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Westerly Holiday Rentals

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49 rentals in Westerly.
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Welcome to the Wanderer!, holiday rental in Westerly

Welcome to the Wanderer!

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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2 Blocks from Beach!!! Welcome to Harmony Cottage in Idyllic Westerly, RI, holiday rental in Westerly

2 Blocks from Beach!!! Welcome to Harmony Cottage in Idyllic Westerly, RI

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Ocean Front Cottage with Private Beach on Watch Hill end of Westerly, holiday rental in Westerly

Ocean Front Cottage with Private Beach on Watch Hill end of Westerly

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Classic Cozy Cottage in Watch Hill, holiday rental in Westerly

Classic Cozy Cottage in Watch Hill

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Quaint Westerly Cottage Walking Distance To The Beach, holiday rental in Westerly

Quaint Westerly Cottage Walking Distance To The Beach

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Downtown Living-- great location!  Beach pass., holiday rental in Westerly

Downtown Living-- great location! Beach pass.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Amazing Ocean Front 2 Story Home, Steps Away From The Water, holiday rental in Westerly

Amazing Ocean Front 2 Story Home, Steps Away From The Water

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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'The Boulders' - A Watch Hill Five Bedroom House, holiday rental in Westerly

'The Boulders' - A Watch Hill Five Bedroom House

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Thanksgiving near your Southeastern RI family- sleeps 7, holiday rental in Westerly

Thanksgiving near your Southeastern RI family- sleeps 7

3 bedrooms
2 bathrooms
Sleeps 7
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Beach Goers Paradise, holiday rental in Westerly

Beach Goers Paradise

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Brand New Beach House 500 ft from the beach!  Available June 8-29th 2019, holiday rental in Westerly

Brand New Beach House 500 ft from the beach! Available June 8-29th 2019

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Bright, Spacious 6 Bedroom, 3 Blocks from access to beaches, private, amenities, holiday rental in Westerly

Bright, Spacious 6 Bedroom, 3 Blocks from access to beaches, private, amenities

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Quintessential New England Home on Private Beach, holiday rental in Westerly

Quintessential New England Home on Private Beach

4 bedrooms
4 bathrooms
Sleeps 10
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We Call it Ponder!!!, holiday rental in Westerly

We Call it Ponder!!!

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tranquil & Privately Located Beach Cottage Escape!, holiday rental in Westerly

Tranquil & Privately Located Beach Cottage Escape!

2 bedrooms
1 bathroom
Sleeps 6
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Steps from East Beach- 3 beds option 4 beds option discounts apply for 7+ nights, holiday rental in Westerly

Steps from East Beach- 3 beds option 4 beds option discounts apply for 7+ nights

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming, Cottage-Style Home Near Everything!, holiday rental in Westerly

Charming, Cottage-Style Home Near Everything!

4 bedrooms
3 bathrooms
Sleeps 6
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1 Mile To Beach, 2BR, 1 BA, sleeps 6, holiday rental in Westerly

1 Mile To Beach, 2BR, 1 BA, sleeps 6

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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JUST FOOTSTEPS FROM THE WATER! AVAILABLE MAY, JUNE, & SEPT, holiday rental in Westerly

JUST FOOTSTEPS FROM THE WATER! AVAILABLE MAY, JUNE, & SEPT

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Watch Hill  4BR/3BA with Backyard Deck & Pool Just Steps From Beach, holiday rental in Westerly

Beautiful Watch Hill 4BR/3BA with Backyard Deck & Pool Just Steps From Beach

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Misquamicut Waterfront Beach House, holiday rental in Westerly

Misquamicut Waterfront Beach House

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Rent on a quiet street steps from the beach in the heart of historic Watch Hill, holiday rental in Westerly

Rent on a quiet street steps from the beach in the heart of historic Watch Hill

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cozy summer cottage, short walk to beach and historic Watch Hill village, holiday rental in Westerly

Cozy summer cottage, short walk to beach and historic Watch Hill village

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A Stunning Studio filled with light and steps from the Beach, holiday rental in Westerly

A Stunning Studio filled with light and steps from the Beach

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Check out the surf at Fenway Beach from the patio, holiday rental in Westerly

Check out the surf at Fenway Beach from the patio

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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5 minute walk to the beach and restaurants and provides peace and tranquility., holiday rental in Westerly

5 minute walk to the beach and restaurants and provides peace and tranquility.

3 bedrooms
3 bathrooms
Sleeps 6
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3BR Vacation House w/Private Beach across the street, holiday rental in Westerly

3BR Vacation House w/Private Beach across the street

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sunny, bright house with water views in private neighborhood, holiday rental in Westerly

Sunny, bright house with water views in private neighborhood

5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Pine Lodge Condos, holiday rental in Westerly

Pine Lodge Condos

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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WALK TO BEACH! Misquamicut cottage Weekly rentals, holiday rental in Westerly

WALK TO BEACH! Misquamicut cottage Weekly rentals

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront Cottage Westerly, holiday rental in Westerly

Waterfront Cottage Westerly

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cute Beach House with two minute walk to Private Beach, holiday rental in Westerly

Cute Beach House with two minute walk to Private Beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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W2133 Shore House, holiday rental in Westerly

W2133 Shore House

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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NEW! Beach Home w/ Deck + Views: 1 Block to Ocean!, holiday rental in Westerly

NEW! Beach Home w/ Deck + Views: 1 Block to Ocean!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Villa Rosa, holiday rental in Westerly

Villa Rosa

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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W463 Baker - Four Bedroom House, holiday rental in Westerly

W463 Baker - Four Bedroom House

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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W2108 The Grey, holiday rental in Westerly

W2108 The Grey

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Villa Rosa A, holiday rental in Westerly

Villa Rosa A

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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W943 DeWalt - Five Bedroom House, holiday rental in Westerly

W943 DeWalt - Five Bedroom House

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Pawcatuck Riverfront Home w/Yard - Mins to Beach!, holiday rental in Westerly

Pawcatuck Riverfront Home w/Yard - Mins to Beach!

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Villa Rosa 2, holiday rental in Westerly

Villa Rosa 2

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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3 bedroom all year round home, holiday rental in Westerly

3 bedroom all year round home

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Bright Family-Friendly Pond-Side Retreat with Priv, holiday rental in Westerly

Bright Family-Friendly Pond-Side Retreat with Priv

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Weekapaug Home w/ Heated Pool Through Columbus Weekend!, holiday rental in Westerly

Beautiful Weekapaug Home w/ Heated Pool Through Columbus Weekend!

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Walk to East Beach Watch Hill, holiday rental in Westerly

Walk to East Beach Watch Hill

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3BR Ocean Views in Weekapaug, holiday rental in Westerly

3BR Ocean Views in Weekapaug

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to the Windward, holiday rental in Westerly

Welcome to the Windward

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beachfront/Oceanfront Timeshare Unit available JULY 18-25,2020 from $385 to $285, holiday rental in Westerly

Beachfront/Oceanfront Timeshare Unit available JULY 18-25,2020 from $385 to $285

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Quaint Coastal Cottage with Patio - Walk to Beach!, holiday rental in Westerly

Quaint Coastal Cottage with Patio - Walk to Beach!

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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