine Point Getaway: Beach House with Fire Pit
Pine Point Getaway: Beach House with Fire Pit
Pine Point Getaway: Beach House with Fire Pit
Pine Point Getaway: Beach House with Fire Pit
Pine Point Getaway: Beach House with Fire Pit
Pine Point Getaway: Beach House with Fire Pit
2 Bedrooms
2 Bathrooms
4.67IconIconIconIconIcon
6 reviews
$108 - $610 / night (excl. fees & taxes)
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Boho Beach Escape: Top-Floor Condo
Boho Beach Escape: Top-Floor Condo
Boho Beach Escape: Top-Floor Condo
Boho Beach Escape: Top-Floor Condo
Boho Beach Escape: Top-Floor Condo
Boho Beach Escape: Top-Floor Condo
Boho Beach Escape: Top-Floor Condo
Boho Beach Escape: Top-Floor Condo
Boho Beach Escape: Top-Floor Condo
Boho Beach Escape: Top-Floor Condo
Boho Beach Escape: Top-Floor Condo
Boho Beach Escape: Top-Floor Condo
Boho Beach Escape: Top-Floor Condo
Boho Beach Escape: Top-Floor Condo
Boho Beach Escape: Top-Floor Condo
2 Bedrooms
1 Bathroom
$109 - $599 / night (excl. fees & taxes)
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Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
Steps to sand ☀ 2story+Deck ☀ Stellar Ocean Views!
3 Bedrooms
1½ Bathrooms
4.88IconIconIconIconIcon
8 reviews
$173 - $529 / night (excl. fees & taxes)
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Beach Getaway: 5BR Home Near Attractions
Beach Getaway: 5BR Home Near Attractions
Beach Getaway: 5BR Home Near Attractions
Beach Getaway: 5BR Home Near Attractions
Beach Getaway: 5BR Home Near Attractions
Beach Getaway: 5BR Home Near Attractions
Beach Getaway: 5BR Home Near Attractions
Beach Getaway: 5BR Home Near Attractions
Beach Getaway: 5BR Home Near Attractions
Beach Getaway: 5BR Home Near Attractions
Beach Getaway: 5BR Home Near Attractions
Beach Getaway: 5BR Home Near Attractions
Beach Getaway: 5BR Home Near Attractions
Beach Getaway: 5BR Home Near Attractions
Beach Getaway: 5BR Home Near Attractions
5 Bedrooms
2 Bathrooms
$180 - $1150 / night (excl. fees & taxes)
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Oceanfront Escape with Pool, Beach, and Comfort
Oceanfront Escape with Pool, Beach, and Comfort
Oceanfront Escape with Pool, Beach, and Comfort
Oceanfront Escape with Pool, Beach, and Comfort
Oceanfront Escape with Pool, Beach, and Comfort
Oceanfront Escape with Pool, Beach, and Comfort
Oceanfront Escape with Pool, Beach, and Comfort
Oceanfront Escape with Pool, Beach, and Comfort
Oceanfront Escape with Pool, Beach, and Comfort
Oceanfront Escape with Pool, Beach, and Comfort
Oceanfront Escape with Pool, Beach, and Comfort
Oceanfront Escape with Pool, Beach, and Comfort
Oceanfront Escape with Pool, Beach, and Comfort
Oceanfront Escape with Pool, Beach, and Comfort
Oceanfront Escape with Pool, Beach, and Comfort
2 Bedrooms
2 Bathrooms
$99 - $519 / night (excl. fees & taxes)
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Downtown Penthouse with Ocean Views & Rooftop Deck
Downtown Penthouse with Ocean Views & Rooftop Deck
Downtown Penthouse with Ocean Views & Rooftop Deck
Downtown Penthouse with Ocean Views & Rooftop Deck
Downtown Penthouse with Ocean Views & Rooftop Deck
Downtown Penthouse with Ocean Views & Rooftop Deck
Downtown Penthouse with Ocean Views & Rooftop Deck
Downtown Penthouse with Ocean Views & Rooftop Deck
Downtown Penthouse with Ocean Views & Rooftop Deck
Downtown Penthouse with Ocean Views & Rooftop Deck
Downtown Penthouse with Ocean Views & Rooftop Deck
Downtown Penthouse with Ocean Views & Rooftop Deck
Downtown Penthouse with Ocean Views & Rooftop Deck
Downtown Penthouse with Ocean Views & Rooftop Deck
Downtown Penthouse with Ocean Views & Rooftop Deck
4 Bedrooms
2 Bathrooms
$225 - $599 / night (excl. fees & taxes)
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Old Orchard Beach Retreat | 2BD Cottage
Old Orchard Beach Retreat | 2BD Cottage
Old Orchard Beach Retreat | 2BD Cottage
Old Orchard Beach Retreat | 2BD Cottage
Old Orchard Beach Retreat | 2BD Cottage
Old Orchard Beach Retreat | 2BD Cottage
Old Orchard Beach Retreat | 2BD Cottage
Old Orchard Beach Retreat | 2BD Cottage
Old Orchard Beach Retreat | 2BD Cottage
Old Orchard Beach Retreat | 2BD Cottage
Old Orchard Beach Retreat | 2BD Cottage
Old Orchard Beach Retreat | 2BD Cottage
Old Orchard Beach Retreat | 2BD Cottage
Old Orchard Beach Retreat | 2BD Cottage
Old Orchard Beach Retreat | 2BD Cottage
2 Bedrooms
1 Bathroom
$85 - $339 / night (excl. fees & taxes)
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Cozy Cottage Stay w/ Pool & Parking
Cozy Cottage Stay w/ Pool & Parking
Cozy Cottage Stay w/ Pool & Parking
Cozy Cottage Stay w/ Pool & Parking
Cozy Cottage Stay w/ Pool & Parking
Cozy Cottage Stay w/ Pool & Parking
Cozy Cottage Stay w/ Pool & Parking
Cozy Cottage Stay w/ Pool & Parking
Cozy Cottage Stay w/ Pool & Parking
Cozy Cottage Stay w/ Pool & Parking
Cozy Cottage Stay w/ Pool & Parking
Cozy Cottage Stay w/ Pool & Parking
Cozy Cottage Stay w/ Pool & Parking
Cozy Cottage Stay w/ Pool & Parking
Cozy Cottage Stay w/ Pool & Parking
1 Bedroom
1 Bathroom
$100 - $349 / night (excl. fees & taxes)
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Cozy Single Bed Room w Pool & Parking
Cozy Single Bed Room w Pool & Parking
Cozy Single Bed Room w Pool & Parking
Cozy Single Bed Room w Pool & Parking
Cozy Single Bed Room w Pool & Parking
Cozy Single Bed Room w Pool & Parking
Cozy Single Bed Room w Pool & Parking
Cozy Single Bed Room w Pool & Parking
Cozy Single Bed Room w Pool & Parking
Cozy Single Bed Room w Pool & Parking
Cozy Single Bed Room w Pool & Parking
Cozy Single Bed Room w Pool & Parking
Cozy Single Bed Room w Pool & Parking
Cozy Single Bed Room w Pool & Parking
Cozy Single Bed Room w Pool & Parking
1 Bedroom
1 Bathroom
$74 - $279 / night (excl. fees & taxes)
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Family-Friendly Cottage w/ Pool & Parking
Family-Friendly Cottage w/ Pool & Parking
Family-Friendly Cottage w/ Pool & Parking
Family-Friendly Cottage w/ Pool & Parking
Family-Friendly Cottage w/ Pool & Parking
Family-Friendly Cottage w/ Pool & Parking
Family-Friendly Cottage w/ Pool & Parking
Family-Friendly Cottage w/ Pool & Parking
Family-Friendly Cottage w/ Pool & Parking
Family-Friendly Cottage w/ Pool & Parking
Family-Friendly Cottage w/ Pool & Parking
Family-Friendly Cottage w/ Pool & Parking
Family-Friendly Cottage w/ Pool & Parking
Family-Friendly Cottage w/ Pool & Parking
Family-Friendly Cottage w/ Pool & Parking
1 Bedroom
1 Bathroom
$110 - $349 / night (excl. fees & taxes)
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