Vacation rentals in Gwynn

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Gwynn

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

Guest favorite

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 guest apartment (The Spat) for 4 people available for extra cost. Ask re: price/availability.

Dec 8 – 15

ﺩ.ﺇ482 per night
Guest favorite

Home in Grimstead

4.85 out of 5 average rating, 260 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.

Aug 29 – Sep 5

ﺩ.ﺇ1,507 per night
Guest favorite

Apartment in North

4.97 out of 5 average rating, 187 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!

Oct 16 – 23

ﺩ.ﺇ388 per night

Popular amenities for Gwynn vacation rentals

Stay near Gwynn's top sights

Hole in the Wall37 locals recommend
Gwynn's Island Museum11 locals recommend
Island Seafood4 locals recommend

Other great vacation rentals in Gwynn

Guest favorite

Cottage in Gwynn

4.92 out of 5 average rating, 24 reviews

Sunset Haven

Aug 29 – Sep 5

ﺩ.ﺇ657 per night
Guest favorite

Home in Gwynn

4.98 out of 5 average rating, 60 reviews

‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi

Dec 18 – 25

ﺩ.ﺇ1,169 per night
Guest favorite

Home in Gwynn

5.0 out of 5 average rating, 19 reviews

Island Oasis!

Nov 13 – 20

ﺩ.ﺇ1,333 per night
Guest favorite

Cottage in Gwynn

4.96 out of 5 average rating, 26 reviews

Island Get-A-Way on the Chesapeake Bay with Beach

Sep 8 – 15

ﺩ.ﺇ1,132 per night
Guest favorite

Vacation home in Gwynn

4.93 out of 5 average rating, 27 reviews

Waterfront, Dock, Hot Tub, Fire Pit, Beach Access!

May 29 – Jun 5

ﺩ.ﺇ1,859 per night
Guest favorite

Home in North

5.0 out of 5 average rating, 35 reviews

The Llama House

Sep 11 – 18

ﺩ.ﺇ423 per night
Guest favorite

Home in Hudgins

4.87 out of 5 average rating, 15 reviews

2 bedroom waterfront bay house with view

Apr 15 – 22

ﺩ.ﺇ671 per night
Guest favorite

Tiny home in Diggs

4.93 out of 5 average rating, 84 reviews

Stargazer Tiny Cabin

May 6 – 13

ﺩ.ﺇ517 per night
Superhost

Home in Hudgins

4.82 out of 5 average rating, 96 reviews

The Big Boathouse on a Point

Nov 9 – 16

ﺩ.ﺇ1,330 per night
Guest favorite

Home in Deltaville

4.89 out of 5 average rating, 19 reviews

Delta Breeze

Oct 2 – 9

ﺩ.ﺇ523 per night
Guest favorite

Cottage in Moon

4.89 out of 5 average rating, 79 reviews

Blue Moon Haven- Cozy Vintage Cottage in Mathews

Jun 11 – 18

ﺩ.ﺇ527 per night
Guest favorite

Cottage in Deltaville

5.0 out of 5 average rating, 62 reviews

Unique & bright two-bedroom waterfront cottage

Feb 27 – Mar 6

ﺩ.ﺇ953 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Mathews County
  5. Gwynn