Gwynn Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Gwynn holiday rentals

The Nook in Kilmarnock Va 3 bedroom

The Nook in Kilmarnock Va 3 bedroom
Kilmarnock
10.0 out of 10, Exceptional, (3 reviews)
"Easy check in and out. Owner was helpful. House was clean and well equipped. Beds were comfortable. Location was convenient and quiet. "
United States
Margaret K.
The price is NZ$776
includes taxes & fees
18 May - 19 May
The Nook in Kilmarnock Va 3 bedroom

Private home on creek with dock.

Private home on creek with dock.
Lancaster
8.6 out of 10, Excellent, (10 reviews)
"Beautiful little cottage on the river. Fantastic sunset views. Wonderful little retreat for couples!"
United States
Nathan
The price is NZ$503
includes taxes & fees
25 May - 26 May
Private home on creek with dock.

The Waverly Tree House

The Waverly Tree House
Machipongo
10.0 out of 10, Exceptional, (2 reviews)
"Very comfortable and clean spot. Great quiet morning views of the creak. We enjoyed a relaxing stay. It had everything we needed. "
United States
Jeanna C.
The price is NZ$598
includes taxes & fees
12 May - 13 May
The Waverly Tree House

Campsite #3 At Blanchard Farm

Campsite #3 At Blanchard Farm
Diggs
The price is NZ$70
includes taxes & fees
9 May - 10 May
Campsite #3 At Blanchard Farm

Fire Pit🔥 Walk to Town. 1st floor King Bed & Walk in Shower! Monthly Discounts!

Fire Pit🔥 Walk to Town. 1st floor King Bed & Walk in Shower! Monthly Discounts!
Mathews
10.0 out of 10, Exceptional, (38 reviews)
"Super cute and cozy! Nice to be able to walk to the courthouse area!"
United States
Jenn L.
The price is NZ$552
includes taxes & fees
19 May - 20 May
Fire Pit🔥 Walk to Town. 1st floor King Bed & Walk in Shower! Monthly Discounts!

Waterfront Home with stunning views & Hot tub- rent Golf Cart/Kayak/Boat

Waterfront Home with stunning views & Hot tub- rent Golf Cart/Kayak/Boat
Hayes
The price is NZ$886
includes taxes & fees
9 May - 10 May
Waterfront Home with stunning views & Hot tub- rent Golf Cart/Kayak/Boat

Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown

Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
Hayes
8.4 out of 10, Very good, (5 reviews)
"Great property. Waterfront with pier, huge yard, beautiful home with pool table, hot tub and projector set up. 100% would stay here again and recommend as would all of the family we had stay or visit us there. "
United States
Steve F.
The price is NZ$2,056
includes taxes & fees
9 May - 10 May
Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown

The Bungalow, Pool, Dock, Kayaks, & Game Room

The Bungalow, Pool, Dock, Kayaks, & Game Room
Topping
The price is NZ$717
includes taxes & fees
20 May - 21 May
The Bungalow, Pool, Dock, Kayaks, & Game Room

Hot Tub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~Kilmarnock Rivah Retreat

Hot Tub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~Kilmarnock Rivah Retreat
Kilmarnock
10.0 out of 10, Exceptional, (2 reviews)
"Nice rambler in a great in town location with hot tub, firepit, and fenced in yard. Also great value for the price. "
United States
Melinda H.
The price is NZ$837
includes taxes & fees
19 May - 20 May
Hot Tub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~Kilmarnock Rivah Retreat

Affordable Cottage!

Affordable Cottage!
Deltaville
The price is NZ$550
includes taxes & fees
10 May - 11 May
Affordable Cottage!

Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
10.0 out of 10, Exceptional, (1 review)
"The booking was fast and easy. When we got there the place was very clean and organized. I would totally recommend this location to friends and loved ones. We had a wonderful time there. The whole experience was great from booking to leaving."
United States
Jessika S.
The price is NZ$631
includes taxes & fees
21 May - 22 May
Smith Beach cottage w/ private sunset

Water front Oasis with pickle-ball court and hot tub

Water front Oasis with pickle-ball court and hot tub
North
9.2 out of 10, Wonderful, (10 reviews)
"We cooked all our meals using both kitchens and had plenty of room and supplies to do so. Absolutely loved the grill and outdoor seating arrangements. We had plenty of room for everyone and the home matched exactly as advertised. "
United States
Hunter G.
Water front Oasis with pickle-ball court and hot tub

Campsite #4 At Blanchard Farm

Campsite #4 At Blanchard Farm
Diggs
The price is NZ$70
includes taxes & fees
10 May - 11 May
Campsite #4 At Blanchard Farm

RV Site On Blanchard Farm -MAX RV LENGTH 24 FT

RV Site On Blanchard Farm -MAX RV LENGTH 24 FT
Diggs
The price is NZ$74
includes taxes & fees
9 May - 10 May
RV Site On Blanchard Farm -MAX RV LENGTH 24 FT
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Gwynn Hotel Reviews

Find out more about Gwynn

Everything you need to know about Gwynn holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gwynn holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gwynn holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Gwynn holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gwynn. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gwynn holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gwynn holiday rentals we have selected for you start as low as NZ$631 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Gwynn rentals

At Expedia, we put the best Gwynn holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Gwynn rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gwynn holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gwynn. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Gwynn?

Yes, there are holiday rentals close to the most popular sights in Gwynn, or you can select a more secluded option if you're looking for a relaxing stay. Gwynn is known for its museums.

What are some of the best holiday rentals that Gwynn has to offer?

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE: This holiday home rental outside of Gwynn offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Gwynn?

Choose from 8 Expedia holiday rentals in Gwynn for a memorable holiday.

What can I see and do in Gwynn?

Explore the area and family-friendly sights such as Deltaville Maritime Museum, or get out into nature at a spot like Chesapeake Bay. In the wider area, you’ll find Gwynn's Island Museum and Deltaville Marina.

What are holiday rentals like in Gwynn?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Gwynn. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.