A pier extending into calm waters at sunset with a clear sky.

Gwynn Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Gwynn holiday rentals

A small, single-story house with a red door, a porch with a white railing, and a number '70' sign.

1. Luxury Studio Guesthouse, Walk to Museum, Boat Parking

Luxury Studio Guesthouse, Walk to Museum, Boat Parking
Deltaville
10.0 out of 10, Exceptional, (61 reviews)
"Awesome little place. We absolutely enjoyed staying here. Very clean and had all amenities one would need. Will definitely book again. "
United States
Stan R.
The price is AU$423
includes taxes & fees
3 Nov - 4 Nov
Luxury Studio Guesthouse, Walk to Museum, Boat Parking
A hammock tied between two trees in a forested area.

2. Campsite #4 At Blanchard Farm

Campsite #4 At Blanchard Farm
Diggs
The price is AU$63
includes taxes & fees
29 Oct - 30 Oct
Campsite #4 At Blanchard Farm
A bedroom with a bed, bedside tables, a window with curtains, a patterned rug, and a ceiling vent.

3. Belle Haven - High Speed internet, walk to town

Belle Haven - High Speed internet, walk to town
Kilmarnock
10.0 out of 10, Exceptional, (42 reviews)
"Great cottage, beautiful place to stay at"
United States
Darren W.
The price is AU$413
includes taxes & fees
25 Oct - 26 Oct
Belle Haven - High Speed internet, walk to town
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

4. Nice 3-bedroom house with AC in peaceful Hartfield

Nice 3-bedroom house with AC in peaceful Hartfield
Hartfield
The price is AU$342
includes taxes & fees
29 Oct - 30 Oct
Nice 3-bedroom house with AC in peaceful Hartfield
A kitchen with dark blue cabinets, a gas stove, a sink, and a window overlooking the backyard.

5. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
Gloucester
9.4 out of 10, Exceptional, (34 reviews)
"This is a very comfortable clean home in a nice quiet neighborhood. It’s very close to some excellent restaurants and places of interest. We especially enjoyed the sunroom."
United States
Joseph B.
The price is AU$505
includes taxes & fees
25 Oct - 26 Oct
Radiant Gloucester House w/ Private Porch!
A front door with a wreath, a wooden porch, and a gravel pathway.

6. Bay Dream Believer Cottage on Beautiful East River Waterfront

Bay Dream Believer Cottage on Beautiful East River Waterfront
Mathews
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful location, host communicated well"
United States
Nicole K.
The price is AU$662
includes taxes & fees
3 Nov - 4 Nov
Bay Dream Believer Cottage on Beautiful East River Waterfront
A hammock tied between two trees in a forested area.

7. Campsite #3 At Blanchard Farm

Campsite #3 At Blanchard Farm
Diggs
The price is AU$63
includes taxes & fees
3 Nov - 4 Nov
Campsite #3 At Blanchard Farm
A porch with two rocking chairs, a black door, and a mailbox.

8. The Nook in Kilmarnock Va 3 bedroom

The Nook in Kilmarnock Va 3 bedroom
Kilmarnock
10.0 out of 10, Exceptional, (8 reviews)
"This home is comfortable, well appointed, and in a great location. Host is accommodating and communicates appropriately I highly recommend this property!"
United States
Anonymous traveller
The price is AU$674
includes taxes & fees
26 Oct - 27 Oct
The Nook in Kilmarnock Va 3 bedroom
A dining area with a view of a lake and trees, featuring white tables and benches, ceiling fans, and large windows.

9. RivahMojo on Mill Creek-just off RappahannockRiver

RivahMojo on Mill Creek-just off RappahannockRiver
Topping
10.0 out of 10, Exceptional, (26 reviews)
"Property was lovely, host very responsive, couldn’t ask for more!"
United States
Donna B.
The price is AU$606
includes taxes & fees
27 Oct - 28 Oct
RivahMojo on Mill Creek-just off RappahannockRiver
A small, single-story house with a porch, a wooden deck, and a brick pathway.

10. Deltaville 2BR Retreat, Walk to Museum, Boat Parking

Deltaville 2BR Retreat, Walk to Museum, Boat Parking
Deltaville
10.0 out of 10, Exceptional, (75 reviews)
"Everything was perfect - loved staying here. "
United States
John L.
The price is AU$445
includes taxes & fees
8 Nov - 9 Nov
Deltaville 2BR Retreat, Walk to Museum, Boat Parking
A kitchen with dark blue cabinets, a gas stove, a sink, and a window overlooking the backyard.

11. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
3.0 star property
Gloucester
The price is AU$510
includes taxes & fees
1 Nov - 2 Nov
Radiant Gloucester House w/ Private Porch!
A modern kitchen with a central island, stainless steel appliances, and teal bar stools.

12. Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~

Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~
Kilmarnock
10.0 out of 10, Exceptional, (6 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 AU$532
includes taxes & fees
3 Nov - 4 Nov
Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~
A wooden dock with chairs facing a calm lake, surrounded by dense forest.

13. Private home on creek with dock.

Private home on creek with dock.
Lancaster
9.2 out of 10, Wonderful, (15 reviews)
"Great place loved it!"
United States
Brandon W.
The price is AU$298
includes taxes & fees
15 Nov - 16 Nov
Private home on creek with dock.
A covered outdoor area with a pool, wicker furniture, and large windows offering a view of the outdoors.

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

The Bungalow, Pool, Dock, Kayaks, & Game Room
Topping
The price is AU$495
includes taxes & fees
24 Oct - 25 Oct
The Bungalow, Pool, Dock, Kayaks, & Game Room
A covered porch with wooden benches and chairs, large windows, and a view of a grassy area.

15. Restored 1930s Cottage on 1 Acre w/ Fire Pit

Restored 1930s Cottage on 1 Acre w/ Fire Pit
Hayes
9.6 out of 10, Exceptional, (95 reviews)
"Our family of 6 (age range 20’s to 80’s) enjoyed all of the rooms and porches. The air conditioners kept the home comfortable and the porches were cozy for those who like it warmer. We liked the convenience of being able to make our own breakfasts and dinners here. Having a grill was a bonus."
United States
Susan C.
The price is AU$512
includes taxes & fees
26 Oct - 27 Oct
Restored 1930s Cottage on 1 Acre w/ Fire Pit
A small, single-story house with a porch, a wooden deck, and a brick pathway.

16. Two Private Cottages 3BR, Boat Parking, Walk to Marinas

Two Private Cottages 3BR, Boat Parking, Walk to Marinas
Deltaville
10.0 out of 10, Exceptional, (1 review)
"Clean house, comfy"
United States
Ellen M.
The price is AU$757
includes taxes & fees
1 Nov - 2 Nov
Two Private Cottages 3BR, Boat Parking, Walk to Marinas
A wooden picnic table with a pitcher, glasses, and a plate set on a grassy area by a body of water.

17. Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden

Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden
Locust Hill
10.0 out of 10, Exceptional, (41 reviews)
"We are a Family of 4 that stayed and absolutely loved Rosehill Cottage! Set back in a serene setting with the most beautiful view of the Rappahannock River! The Cottage was adorable with plenty of space to spread out, was clean, & had all of the cooking ware you need. The pool was a blast! We really enjoyed our time at the pool! I would definitely give Rosehill Cottage a consideration when you want to get away from the hustle & bustle of everyday life!"
United States
Melody F.
The price is AU$719
includes taxes & fees
26 Oct - 27 Oct
Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden
A wooden deck with a white fence and a lounge chair, overlooking a calm body of water during sunset.

18. Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
9.4 out of 10, Exceptional, (25 reviews)
"Peaceful and quiet with amazing views!"
United States
Eileen D.
The price is AU$618
includes taxes & fees
28 Oct - 29 Oct
Smith Beach cottage w/ private sunset
A wooden deck with a chair, a welcome mat, and a view of a forest.

19. The Waverly Tree House

The Waverly Tree House
Machipongo
10.0 out of 10, Exceptional, (3 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 AU$470
includes taxes & fees
28 Oct - 29 Oct
The Waverly Tree House
A house surrounded by dense greenery and a small dock extending into a body of water.

20. Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool
Exmore
10.0 out of 10, Exceptional, (77 reviews)
"It was a beautiful setting there. We loved the pool. Manager was very friendly n welcoming."
United States
Rita T.
The price is AU$651
includes taxes & fees
1 Nov - 2 Nov
Nassawadox Creek Waterfront Home with Private Pool
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.
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Top Gwynn Hotel Reviews

Waterfront Cottage w Private Beach on Chesapeake Bay!

Waterfront Cottage w Private Beach on Chesapeake Bay!

10/10 Excellent
"The cottage is truly a magical place, especially for those with a water-loving dog that also loves to roll or lay in the grass! We’ve been here multiple times, and as always, the cottage was in great shape and the host was so communicative and responsive—before, during, and after our stays. We always think about when we can return again after each of our stays. It’s truly a cozy and comfortable home away from home with magnificent views of the bay/river. Don’t miss the sunsets from the cottage!"
Ji B. 5-night trip
Posted 2 days ago
Waterfront Cottage w Private Beach on Chesapeake Bay!

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 favourite 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 depend 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 AU$512 per night. Entering your travel dates in the search wizard might find you 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?

Gwynn's Island Gem | Private Beach & Bay Views: This highly rated holiday home rental in Gwynn is located on the waterfront, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Gwynn?

Choose from 9 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.