Holiday houses in Gwynn

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Top-rated holiday rentals in Gwynn

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home in Grimstead

4.85 out of 5 average rating, 262 reviews

Gwynns Island Waterfront Getaway

Great cottage on the water with a fantastic view of the bay and best sunset on the east coast. Sliding glass doors make it feel like your on the water when your sitting on the couch or in the kitchen. You can crab, fish, kayak, grill out and swim right off the back deck. Very peaceful and relaxing. The newly renovated island restuarant is a mile away with a bar and bascically anything you would want to eat. My father left us the house, we use all the proceeds from Airbnb to make improvements.

29 Nov – 6 Dec

$378 NZD per night

Guest favourite

Apartment in North

4.97 out of 5 average rating, 190 reviews

Little Cove Cottage, Mathews

Little Cove Cottage: a charming studio in Mathews County with private entrance. Mathews is a rural town with several beautiful beaches close by and many areas to access the water. This apartment offers a small water view of the North River, with a pier and boat ramp just 400 yards away. Bring your Kayaks or use ours. . We are just minutes away from the Mobjack and Chesapeake Bays. Mathews is home to great restaurants with fresh seafood. We also have a wonderful farmer's market. Come enjoy!

29 Sep – 6 Oct

$210 NZD per night

Guest favourite

Home in Cobbs Creek

4.99 out of 5 average rating, 133 reviews

Blue Heron WaterSide

Blue Heron Waterside awaits you...Private Hot Tub, Pool, Waterfront and Pier- Kayaks included! This retreat is set up with you in mind for a special get away.Relax.Enjoy being together plus space to have quiet time. Sunroom, spacious deck, private Pool, Hot tub and Pier create a waterfront living experience. Grab a book, go for a swim or lounge by the pool. Explore the water with a variety of Kayaks plus a Stand Up Paddle Board.Great location to fish and crab from the pier. Are you ready?

26 Jan – 2 Feb

$721 NZD per night

Guest favourite

Home in Deltaville

4.95 out of 5 average rating, 130 reviews

The Oyster House

PETS MUST BE PRE-APPROVED ($45 pet fee)! If a quiet country setting is your relaxation, this is your place. Surrounded by open fields that attract deer, turkey, osprey, ground hogs, this is natures haven. Outdoor seating around a permanent firepit or covered backporch with bar top overlooking wildlife. Renovated 2019. Yet, just seconds from downtown Deltaville. House accommodates wheelchairs. Bonus Event Room (The Spat) for 4 people available for extra cost. Ask re: price/availability.

27 Nov – 4 Dec

$259 NZD per night

Guest favourite

Cottage in Gloucester

4.97 out of 5 average rating, 194 reviews

"Bee Haven" Cottage Retreat

Curious about what makes Gloucester so wonderful? Live like a local at "Bee Haven Retreat" and find out for yourself at our newly renovated 2 bedroom cottage. Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our street is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

17–24 Sep

$252 NZD per night

Superhost

Home in Mathews

4.85 out of 5 average rating, 114 reviews

Piper’s Landing: Relaxing beach house near the Bay

This home is ideal for those who enjoy nature, as it is close to Bethel Beach Park and Nature Preserve and has easy kayak access via a public dock within 2000 feet. The home has two double beds, one king bed, and two additional pull-outs. Our perfect getaway includes two kayaks, two adult bicycles, and fishing poles for you to use. You are only 2 Minutes from Bethel Beach Nature Preserve 15 minutes from Mathews 60 Minutes to Virginia Beach 60 Minutes to Williamsburg/Jamestown

30 Sep – 7 Oct

$297 NZD per night

Guest favourite

Guesthouse in White Stone

5.0 out of 5 average rating, 187 reviews

Waterfront Guesthouse II on the Rappahannock

The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

13–20 Feb

$391 NZD per night

Guest favourite

Farm stay in Cardinal

4.95 out of 5 average rating, 106 reviews

Wtrfrnt aptmnt w/pool/dock on private farm

Come enjoy all the outdoors has on offer at this secluded, waterfront estate. The spacious studio apartment is fully equipped for comfort. 12 acres of waterfront grounds to enjoy including great outdoor seating, fabulous bayside salt water pool. Fish, canoe and kayak right off the farms private dock. Grill and fire pit. Just 10 mins from the charming villages of Mathews and Gloucesters farm to table amenities. Great local food, music, history and shopping right on the bay!

11–18 Jul

$332 NZD per night

Guest favourite

Guesthouse in Saluda

4.93 out of 5 average rating, 467 reviews

Wooded Cabin retreat on fresh water pond

If your looking for a quiet place in a wooded setting, this is it. Cabin has view of private 7.5 acre pond, deck and walking trail to the scenic Dragon Run, with canoe portage. You are welcome to bring your canoe/kayak. Bird watchers, wildflower enthusiasts will enjoy what the Dragon Run has to offer. If shopping or history is your interest, this cabin is only 45 min away from Williamsburg, and will give you a place to relax. This is a pet friendly cabin.

5–12 Sep

$182 NZD per night

Guest favourite

Home in Cobbs Creek

4.9 out of 5 average rating, 116 reviews

Millionaire $ Views No Xtra Charge! Hot Tub! POOL!

"Now this is the life!" "A little piece of paradise!" "Livin the Dream!" "It doesn't get any better than this!" Just a few thoughts that may cross your mind when you come for a stay at The Cottage at Misti Cove. While the name may be simple, don't let that fool you, for so are the best things in life! Getting a taste of the simple life doesn't mean you have to sacrifice amenities. Here, you'll enjoy resort-like amenities without resort crowds.

11–18 Jan

$459 NZD per night

Guest favourite

Cottage in Gwynn

4.96 out of 5 average rating, 200 reviews

Mystic Seahorse Cottage & game room

Welcome to our quiet corner of Gwynn’s Island! It may be cool outside but you can relax inside with a movie, hang out in the heated game room, warm up around the firepit, or take a walk to the beach. The cottage is clean and stocked with everything you need for a relaxing visit. Drive 10 minutes to Mathews for great restaurants and shopping, or an hour to Yorktown, Jamestown and Williamsburg. Come relax and enjoy some Island Time with us!

28 Aug – 4 Sep

$331 NZD per night

Guest favourite

Cottage in White Stone

4.91 out of 5 average rating, 297 reviews

The Moore Cottage

The Moore Cottage is a rustic-chic, fisherman's cottage.The cottage is less than a mile from Windmill Point Marina, and five miles from the town of White Stone. You will enjoy the views of amazing wildlife, boaters, the beach, and breath-taking sunsets all while sitting on the back porch. The Cottage is nestled on a cove overlooking Little Bay and the mouth of Antipoison Creek. Come check out one of the Northern Neck's best kept secrets!

4–11 Nov

$232 NZD per night