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Assawoman Vacation Rentals

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50 rentals in Assawoman.
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4 Bedrooms, flexible check in/out days, vacation rental in Assawoman
4 Bedrooms, flexible check in/out days, vacation rental in Assawoman
4 Bedrooms, flexible check in/out days, vacation rental in Assawoman

4 Bedrooms, flexible check in/out days

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Island Breeze  Cottage w/ screened porch. Water view! Quiet location!, vacation rental in Assawoman
Island Breeze  Cottage w/ screened porch. Water view! Quiet location!, vacation rental in Assawoman
Island Breeze  Cottage w/ screened porch. Water view! Quiet location!, vacation rental in Assawoman

Island Breeze Cottage w/ screened porch. Water view! Quiet location!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Whispering Pines - Your private getaway on Chincoteague Island, vacation rental in Assawoman
Whispering Pines - Your private getaway on Chincoteague Island, vacation rental in Assawoman
Whispering Pines - Your private getaway on Chincoteague Island, vacation rental in Assawoman

Whispering Pines - Your private getaway on Chincoteague Island

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Blue Chair Bay - Water Front - Townhouse, vacation rental in Assawoman
Blue Chair Bay - Water Front - Townhouse, vacation rental in Assawoman
Blue Chair Bay - Water Front - Townhouse, vacation rental in Assawoman

Blue Chair Bay - Water Front - Townhouse

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Perfect Chincoteague Home for your small family getaway, vacation rental in Assawoman
Perfect Chincoteague Home for your small family getaway, vacation rental in Assawoman
Perfect Chincoteague Home for your small family getaway, vacation rental in Assawoman

Perfect Chincoteague Home for your small family getaway

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Waterfront * Townhome * Dog-Friendly! * Pier, vacation rental in Assawoman
Waterfront * Townhome * Dog-Friendly! * Pier, vacation rental in Assawoman
Waterfront * Townhome * Dog-Friendly! * Pier, vacation rental in Assawoman

Waterfront * Townhome * Dog-Friendly! * Pier

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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'A Gem By The Sea' for your family., vacation rental in Assawoman
'A Gem By The Sea' for your family., vacation rental in Assawoman
'A Gem By The Sea' for your family., vacation rental in Assawoman

'A Gem By The Sea' for your family.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Blue Heron - A Breathtaking Eastern Shore Vacation Experience!, vacation rental in Assawoman
Blue Heron - A Breathtaking Eastern Shore Vacation Experience!, vacation rental in Assawoman
Blue Heron - A Breathtaking Eastern Shore Vacation Experience!, vacation rental in Assawoman

Blue Heron - A Breathtaking Eastern Shore Vacation Experience!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Pet Friendly * Beautiful Garden * Pool, vacation rental in Assawoman
Pet Friendly * Beautiful Garden * Pool, vacation rental in Assawoman
Pet Friendly * Beautiful Garden * Pool, vacation rental in Assawoman

Pet Friendly * Beautiful Garden * Pool

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beck's Corner is as cute as can be!, vacation rental in Assawoman
Beck's Corner is as cute as can be!, vacation rental in Assawoman
Beck's Corner is as cute as can be!, vacation rental in Assawoman

Beck's Corner is as cute as can be!

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Beautiful Park Setting & Water Views!, vacation rental in Assawoman
Beautiful Park Setting & Water Views!, vacation rental in Assawoman
Beautiful Park Setting & Water Views!, vacation rental in Assawoman

Beautiful Park Setting & Water Views!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Water Views * Newly Built * Great Floor Plan, vacation rental in Assawoman
Water Views * Newly Built * Great Floor Plan, vacation rental in Assawoman
Water Views * Newly Built * Great Floor Plan, vacation rental in Assawoman

Water Views * Newly Built * Great Floor Plan

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Pony Swim - Water Front - Water Access - Duplex, vacation rental in Assawoman
Pony Swim - Water Front - Water Access - Duplex, vacation rental in Assawoman
Pony Swim - Water Front - Water Access - Duplex, vacation rental in Assawoman

Pony Swim - Water Front - Water Access - Duplex

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Sleeps 8 * Waterfront * Pet Friendly, vacation rental in Assawoman
Sleeps 8 * Waterfront * Pet Friendly, vacation rental in Assawoman
Sleeps 8 * Waterfront * Pet Friendly, vacation rental in Assawoman

Sleeps 8 * Waterfront * Pet Friendly

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cute Beach Cottage * Pet Friendly, vacation rental in Assawoman
Cute Beach Cottage * Pet Friendly, vacation rental in Assawoman
Cute Beach Cottage * Pet Friendly, vacation rental in Assawoman

Cute Beach Cottage * Pet Friendly

Rental Home
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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West Haven - Water Front - Single Family Home, vacation rental in Assawoman
West Haven - Water Front - Single Family Home, vacation rental in Assawoman
West Haven - Water Front - Single Family Home, vacation rental in Assawoman

West Haven - Water Front - Single Family Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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This breathtaking waterfront home is the perfect place to make everlasting famil, vacation rental in Assawoman
This breathtaking waterfront home is the perfect place to make everlasting famil, vacation rental in Assawoman
This breathtaking waterfront home is the perfect place to make everlasting famil, vacation rental in Assawoman

This breathtaking waterfront home is the perfect place to make everlasting famil

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Miss Agnes - Water Front - Pet Friendly, vacation rental in Assawoman
Miss Agnes - Water Front - Pet Friendly, vacation rental in Assawoman
Miss Agnes - Water Front - Pet Friendly, vacation rental in Assawoman

Miss Agnes - Water Front - Pet Friendly

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Quaint Canalside Chincoteague Island Home w/ Pier!, vacation rental in Assawoman
Quaint Canalside Chincoteague Island Home w/ Pier!, vacation rental in Assawoman
Quaint Canalside Chincoteague Island Home w/ Pier!, vacation rental in Assawoman

Quaint Canalside Chincoteague Island Home w/ Pier!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful Updates * 3-level Decks * Amazing Sunsets * Downtown Location, vacation rental in Assawoman
Beautiful Updates * 3-level Decks * Amazing Sunsets * Downtown Location, vacation rental in Assawoman
Beautiful Updates * 3-level Decks * Amazing Sunsets * Downtown Location, vacation rental in Assawoman

Beautiful Updates * 3-level Decks * Amazing Sunsets * Downtown Location

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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YOUR RELAXING ISLAND SANCTUARY AWAITS!, vacation rental in Assawoman
YOUR RELAXING ISLAND SANCTUARY AWAITS!, vacation rental in Assawoman
YOUR RELAXING ISLAND SANCTUARY AWAITS!, vacation rental in Assawoman

YOUR RELAXING ISLAND SANCTUARY AWAITS!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Spacious, historic Chincoteague Is. vacation house, vacation rental in Assawoman
Spacious, historic Chincoteague Is. vacation house, vacation rental in Assawoman
Spacious, historic Chincoteague Is. vacation house, vacation rental in Assawoman

Spacious, historic Chincoteague Is. vacation house

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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We invite you to stay and leave feeling 'as fresh as a daisy', vacation rental in Assawoman
We invite you to stay and leave feeling 'as fresh as a daisy', vacation rental in Assawoman
We invite you to stay and leave feeling 'as fresh as a daisy', vacation rental in Assawoman

We invite you to stay and leave feeling 'as fresh as a daisy'

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sun Singer - Water View/Access- Pet Friendly - Townhouse, vacation rental in Assawoman
Sun Singer - Water View/Access- Pet Friendly - Townhouse, vacation rental in Assawoman
Sun Singer - Water View/Access- Pet Friendly - Townhouse, vacation rental in Assawoman

Sun Singer - Water View/Access- Pet Friendly - Townhouse

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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Chincoteague Townhome w/ Pony Views from Deck!, vacation rental in Assawoman
Chincoteague Townhome w/ Pony Views from Deck!, vacation rental in Assawoman
Chincoteague Townhome w/ Pony Views from Deck!, vacation rental in Assawoman

Chincoteague Townhome w/ Pony Views from Deck!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Spend time enjoying the land and Sea!, vacation rental in Assawoman
Spend time enjoying the land and Sea!, vacation rental in Assawoman
Spend time enjoying the land and Sea!, vacation rental in Assawoman

Spend time enjoying the land and Sea!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Sel de Mer - Single Family Home - Close to Town, vacation rental in Assawoman
Sel de Mer - Single Family Home - Close to Town, vacation rental in Assawoman
Sel de Mer - Single Family Home - Close to Town, vacation rental in Assawoman

Sel de Mer - Single Family Home - Close to Town

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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RELAXING AND INVITING!, vacation rental in Assawoman
RELAXING AND INVITING!, vacation rental in Assawoman
RELAXING AND INVITING!, vacation rental in Assawoman

RELAXING AND INVITING!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Secluded Home with ultimate privacy close to Chincoteague Island and NASA, vacation rental in Assawoman
Secluded Home with ultimate privacy close to Chincoteague Island and NASA, vacation rental in Assawoman
Secluded Home with ultimate privacy close to Chincoteague Island and NASA, vacation rental in Assawoman

Secluded Home with ultimate privacy close to Chincoteague Island and NASA

Rental Home
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
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Island Escape - Townhouse - Close to Town, vacation rental in Assawoman
Island Escape - Townhouse - Close to Town, vacation rental in Assawoman
Island Escape - Townhouse - Close to Town, vacation rental in Assawoman

Island Escape - Townhouse - Close to Town

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Miss Agnes - Water Front - Pet Friendly, vacation rental in Assawoman
Miss Agnes - Water Front - Pet Friendly, vacation rental in Assawoman
Miss Agnes - Water Front - Pet Friendly, vacation rental in Assawoman

Miss Agnes - Water Front - Pet Friendly

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Pony Swim - Water Front - Water Access - Duplex, vacation rental in Assawoman
Pony Swim - Water Front - Water Access - Duplex, vacation rental in Assawoman
Pony Swim - Water Front - Water Access - Duplex, vacation rental in Assawoman

Pony Swim - Water Front - Water Access - Duplex

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Summer Memories - Duplex - Close to Town, vacation rental in Assawoman
Summer Memories - Duplex - Close to Town, vacation rental in Assawoman
Summer Memories - Duplex - Close to Town, vacation rental in Assawoman

Summer Memories - Duplex - Close to Town

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Misty Manor - Pet Friendly - Single Family Home, vacation rental in Assawoman
Misty Manor - Pet Friendly - Single Family Home, vacation rental in Assawoman
Misty Manor - Pet Friendly - Single Family Home, vacation rental in Assawoman

Misty Manor - Pet Friendly - Single Family Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
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Island Retreat - Townhouse - Close to Town, vacation rental in Assawoman
Island Retreat - Townhouse - Close to Town, vacation rental in Assawoman
Island Retreat - Townhouse - Close to Town, vacation rental in Assawoman

Island Retreat - Townhouse - Close to Town

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
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Sea Gull Landing - Close to town - Duplex, vacation rental in Assawoman
Sea Gull Landing - Close to town - Duplex, vacation rental in Assawoman
Sea Gull Landing - Close to town - Duplex, vacation rental in Assawoman

Sea Gull Landing - Close to town - Duplex

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Seas The Day - Water Front - Water Access - Single Family Home, vacation rental in Assawoman
Seas The Day - Water Front - Water Access - Single Family Home, vacation rental in Assawoman
Seas The Day - Water Front - Water Access - Single Family Home, vacation rental in Assawoman

Seas The Day - Water Front - Water Access - Single Family Home

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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West Haven - Water Front - Single Family Home, vacation rental in Assawoman
West Haven - Water Front - Single Family Home, vacation rental in Assawoman
West Haven - Water Front - Single Family Home, vacation rental in Assawoman

West Haven - Water Front - Single Family Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Sun Singer - Water View/Access- Pet Friendly - Townhouse, vacation rental in Assawoman
Sun Singer - Water View/Access- Pet Friendly - Townhouse, vacation rental in Assawoman
Sun Singer - Water View/Access- Pet Friendly - Townhouse, vacation rental in Assawoman

Sun Singer - Water View/Access- Pet Friendly - Townhouse

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Seas The Day - Water Front - Water Access - Single Family Home, vacation rental in Assawoman
Seas The Day - Water Front - Water Access - Single Family Home, vacation rental in Assawoman
Seas The Day - Water Front - Water Access - Single Family Home, vacation rental in Assawoman

Seas The Day - Water Front - Water Access - Single Family Home

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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YOUR RELAXING ISLAND VACATION AWAITS!, vacation rental in Assawoman
YOUR RELAXING ISLAND VACATION AWAITS!, vacation rental in Assawoman
YOUR RELAXING ISLAND VACATION AWAITS!, vacation rental in Assawoman

YOUR RELAXING ISLAND VACATION AWAITS!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Glamp in style at Pony Pines Farm, vacation rental in Assawoman
Glamp in style at Pony Pines Farm, vacation rental in Assawoman
Glamp in style at Pony Pines Farm, vacation rental in Assawoman

Glamp in style at Pony Pines Farm

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Saltwater Cowboy - Single Family Home - Close to Town, vacation rental in Assawoman
Saltwater Cowboy - Single Family Home - Close to Town, vacation rental in Assawoman
Saltwater Cowboy - Single Family Home - Close to Town, vacation rental in Assawoman

Saltwater Cowboy - Single Family Home - Close to Town

Rental Home
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Pony Pines of Chincoteague Waterfront Cottage, vacation rental in Assawoman
Pony Pines of Chincoteague Waterfront Cottage, vacation rental in Assawoman
Pony Pines of Chincoteague Waterfront Cottage, vacation rental in Assawoman

Pony Pines of Chincoteague Waterfront Cottage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Shore Bird - Single Family Studio Cottage -, vacation rental in Assawoman
Shore Bird - Single Family Studio Cottage -, vacation rental in Assawoman
Shore Bird - Single Family Studio Cottage -, vacation rental in Assawoman

Shore Bird - Single Family Studio Cottage -

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cypress Cottage - Waterview - Close to town, vacation rental in Assawoman
Cypress Cottage - Waterview - Close to town, vacation rental in Assawoman
Cypress Cottage - Waterview - Close to town, vacation rental in Assawoman

Cypress Cottage - Waterview - Close to town

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
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Sel de Mer - Single Family Home - Close to Town, vacation rental in Assawoman
Sel de Mer - Single Family Home - Close to Town, vacation rental in Assawoman
Sel de Mer - Single Family Home - Close to Town, vacation rental in Assawoman

Sel de Mer - Single Family Home - Close to Town

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Mae's Landing - Pet Friendly - Close to town, vacation rental in Assawoman
Mae's Landing - Pet Friendly - Close to town, vacation rental in Assawoman
Mae's Landing - Pet Friendly - Close to town, vacation rental in Assawoman

Mae's Landing - Pet Friendly - Close to town

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
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Sea Ridge - Pet Friendly - Single Family Home, vacation rental in Assawoman
Sea Ridge - Pet Friendly - Single Family Home, vacation rental in Assawoman
Sea Ridge - Pet Friendly - Single Family Home, vacation rental in Assawoman

Sea Ridge - Pet Friendly - Single Family Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
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Sunset View - Water Front - Water Access - Single Family Home, vacation rental in Assawoman
Sunset View - Water Front - Water Access - Single Family Home, vacation rental in Assawoman
Sunset View - Water Front - Water Access - Single Family Home, vacation rental in Assawoman

Sunset View - Water Front - Water Access - Single Family Home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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