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Westbrook Holiday Rentals

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50 rentals in Westbrook.
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Highland House, holiday rental in Westbrook

Highland House

7 bedrooms
3 bathrooms
Sleeps 23
Match: Sleeps
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Fox Crossing - Riverside, walk to restaurants, breweries, holiday rental in Westbrook

Fox Crossing - Riverside, walk to restaurants, breweries

5 bedrooms
4 bathrooms
Sleeps 20
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Nature with in-town living that feels a world away, holiday rental in Westbrook

Nature with in-town living that feels a world away

3 bedrooms
3 bathrooms
Sleeps 6
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Chic One Bedroom Apartment In Portland's Arts District, holiday rental in Westbrook

Chic One Bedroom Apartment In Portland's Arts District

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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“Percival” Penthouse Suite: Breathtaking Views, Cupola, Walk to Restaurants, holiday rental in Westbrook

“Percival” Penthouse Suite: Breathtaking Views, Cupola, Walk to Restaurants

2 bedrooms
2 bathrooms
Sleeps 4
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Fully Furnished Executive/Garden Apartment In Falmouth, Maine, holiday rental in Westbrook

Fully Furnished Executive/Garden Apartment In Falmouth, Maine

1 bedroom
1 bathroom
Sleeps 3
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Glorious getaway on Portland's Eastern Promenade., holiday rental in Westbrook

Glorious getaway on Portland's Eastern Promenade.

2 bedrooms
1 bathroom
Sleeps 6
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Historic West End Neighborhood, holiday rental in Westbrook

Historic West End Neighborhood

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Charming 2-bedroom steps from the Eastern Promenade, holiday rental in Westbrook

Charming 2-bedroom steps from the Eastern Promenade

2 bedrooms
1 bathroom
Sleeps 5
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Simonson Lakeside 4 Bedrooms, holiday rental in Westbrook

Simonson Lakeside 4 Bedrooms

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quaint Maine Farmhouse Near Portland, holiday rental in Westbrook

Quaint Maine Farmhouse Near Portland

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Falmouth Furnished 3 Bedroom 2 Bath Loft Close to Portland, holiday rental in Westbrook

Beautiful Falmouth Furnished 3 Bedroom 2 Bath Loft Close to Portland

3 bedrooms
2 bathrooms
Sleeps 6
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Simonson Lakeside on Highland Lake, holiday rental in Westbrook

Simonson Lakeside on Highland Lake

2 bedrooms
2 bathrooms
Sleeps 4
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Great Captains House Portland, holiday rental in Westbrook

Great Captains House Portland

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Getaway In The City, holiday rental in Westbrook

Cozy Getaway In The City

1 bedroom
1 bathroom
Sleeps 3
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Private Apt in Scarborough Near Portland and Maine Beaches, holiday rental in Westbrook

Private Apt in Scarborough Near Portland and Maine Beaches

1 bedroom
1 bathroom
Sleeps 4
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3BR home: East End neighborhood: walk to ocean or downtown, local eateries, holiday rental in Westbrook

3BR home: East End neighborhood: walk to ocean or downtown, local eateries

3 bedrooms
1 bathroom
Sleeps 10
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Adorable Portland getaway on the Eastern Promenade, holiday rental in Westbrook

Adorable Portland getaway on the Eastern Promenade

1 bedroom
1 bathroom
Sleeps 4
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The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!, holiday rental in Westbrook

The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!

1 bedroom
1 bathroom
Sleeps 3
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Modern Apartment Two Blocks from Willard Beach in South Portland, holiday rental in Westbrook

Modern Apartment Two Blocks from Willard Beach in South Portland

1 bedroom
1 bathroom
Sleeps 4
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Sleek Condo w/ a Private Patio - Less than Two Blocks from the Beach/Park, holiday rental in Westbrook

Sleek Condo w/ a Private Patio - Less than Two Blocks from the Beach/Park

2 bedrooms
1 bathroom
Sleeps 6
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Art Filled East End Home a short walk to waterfront, restaurants and shops, holiday rental in Westbrook

Art Filled East End Home a short walk to waterfront, restaurants and shops

3 bedrooms
3 bathrooms
Sleeps 6
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Stunning Waterfront House with Hot Tub, holiday rental in Westbrook

Stunning Waterfront House with Hot Tub

6 bedrooms
3 bathrooms
Sleeps 14
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Swim spa under the starry night with pool/hot tub/sauna, holiday rental in Westbrook

Swim spa under the starry night with pool/hot tub/sauna

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Elegant condo w/ gas fireplace - walk to Portland's best restaurants & Old Port!, holiday rental in Westbrook

Elegant condo w/ gas fireplace - walk to Portland's best restaurants & Old Port!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood, holiday rental in Westbrook

2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood

2 bedrooms
1 bathroom
Sleeps 4
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Fresh East End Apartment Walkable to Downtown Portland, holiday rental in Westbrook

Fresh East End Apartment Walkable to Downtown Portland

1 bedroom
1 bathroom
Sleeps 4
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Spacious 5 Bedroom, 2 Full Baths, Walkable Neighborhood, holiday rental in Westbrook

Spacious 5 Bedroom, 2 Full Baths, Walkable Neighborhood

5 bedrooms
2 bathrooms
Sleeps 20
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Be Near Willard Beach in a Wonderful Residential Neighborhood, holiday rental in Westbrook

Be Near Willard Beach in a Wonderful Residential Neighborhood

2 bedrooms
1 bathroom
Sleeps 4
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Sleek & Newly-Renovated Third-Floor Condo w/ Amazing Water Views - Walk to Bay!, holiday rental in Westbrook

Sleek & Newly-Renovated Third-Floor Condo w/ Amazing Water Views - Walk to Bay!

2 bedrooms
1 bathroom
Sleeps 4
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Polished, Modern Condo w/ a Balcony - Walk to Eastern Promenade & Casco Bay!, holiday rental in Westbrook

Polished, Modern Condo w/ a Balcony - Walk to Eastern Promenade & Casco Bay!

2 bedrooms
1 bathroom
Sleeps 4
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Classic Maine waterfront cottage on pristine Highland Lake Windham/Falmouth, holiday rental in Westbrook

Classic Maine waterfront cottage on pristine Highland Lake Windham/Falmouth

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Back Cove Charmer Close to Everything, holiday rental in Westbrook

Back Cove Charmer Close to Everything

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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7 Minutes to the Old Port!  Steps to the Back Cove / Ocean!  Entire Home, holiday rental in Westbrook

7 Minutes to the Old Port! Steps to the Back Cove / Ocean! Entire Home

6 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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Historic Island Cottage, 5BR, holiday rental in Westbrook

Historic Island Cottage, 5BR

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lovely Cape Elizabeth Family Home 5 miles to Portland! 3,700 sqft custom built!!, holiday rental in Westbrook

Lovely Cape Elizabeth Family Home 5 miles to Portland! 3,700 sqft custom built!!

5 bedrooms
3 bathrooms
Sleeps 8
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Cozy, Pet Friendly, Home In A Quiet Family Oriented, Beach Neighborhood, holiday rental in Westbrook

Cozy, Pet Friendly, Home In A Quiet Family Oriented, Beach Neighborhood

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious duplex w/ furnished deck & patio! Great for families & close to beach!, holiday rental in Westbrook

Spacious duplex w/ furnished deck & patio! Great for families & close to beach!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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BRAND NEW luxury penthouse condo w/ water views right in the heart of Old Port!, holiday rental in Westbrook

BRAND NEW luxury penthouse condo w/ water views right in the heart of Old Port!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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1st Floor Private Entrance Condo.  Walk to Restaurants and Parks!, holiday rental in Westbrook

1st Floor Private Entrance Condo. Walk to Restaurants and Parks!

4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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Andy's Retreat - Heated outdoor pool, Hot Spring jacuzzi, central AC, BBQ, holiday rental in Westbrook

Andy's Retreat - Heated outdoor pool, Hot Spring jacuzzi, central AC, BBQ

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront villa,  Coastal Southern Maine, holiday rental in Westbrook

Waterfront villa, Coastal Southern Maine

4 bedrooms
6 bathrooms
Sleeps 10
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K2 Lake Paradise, holiday rental in Westbrook

K2 Lake Paradise

2 bedrooms
1 bathroom
Sleeps 7
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Casco Bay Sunrise Vista, holiday rental in Westbrook

Casco Bay Sunrise Vista

1 bedroom
1 bathroom
Sleeps 3
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The perfect refinement of vintage seduction, holiday rental in Westbrook

The perfect refinement of vintage seduction

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning - modern 2 bedroom Victorian mansion pad, holiday rental in Westbrook

Stunning - modern 2 bedroom Victorian mansion pad

2 bedrooms
2 bathrooms
Sleeps 4
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Ultra cool new modern flat, holiday rental in Westbrook

Ultra cool new modern flat

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Victorian architecture dipped in refined modernity, holiday rental in Westbrook

Victorian architecture dipped in refined modernity

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newer South Portland Cottage, 10-Min to Downtown, 30-Day Rentals, holiday rental in Westbrook

Newer South Portland Cottage, 10-Min to Downtown, 30-Day Rentals

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Swim spa under the starry night with pool/hot tub/sauna, holiday rental in Westbrook

Swim spa under the starry night with pool/hot tub/sauna

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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