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Gwynn Vacation Rentals

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50 rentals in Gwynn.
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Remote Island Rejuvenation + Enhanced Cleaning. WiFi. Pets Welcome!, vacation rental in Gwynn
Remote Island Rejuvenation + Enhanced Cleaning. WiFi. Pets Welcome!, vacation rental in Gwynn
Remote Island Rejuvenation + Enhanced Cleaning. WiFi. Pets Welcome!, vacation rental in Gwynn

Remote Island Rejuvenation + Enhanced Cleaning. WiFi. Pets Welcome!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Relax at the Mystic Seahorse Cottage on Gwynn's Island!, vacation rental in Gwynn
Relax at the Mystic Seahorse Cottage on Gwynn's Island!, vacation rental in Gwynn
Relax at the Mystic Seahorse Cottage on Gwynn's Island!, vacation rental in Gwynn

Relax at the Mystic Seahorse Cottage on Gwynn's Island!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline, vacation rental in Gwynn
PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline, vacation rental in Gwynn
PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline, vacation rental in Gwynn

PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Starlight Inlet, a quiet getaway on beautiful Gwynn's Island, VA., vacation rental in Gwynn
Starlight Inlet, a quiet getaway on beautiful Gwynn's Island, VA., vacation rental in Gwynn
Starlight Inlet, a quiet getaway on beautiful Gwynn's Island, VA., vacation rental in Gwynn

Starlight Inlet, a quiet getaway on beautiful Gwynn's Island, VA.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private Beachfront Home on Chesapeake Bay - Gwynn’s Island, vacation rental in Gwynn
Private Beachfront Home on Chesapeake Bay - Gwynn’s Island, vacation rental in Gwynn
Private Beachfront Home on Chesapeake Bay - Gwynn’s Island, vacation rental in Gwynn

Private Beachfront Home on Chesapeake Bay - Gwynn’s Island

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Craving small town comfort. Private riverfront for miles, beach, nature for all

Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Chesapeake Bay Boating, Fishing, and Private Beach, vacation rental in Gwynn
Chesapeake Bay Boating, Fishing, and Private Beach, vacation rental in Gwynn
Chesapeake Bay Boating, Fishing, and Private Beach, vacation rental in Gwynn

Chesapeake Bay Boating, Fishing, and Private Beach

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Experience the Chesapeake Bay At Gwynn's Island Cottage, vacation rental in Gwynn
Experience the Chesapeake Bay At Gwynn's Island Cottage, vacation rental in Gwynn
Experience the Chesapeake Bay At Gwynn's Island Cottage, vacation rental in Gwynn

Experience the Chesapeake Bay At Gwynn's Island Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Chesapeake Bay Waterfront: Kayaks, Fire Pit, Wifi, Bikes, Dog-friendly, vacation rental in Gwynn
Chesapeake Bay Waterfront: Kayaks, Fire Pit, Wifi, Bikes, Dog-friendly, vacation rental in Gwynn
Chesapeake Bay Waterfront: Kayaks, Fire Pit, Wifi, Bikes, Dog-friendly, vacation rental in Gwynn

Chesapeake Bay Waterfront: Kayaks, Fire Pit, Wifi, Bikes, Dog-friendly

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Chesapeake Bay Waterfront Cottage Pool, Pier, Kayaks, Wifi 2 Bd/2 Ba, Mini Golf, vacation rental in Gwynn
Chesapeake Bay Waterfront Cottage Pool, Pier, Kayaks, Wifi 2 Bd/2 Ba, Mini Golf, vacation rental in Gwynn
Chesapeake Bay Waterfront Cottage Pool, Pier, Kayaks, Wifi 2 Bd/2 Ba, Mini Golf, vacation rental in Gwynn

Chesapeake Bay Waterfront Cottage Pool, Pier, Kayaks, Wifi 2 Bd/2 Ba, Mini Golf

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private Waterfront Retreat on Winter Harbor, vacation rental in Gwynn
Private Waterfront Retreat on Winter Harbor, vacation rental in Gwynn
Private Waterfront Retreat on Winter Harbor, vacation rental in Gwynn

Private Waterfront Retreat on Winter Harbor

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Updated Waterfront Farmhouse on 3 Acres, vacation rental in Gwynn
Updated Waterfront Farmhouse on 3 Acres, vacation rental in Gwynn
Updated Waterfront Farmhouse on 3 Acres, vacation rental in Gwynn

Updated Waterfront Farmhouse on 3 Acres

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming Quiet Retreat on North River in Historic Gloucester, Virginia, vacation rental in Gwynn
Charming Quiet Retreat on North River in Historic Gloucester, Virginia, vacation rental in Gwynn
Charming Quiet Retreat on North River in Historic Gloucester, Virginia, vacation rental in Gwynn

Charming Quiet Retreat on North River in Historic Gloucester, Virginia

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Exquisite Riverfront Living! Newly renovated;  convenient to historic sites., vacation rental in Gwynn
Exquisite Riverfront Living! Newly renovated;  convenient to historic sites., vacation rental in Gwynn
Exquisite Riverfront Living! Newly renovated;  convenient to historic sites., vacation rental in Gwynn

Exquisite Riverfront Living! Newly renovated; convenient to historic sites.

Rental Home
5 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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MILLION $ VIEWS NO EXTRA CHARGE!  HOT TUB! POOL! BEACH!  RESORT-LIKE AMENITIES!, vacation rental in Gwynn
MILLION $ VIEWS NO EXTRA CHARGE!  HOT TUB! POOL! BEACH!  RESORT-LIKE AMENITIES!, vacation rental in Gwynn
MILLION $ VIEWS NO EXTRA CHARGE!  HOT TUB! POOL! BEACH!  RESORT-LIKE AMENITIES!, vacation rental in Gwynn

MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Vacation Getaway on Chesapeake Bay, vacation rental in Gwynn
Vacation Getaway on Chesapeake Bay, vacation rental in Gwynn
Vacation Getaway on Chesapeake Bay, vacation rental in Gwynn

Vacation Getaway on Chesapeake Bay

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beach House on Chesapeake Bay!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A 1763 Georgian Manor near Williamsburg and Virginia's Historic Triangle, vacation rental in Gwynn
A 1763 Georgian Manor near Williamsburg and Virginia's Historic Triangle, vacation rental in Gwynn
A 1763 Georgian Manor near Williamsburg and Virginia's Historic Triangle, vacation rental in Gwynn

A 1763 Georgian Manor near Williamsburg and Virginia's Historic Triangle

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Living Overlooking Private Pier-picturesque Views And Sunsets!, vacation rental in Gwynn
Waterfront Living Overlooking Private Pier-picturesque Views And Sunsets!, vacation rental in Gwynn
Waterfront Living Overlooking Private Pier-picturesque Views And Sunsets!, vacation rental in Gwynn

Waterfront Living Overlooking Private Pier-picturesque Views And Sunsets!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Fantastic waterfront home on Jackson Creek, vacation rental in Gwynn
Fantastic waterfront home on Jackson Creek, vacation rental in Gwynn
Fantastic waterfront home on Jackson Creek, vacation rental in Gwynn

Fantastic waterfront home on Jackson Creek

Rental Home
2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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The River House Getaway! Come Relax and Enjoy!, vacation rental in Gwynn
The River House Getaway! Come Relax and Enjoy!, vacation rental in Gwynn
The River House Getaway! Come Relax and Enjoy!, vacation rental in Gwynn

The River House Getaway! Come Relax and Enjoy!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Chesapeake Bay/Rappahannock River with Private Sandy Beach and, vacation rental in Gwynn
Chesapeake Bay/Rappahannock River with Private Sandy Beach and, vacation rental in Gwynn
Chesapeake Bay/Rappahannock River with Private Sandy Beach and, vacation rental in Gwynn

Chesapeake Bay/Rappahannock River with Private Sandy Beach and

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Chesapeake Bay Cottage, Private Pool, Pier and Kayaks, vacation rental in Gwynn
Chesapeake Bay Cottage, Private Pool, Pier and Kayaks, vacation rental in Gwynn
Chesapeake Bay Cottage, Private Pool, Pier and Kayaks, vacation rental in Gwynn

Chesapeake Bay Cottage, Private Pool, Pier and Kayaks

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Private, secluded waterfront cottage - pool and hot tub feet from the back door., vacation rental in Gwynn
Private, secluded waterfront cottage - pool and hot tub feet from the back door., vacation rental in Gwynn
Private, secluded waterfront cottage - pool and hot tub feet from the back door., vacation rental in Gwynn

Private, secluded waterfront cottage - pool and hot tub feet from the back door.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Teenie House in Deltaville, vacation rental in Gwynn
Teenie House in Deltaville, vacation rental in Gwynn
Teenie House in Deltaville, vacation rental in Gwynn

Teenie House in Deltaville

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Private Waterfront Retreat, vacation rental in Gwynn
Private Waterfront Retreat, vacation rental in Gwynn
Private Waterfront Retreat, vacation rental in Gwynn

Private Waterfront Retreat

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Historic Sea Captain’s Haven on Mobjack Bay

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront River Home- Chesapeake Bay, Deltaville, VA. Pier and Private Beach, vacation rental in Gwynn
Waterfront River Home- Chesapeake Bay, Deltaville, VA. Pier and Private Beach, vacation rental in Gwynn
Waterfront River Home- Chesapeake Bay, Deltaville, VA. Pier and Private Beach, vacation rental in Gwynn

Waterfront River Home- Chesapeake Bay, Deltaville, VA. Pier and Private Beach

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Teenie  Weenie  House in Deltaville, vacation rental in Gwynn
Teenie  Weenie  House in Deltaville, vacation rental in Gwynn
Teenie  Weenie  House in Deltaville, vacation rental in Gwynn

Teenie Weenie House in Deltaville

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Big Bay- A Private Beach front Home on the Chesapeake Bay, vacation rental in Gwynn
Big Bay- A Private Beach front Home on the Chesapeake Bay, vacation rental in Gwynn
Big Bay- A Private Beach front Home on the Chesapeake Bay, vacation rental in Gwynn

Big Bay- A Private Beach front Home on the Chesapeake Bay

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Chesapeake Bay Luxury Beachfront Retreat, vacation rental in Gwynn
Chesapeake Bay Luxury Beachfront Retreat, vacation rental in Gwynn
Chesapeake Bay Luxury Beachfront Retreat, vacation rental in Gwynn

Chesapeake Bay Luxury Beachfront Retreat

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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River House looking at the Chesapeake Bay, vacation rental in Gwynn
River House looking at the Chesapeake Bay, vacation rental in Gwynn
River House looking at the Chesapeake Bay, vacation rental in Gwynn

River House looking at the Chesapeake Bay

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Riverfront Cottage: Fire Pit, Kayaks & Paddle Boat, vacation rental in Gwynn
Riverfront Cottage: Fire Pit, Kayaks & Paddle Boat, vacation rental in Gwynn
Riverfront Cottage: Fire Pit, Kayaks & Paddle Boat, vacation rental in Gwynn

Riverfront Cottage: Fire Pit, Kayaks & Paddle Boat

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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NEW! Romantic Waterfront Abode with Patio & Dock!, vacation rental in Gwynn
NEW! Romantic Waterfront Abode with Patio & Dock!, vacation rental in Gwynn
NEW! Romantic Waterfront Abode with Patio & Dock!, vacation rental in Gwynn

NEW! Romantic Waterfront Abode with Patio & Dock!

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Welcome to 'The Happy Soul', vacation rental in Gwynn
Welcome to 'The Happy Soul', vacation rental in Gwynn
Welcome to 'The Happy Soul', vacation rental in Gwynn

Welcome to 'The Happy Soul'

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Love Shack - A Private Beachfront Home on the Chesapeake Bay, vacation rental in Gwynn
The Love Shack - A Private Beachfront Home on the Chesapeake Bay, vacation rental in Gwynn
The Love Shack - A Private Beachfront Home on the Chesapeake Bay, vacation rental in Gwynn

The Love Shack - A Private Beachfront Home on the Chesapeake Bay

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Waterfront Mobjack Bay Beach House in Gloucester!, vacation rental in Gwynn
Waterfront Mobjack Bay Beach House in Gloucester!, vacation rental in Gwynn
Waterfront Mobjack Bay Beach House in Gloucester!, vacation rental in Gwynn

Waterfront Mobjack Bay Beach House in Gloucester!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Chesapeake Bay Secluded Waterfront Log Cabin, vacation rental in Gwynn
Chesapeake Bay Secluded Waterfront Log Cabin, vacation rental in Gwynn
Chesapeake Bay Secluded Waterfront Log Cabin, vacation rental in Gwynn

Chesapeake Bay Secluded Waterfront Log Cabin

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Spacious home on the waterfront with kayaks, SUP's and fishing and more!, vacation rental in Gwynn
Spacious home on the waterfront with kayaks, SUP's and fishing and more!, vacation rental in Gwynn
Spacious home on the waterfront with kayaks, SUP's and fishing and more!, vacation rental in Gwynn

Spacious home on the waterfront with kayaks, SUP's and fishing and more!

Rental Home
5 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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My Pan-O-Sea-A  on the Chesapeake Bay. , vacation rental in Gwynn
My Pan-O-Sea-A  on the Chesapeake Bay. , vacation rental in Gwynn
My Pan-O-Sea-A  on the Chesapeake Bay. , vacation rental in Gwynn

My Pan-O-Sea-A on the Chesapeake Bay.

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Waterfront, Private Beach, Mid Century Style, vacation rental in Gwynn
Waterfront, Private Beach, Mid Century Style, vacation rental in Gwynn
Waterfront, Private Beach, Mid Century Style, vacation rental in Gwynn

Waterfront, Private Beach, Mid Century Style

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Rappahannock River waterfront property for rent with Pier &  Pool access, vacation rental in Gwynn
Rappahannock River waterfront property for rent with Pier &  Pool access, vacation rental in Gwynn
Rappahannock River waterfront property for rent with Pier &  Pool access, vacation rental in Gwynn

Rappahannock River waterfront property for rent with Pier & Pool access

Rental Home
3 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Oceanfront White Stone Cottage w/Private Beach!, vacation rental in Gwynn
Oceanfront White Stone Cottage w/Private Beach!, vacation rental in Gwynn
Oceanfront White Stone Cottage w/Private Beach!, vacation rental in Gwynn

Oceanfront White Stone Cottage w/Private Beach!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Mobjack Bay Cottage Overlooking East River & Mobjack Bay , vacation rental in Gwynn
Mobjack Bay Cottage Overlooking East River & Mobjack Bay , vacation rental in Gwynn
Mobjack Bay Cottage Overlooking East River & Mobjack Bay , vacation rental in Gwynn

Mobjack Bay Cottage Overlooking East River & Mobjack Bay

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Charming Guest Cottage on Jackson Creek w/kayaks and bikes available!, vacation rental in Gwynn
Charming Guest Cottage on Jackson Creek w/kayaks and bikes available!, vacation rental in Gwynn
Charming Guest Cottage on Jackson Creek w/kayaks and bikes available!, vacation rental in Gwynn

Charming Guest Cottage on Jackson Creek w/kayaks and bikes available!

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Home with Pier, 2bds/1ba, vacation rental in Gwynn
Waterfront Home with Pier, 2bds/1ba, vacation rental in Gwynn
Waterfront Home with Pier, 2bds/1ba, vacation rental in Gwynn

Waterfront Home with Pier, 2bds/1ba

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Windmill Point Beachfront 5 BR House on 2 acre lot, vacation rental in Gwynn
Windmill Point Beachfront 5 BR House on 2 acre lot, vacation rental in Gwynn
Windmill Point Beachfront 5 BR House on 2 acre lot, vacation rental in Gwynn

Windmill Point Beachfront 5 BR House on 2 acre lot

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Waterfront Modern Farmhouse, Privacy on 22 Acres, vacation rental in Gwynn
Waterfront Modern Farmhouse, Privacy on 22 Acres, vacation rental in Gwynn
Waterfront Modern Farmhouse, Privacy on 22 Acres, vacation rental in Gwynn

Waterfront Modern Farmhouse, Privacy on 22 Acres

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Get away to the Heart of Deltaville!, vacation rental in Gwynn
Get away to the Heart of Deltaville!, vacation rental in Gwynn
Get away to the Heart of Deltaville!, vacation rental in Gwynn

Get away to the Heart of Deltaville!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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