We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Gwynn Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
50 rentals in Gwynn.
Sort by:
Tripadvisor Sort
Remote Island Rejuvenation + Enhanced Cleaning. WiFi. Pets Welcome!, holiday rental in Gwynn

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline, holiday rental in Gwynn

PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Relax at the Mystic Seahorse Cottage on Gwynn's Island!, holiday rental in Gwynn

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Private Beachfront Home on Chesapeake Bay - Gwynn’s Island, holiday rental in Gwynn

Private Beachfront Home on Chesapeake Bay - Gwynn’s Island

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Starlight Inlet, a quiet getaway on beautiful Gwynn's Island, VA., holiday rental in Gwynn

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Craving small town comfort. Private riverfront for miles, beach, nature for all, holiday rental in Gwynn

Craving small town comfort. Private riverfront for miles, beach, nature for all

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
'Pop Castle' Historic Gem on the Rappahannock River, holiday rental in Gwynn

'Pop Castle' Historic Gem on the Rappahannock River

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Chesapeake Bay Boating, Fishing, and Private Beach, holiday rental in Gwynn

Chesapeake Bay Boating, Fishing, and Private Beach

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Experience the Chesapeake Bay At Gwynn's Island Cottage, holiday rental in Gwynn

Experience the Chesapeake Bay At Gwynn's Island Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Chesapeake Bay Waterfront Cottage Pool, Pier, Kayaks, Wifi 2 Bd/2 Ba, Mini Golf, holiday rental in Gwynn

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Gwynn rentals sent straight to your email!
Updated Waterfront Farmhouse on 3 Acres, holiday rental in Gwynn

Updated Waterfront Farmhouse on 3 Acres

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg, holiday rental in Gwynn

Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Exquisite Riverfront Living! Newly renovated;  convenient to historic sites., holiday rental in Gwynn

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

5 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Vacation Getaway on Chesapeake Bay, holiday rental in Gwynn

Vacation Getaway on Chesapeake Bay

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Chesapeake Bay Waterfront: Kayaks, Fire Pit, Wifi, Bikes, Dog-friendly, holiday rental in Gwynn

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

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
A 1763 Georgian Manor near Williamsburg and Virginia's Historic Triangle, holiday rental in Gwynn

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

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Charming Quiet Retreat on North River in Historic Gloucester, Virginia, holiday rental in Gwynn

Charming Quiet Retreat on North River in Historic Gloucester, Virginia

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beach House on Chesapeake Bay!, holiday rental in Gwynn

Beach House on Chesapeake Bay!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Private Waterfront Retreat on Winter Harbor, holiday rental in Gwynn

Private Waterfront Retreat on Winter Harbor

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**, holiday rental in Gwynn

A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Welcome to 'A Shore Thing!'  Waterfront Apartment for Two, holiday rental in Gwynn

Welcome to 'A Shore Thing!' Waterfront Apartment for Two

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Fantastic waterfront home on Jackson Creek, holiday rental in Gwynn

Fantastic waterfront home on Jackson Creek

2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Chesapeake Bay/Rappahannock River with Private Sandy Beach and, holiday rental in Gwynn

Chesapeake Bay/Rappahannock River with Private Sandy Beach and

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Chesapeake Bay Cottage, Private Pool, Pier and Kayaks, holiday rental in Gwynn

Chesapeake Bay Cottage, Private Pool, Pier and Kayaks

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Historic Sea Captain’s Haven on Mobjack Bay, holiday rental in Gwynn

Historic Sea Captain’s Haven on Mobjack Bay

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Private, secluded waterfront cottage - pool and hot tub feet from the back door., holiday rental in Gwynn

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Private Waterfront Retreat, holiday rental in Gwynn

Private Waterfront Retreat

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Modern Family Beachfront Cottage with Endless Bay Views, holiday rental in Gwynn

Modern Family Beachfront Cottage with Endless Bay Views

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Waterview & Water Access, Luxurious Retreat, holiday rental in Gwynn

Waterview & Water Access, Luxurious Retreat

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Big Bay- A Private Beach front Home on the Chesapeake Bay, holiday rental in Gwynn

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Enjoy Sunsets On The Creek In Your Own Private Paradise., holiday rental in Gwynn

Enjoy Sunsets On The Creek In Your Own Private Paradise.

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Waterfront River Home- Chesapeake Bay, Deltaville, VA. Pier and Private Beach, holiday rental in Gwynn

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

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Waterfront Kayak and Nature Lovers Dream Mathews County Farmhouse, holiday rental in Gwynn

Waterfront Kayak and Nature Lovers Dream Mathews County Farmhouse

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Virginia's Northern Neck   Spectacular Waterfront Home, holiday rental in Gwynn

Virginia's Northern Neck Spectacular Waterfront Home

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
'Bee Haven' Cottage Retreat Near Colonial Williamsburg, holiday rental in Gwynn

'Bee Haven' Cottage Retreat Near Colonial Williamsburg

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
The Love Shack - A Private Beachfront Home on the Chesapeake Bay, holiday rental in Gwynn

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Chesapeake Bay Secluded Waterfront Log Cabin, holiday rental in Gwynn

Chesapeake Bay Secluded Waterfront Log Cabin

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
My Pan-O-Sea-A  on the Chesapeake Bay., holiday rental in Gwynn

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Pop Castle- Historic Gem on the Rappahannock River, holiday rental in Gwynn

Pop Castle- Historic Gem on the Rappahannock River

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Crane's Nest - a charming fully renovated farmhouse, holiday rental in Gwynn

The Crane's Nest - a charming fully renovated farmhouse

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Waterfront, Private Beach, Mid Century Style, holiday rental in Gwynn

Waterfront, Private Beach, Mid Century Style

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Mobjack Bay Cottage Overlooking East River & Mobjack Bay, holiday rental in Gwynn

Mobjack Bay Cottage Overlooking East River & Mobjack Bay

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beautiful Private Room  with en-suite in Charming  newly renovated Farmhouse, holiday rental in Gwynn

Beautiful Private Room with en-suite in Charming newly renovated Farmhouse

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
NEW! Romantic Waterfront Abode with Patio & Dock!, holiday rental in Gwynn

NEW! Romantic Waterfront Abode with Patio & Dock!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Waterfront Home with Pier, 2bds/1ba, holiday rental in Gwynn

Waterfront Home with Pier, 2bds/1ba

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Oceanfront White Stone Cottage w/ Private Beach!, holiday rental in Gwynn

Oceanfront White Stone Cottage w/ Private Beach!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Waterfront Mobjack Bay Beach House in Gloucester!, holiday rental in Gwynn

Waterfront Mobjack Bay Beach House in Gloucester!

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Riverfront Cottage: Fire Pit & Kayaks, holiday rental in Gwynn

Riverfront Cottage: Fire Pit & Kayaks

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Waterfront Modern Farmhouse on 22 Private Acres, holiday rental in Gwynn

Waterfront Modern Farmhouse on 22 Private Acres

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Luxe Waterfront Home: Kayak, Canoe, Grill + More!, holiday rental in Gwynn

Luxe Waterfront Home: Kayak, Canoe, Grill + More!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PreviousNext
1
Frequently Asked Questions about Gwynn