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Chester Vacation Rentals

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50 rentals in Chester.
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Delightful self contained cottage in the Charming Village of Chester by the sea, vacation rental in Chester
Delightful self contained cottage in the Charming Village of Chester by the sea, vacation rental in Chester
Delightful self contained cottage in the Charming Village of Chester by the sea, vacation rental in Chester

Delightful self contained cottage in the Charming Village of Chester by the sea

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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CHESTER VILLAGE EXQUISITE DESIGNER CLASSIC, 5 Bedrooms, 2 Baths, vacation rental in Chester
CHESTER VILLAGE EXQUISITE DESIGNER CLASSIC, 5 Bedrooms, 2 Baths, vacation rental in Chester
CHESTER VILLAGE EXQUISITE DESIGNER CLASSIC, 5 Bedrooms, 2 Baths, vacation rental in Chester

CHESTER VILLAGE EXQUISITE DESIGNER CLASSIC, 5 Bedrooms, 2 Baths

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Superb Oceanfront with Boathouse, vacation rental in Chester
Superb Oceanfront with Boathouse, vacation rental in Chester
Superb Oceanfront with Boathouse, vacation rental in Chester

Superb Oceanfront with Boathouse

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Family Cottage in the Village of Chester NS - 5 Bedrooms, vacation rental in Chester
Family Cottage in the Village of Chester NS - 5 Bedrooms, vacation rental in Chester
Family Cottage in the Village of Chester NS - 5 Bedrooms, vacation rental in Chester

Family Cottage in the Village of Chester NS - 5 Bedrooms

Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Stoneybrook House - historic property on 1.7 acres of land, vacation rental in Chester
Stoneybrook House - historic property on 1.7 acres of land, vacation rental in Chester
Stoneybrook House - historic property on 1.7 acres of land, vacation rental in Chester

Stoneybrook House - historic property on 1.7 acres of land

Rental Home
6 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Breath taking Ocean Harbour Front 3 Bedroom 2 Bath, vacation rental in Chester
Breath taking Ocean Harbour Front 3 Bedroom 2 Bath, vacation rental in Chester
Breath taking Ocean Harbour Front 3 Bedroom 2 Bath, vacation rental in Chester

Breath taking Ocean Harbour Front 3 Bedroom 2 Bath

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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5 bedroom quiet and spacious retreat, vacation rental in Chester
5 bedroom quiet and spacious retreat, vacation rental in Chester
5 bedroom quiet and spacious retreat, vacation rental in Chester

5 bedroom quiet and spacious retreat

Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Quiet, Peaceful, Private Country Home on Large Area of Land, vacation rental in Chester
Quiet, Peaceful, Private Country Home on Large Area of Land, vacation rental in Chester
Quiet, Peaceful, Private Country Home on Large Area of Land, vacation rental in Chester

Quiet, Peaceful, Private Country Home on Large Area of Land

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Carriage House, vacation rental in Chester
Carriage House, vacation rental in Chester
Carriage House, vacation rental in Chester

Carriage House

Rental Home
2 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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Enjoy the good life at Casa Blanca Cottage, vacation rental in Chester
Enjoy the good life at Casa Blanca Cottage, vacation rental in Chester
Enjoy the good life at Casa Blanca Cottage, vacation rental in Chester

Enjoy the good life at Casa Blanca Cottage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Seascape,Art Deco cottage, vacation rental in Chester
Seascape,Art Deco cottage, vacation rental in Chester
Seascape,Art Deco cottage, vacation rental in Chester

Seascape,Art Deco cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Chester Trail Suite, vacation rental in Chester
Chester Trail Suite, vacation rental in Chester
Chester Trail Suite, vacation rental in Chester

Chester Trail Suite

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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SANDY COVE COTTAGE / CHESTER / oceanfront / private beach and wharf / kayak, vacation rental in Chester
SANDY COVE COTTAGE / CHESTER / oceanfront / private beach and wharf / kayak, vacation rental in Chester
SANDY COVE COTTAGE / CHESTER / oceanfront / private beach and wharf / kayak, vacation rental in Chester

SANDY COVE COTTAGE / CHESTER / oceanfront / private beach and wharf / kayak

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Ahoy... Relax & Enjoy this Private Oceanfront Cottage with Hot Tub, vacation rental in Chester
Ahoy... Relax & Enjoy this Private Oceanfront Cottage with Hot Tub, vacation rental in Chester
Ahoy... Relax & Enjoy this Private Oceanfront Cottage with Hot Tub, vacation rental in Chester

Ahoy... Relax & Enjoy this Private Oceanfront Cottage with Hot Tub

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Serenity Cottage borders the beautiful Coveside Stable in Chester., vacation rental in Chester
Serenity Cottage borders the beautiful Coveside Stable in Chester., vacation rental in Chester
Serenity Cottage borders the beautiful Coveside Stable in Chester., vacation rental in Chester

Serenity Cottage borders the beautiful Coveside Stable in Chester.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Oceanfront Air Conditioned Boat House - One of a Kind! With Water Access., vacation rental in Chester
Oceanfront Air Conditioned Boat House - One of a Kind! With Water Access., vacation rental in Chester
Oceanfront Air Conditioned Boat House - One of a Kind! With Water Access., vacation rental in Chester

Oceanfront Air Conditioned Boat House - One of a Kind! With Water Access.

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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On the Beautiful South Shore Near Chester and Hubbards, Ns, vacation rental in Chester
On the Beautiful South Shore Near Chester and Hubbards, Ns, vacation rental in Chester
On the Beautiful South Shore Near Chester and Hubbards, Ns, vacation rental in Chester

On the Beautiful South Shore Near Chester and Hubbards, Ns

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cooperage Cottage - Peaceful & Family Friendly, Oceanfront, vacation rental in Chester
Cooperage Cottage - Peaceful & Family Friendly, Oceanfront, vacation rental in Chester
Cooperage Cottage - Peaceful & Family Friendly, Oceanfront, vacation rental in Chester

Cooperage Cottage - Peaceful & Family Friendly, Oceanfront

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The White Cape on the Cove - A year round oceanside retreat, vacation rental in Chester
The White Cape on the Cove - A year round oceanside retreat, vacation rental in Chester
The White Cape on the Cove - A year round oceanside retreat, vacation rental in Chester

The White Cape on the Cove - A year round oceanside retreat

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Somerset Cottage - Only a Stroll to the Beach, vacation rental in Chester
Somerset Cottage - Only a Stroll to the Beach, vacation rental in Chester
Somerset Cottage - Only a Stroll to the Beach, vacation rental in Chester

Somerset Cottage - Only a Stroll to the Beach

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Oceanfront Elegant Home with Games Room On Picturesque Big Tancook Island, vacation rental in Chester
Oceanfront Elegant Home with Games Room On Picturesque Big Tancook Island, vacation rental in Chester
Oceanfront Elegant Home with Games Room On Picturesque Big Tancook Island, vacation rental in Chester

Oceanfront Elegant Home with Games Room On Picturesque Big Tancook Island

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Compass Cottage at Deep Cove, vacation rental in Chester
Compass Cottage at Deep Cove, vacation rental in Chester
Compass Cottage at Deep Cove, vacation rental in Chester

Compass Cottage at Deep Cove

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanfront 5 Bedroom Home on Mahone Bay, vacation rental in Chester
Oceanfront 5 Bedroom Home on Mahone Bay, vacation rental in Chester
Oceanfront 5 Bedroom Home on Mahone Bay, vacation rental in Chester

Oceanfront 5 Bedroom Home on Mahone Bay

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Sandy Cove Exclusive, vacation rental in Chester
Sandy Cove Exclusive, vacation rental in Chester
Sandy Cove Exclusive, vacation rental in Chester

Sandy Cove Exclusive

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay, vacation rental in Chester
Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay, vacation rental in Chester
Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay, vacation rental in Chester

Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Modern Oceanview Vacation Living In Deep Cove, vacation rental in Chester
Modern Oceanview Vacation Living In Deep Cove, vacation rental in Chester
Modern Oceanview Vacation Living In Deep Cove, vacation rental in Chester

Modern Oceanview Vacation Living In Deep Cove

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Custom Built Home On The Scenic Waterfront Facing The Picturesque MarriottsCove, vacation rental in Chester
Custom Built Home On The Scenic Waterfront Facing The Picturesque MarriottsCove, vacation rental in Chester
Custom Built Home On The Scenic Waterfront Facing The Picturesque MarriottsCove, vacation rental in Chester

Custom Built Home On The Scenic Waterfront Facing The Picturesque MarriottsCove

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Second Wind Cottage - ocean front chalet near Mahone Bay & Lunenburg Nova Scotia, vacation rental in Chester
Second Wind Cottage - ocean front chalet near Mahone Bay & Lunenburg Nova Scotia, vacation rental in Chester
Second Wind Cottage - ocean front chalet near Mahone Bay & Lunenburg Nova Scotia, vacation rental in Chester

Second Wind Cottage - ocean front chalet near Mahone Bay & Lunenburg Nova Scotia

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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4 Bed (Sleeps 8) persons Vacation Rental with cottage, private dock and beach., vacation rental in Chester
4 Bed (Sleeps 8) persons Vacation Rental with cottage, private dock and beach., vacation rental in Chester
4 Bed (Sleeps 8) persons Vacation Rental with cottage, private dock and beach., vacation rental in Chester

4 Bed (Sleeps 8) persons Vacation Rental with cottage, private dock and beach.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Calm and Relaxing sunrise Oceanview of Oak Island. 2 "Master" bedrooms., vacation rental in Chester
Calm and Relaxing sunrise Oceanview of Oak Island. 2 "Master" bedrooms., vacation rental in Chester
Calm and Relaxing sunrise Oceanview of Oak Island. 2 "Master" bedrooms., vacation rental in Chester

Calm and Relaxing sunrise Oceanview of Oak Island. 2 "Master" bedrooms.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Coffee With A View Of  Deep Cove, vacation rental in Chester
Coffee With A View Of  Deep Cove, vacation rental in Chester
Coffee With A View Of  Deep Cove, vacation rental in Chester

Coffee With A View Of Deep Cove

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A Sailors Paradise - Stevens Cove Guest Quarters, vacation rental in Chester
A Sailors Paradise - Stevens Cove Guest Quarters, vacation rental in Chester
A Sailors Paradise - Stevens Cove Guest Quarters, vacation rental in Chester

A Sailors Paradise - Stevens Cove Guest Quarters

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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White Cape on the Cove - Year round ocean retreat!, vacation rental in Chester
White Cape on the Cove - Year round ocean retreat!, vacation rental in Chester
White Cape on the Cove - Year round ocean retreat!, vacation rental in Chester

White Cape on the Cove - Year round ocean retreat!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Bright Spacious Family Suite in Historic Farmhouse on Sunny Acreage, vacation rental in Chester
Bright Spacious Family Suite in Historic Farmhouse on Sunny Acreage, vacation rental in Chester
Bright Spacious Family Suite in Historic Farmhouse on Sunny Acreage, vacation rental in Chester

Bright Spacious Family Suite in Historic Farmhouse on Sunny Acreage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Gorgeous Oceanfront Estate with Heated Pool, vacation rental in Chester
Gorgeous Oceanfront Estate with Heated Pool, vacation rental in Chester
Gorgeous Oceanfront Estate with Heated Pool, vacation rental in Chester

Gorgeous Oceanfront Estate with Heated Pool

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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The Boathouse at Strum Island, vacation rental in Chester
The Boathouse at Strum Island, vacation rental in Chester
The Boathouse at Strum Island, vacation rental in Chester

The Boathouse at Strum Island

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Stylish Riverside Country Queen Room in Historic Farmhouse, vacation rental in Chester
Stylish Riverside Country Queen Room in Historic Farmhouse, vacation rental in Chester
Stylish Riverside Country Queen Room in Historic Farmhouse, vacation rental in Chester

Stylish Riverside Country Queen Room in Historic Farmhouse

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Executive Ocean Front Estate with View of Waters of Mahone Bay, vacation rental in Chester
Executive Ocean Front Estate with View of Waters of Mahone Bay, vacation rental in Chester
Executive Ocean Front Estate with View of Waters of Mahone Bay, vacation rental in Chester

Executive Ocean Front Estate with View of Waters of Mahone Bay

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Beautiful Waterfront Home In Chester Basin On The Shores Of Mahone Bay -, vacation rental in Chester
Beautiful Waterfront Home In Chester Basin On The Shores Of Mahone Bay -, vacation rental in Chester
Beautiful Waterfront Home In Chester Basin On The Shores Of Mahone Bay -, vacation rental in Chester

Beautiful Waterfront Home In Chester Basin On The Shores Of Mahone Bay -

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Riverside Country Retreat near Mahone Bay, Lunenburg and Oak Island, vacation rental in Chester
Riverside Country Retreat near Mahone Bay, Lunenburg and Oak Island, vacation rental in Chester
Riverside Country Retreat near Mahone Bay, Lunenburg and Oak Island, vacation rental in Chester

Riverside Country Retreat near Mahone Bay, Lunenburg and Oak Island

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Lodge at Strum Island - A Private Island Paradise with a Club Ambiance, vacation rental in Chester
The Lodge at Strum Island - A Private Island Paradise with a Club Ambiance, vacation rental in Chester
The Lodge at Strum Island - A Private Island Paradise with a Club Ambiance, vacation rental in Chester

The Lodge at Strum Island - A Private Island Paradise with a Club Ambiance

Rental Home
6 bedrooms
7 bathrooms
Sleeps 6
Match: Sleeps
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OCEANFRONT LONG COVE NOVA SCOTIA, NEAR MAHONE BAY, vacation rental in Chester
OCEANFRONT LONG COVE NOVA SCOTIA, NEAR MAHONE BAY, vacation rental in Chester
OCEANFRONT LONG COVE NOVA SCOTIA, NEAR MAHONE BAY, vacation rental in Chester

OCEANFRONT LONG COVE NOVA SCOTIA, NEAR MAHONE BAY

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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On the Cove Seaside Cottage - Blandford, Nova Scotia, Canada, vacation rental in Chester
On the Cove Seaside Cottage - Blandford, Nova Scotia, Canada, vacation rental in Chester
On the Cove Seaside Cottage - Blandford, Nova Scotia, Canada, vacation rental in Chester

On the Cove Seaside Cottage - Blandford, Nova Scotia, Canada

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Well-appointed Queen Room in Riverside Historic Farmhouse Getaway, vacation rental in Chester
Well-appointed Queen Room in Riverside Historic Farmhouse Getaway, vacation rental in Chester
Well-appointed Queen Room in Riverside Historic Farmhouse Getaway, vacation rental in Chester

Well-appointed Queen Room in Riverside Historic Farmhouse Getaway

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Vintage 4 person camper with all amenities, vacation rental in Chester
Vintage 4 person camper with all amenities, vacation rental in Chester
Vintage 4 person camper with all amenities, vacation rental in Chester

Vintage 4 person camper with all amenities

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Breathtaking Oceanfront Chateau, vacation rental in Chester
Breathtaking Oceanfront Chateau, vacation rental in Chester
Breathtaking Oceanfront Chateau, vacation rental in Chester

Breathtaking Oceanfront Chateau

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Chester Oceanfront Luxury Villa with Outstanding Decor, vacation rental in Chester
Chester Oceanfront Luxury Villa with Outstanding Decor, vacation rental in Chester
Chester Oceanfront Luxury Villa with Outstanding Decor, vacation rental in Chester

Chester Oceanfront Luxury Villa with Outstanding Decor

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Oceanfront cozy comfortable cottage!, vacation rental in Chester
Oceanfront cozy comfortable cottage!, vacation rental in Chester
Oceanfront cozy comfortable cottage!, vacation rental in Chester

Oceanfront cozy comfortable cottage!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Seaside Oasis, vacation rental in Chester
Seaside Oasis, vacation rental in Chester
Seaside Oasis, vacation rental in Chester

Seaside Oasis

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Astounding Oak Island Log Chateau, vacation rental in Chester
Astounding Oak Island Log Chateau, vacation rental in Chester
Astounding Oak Island Log Chateau, vacation rental in Chester

Astounding Oak Island Log Chateau

Rental Home
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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