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

Gwynn Holiday Rentals

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Our top choices for Gwynn holiday rentals

1. Campsite #4 At Blanchard Farm

Campsite #4 At Blanchard Farm
Diggs
The price is NZ$59
includes taxes & fees
8 Nov - 9 Nov
Campsite #4 At Blanchard Farm

2. 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 NZ$467
includes taxes & fees
5 Nov - 6 Nov
Luxury Studio Guesthouse, Walk to Museum, Boat Parking

3. Campsite #3 At Blanchard Farm

Campsite #3 At Blanchard Farm
Diggs
The price is NZ$59
includes taxes & fees
18 Nov - 19 Nov
Campsite #3 At Blanchard Farm

4. 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 NZ$488
includes taxes & fees
17 Nov - 18 Nov
Belle Haven - High Speed internet, walk to town

5. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
Gloucester
9.4 out of 10, Exceptional, (35 reviews)
"We loved the 1920’s feeling to the home. The cleanliness and quiet location were exactly what we were looking for. We were just a block from the historical center and took advantage of the shops and eateries. We would definitely stay here afain"
United States
David
The price is NZ$615
includes taxes & fees
8 Nov - 9 Nov
Radiant Gloucester House w/ Private Porch!

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

Nice 3-bedroom house with AC in peaceful Hartfield
Hartfield
The price is NZ$626
includes taxes & fees
5 Nov - 6 Nov
Nice 3-bedroom house with AC in peaceful Hartfield

7. 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 NZ$490
includes taxes & fees
8 Nov - 9 Nov
Deltaville 2BR Retreat, Walk to Museum, Boat Parking

8. 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 NZ$809
includes taxes & fees
11 Nov - 12 Nov
Bay Dream Believer Cottage on Beautiful East River Waterfront

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

The Bungalow, Pool, Dock, Kayaks, & Game Room
Topping
The price is NZ$591
includes taxes & fees
8 Nov - 9 Nov
The Bungalow, Pool, Dock, Kayaks, & Game Room

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

Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~
Kilmarnock
10.0 out of 10, Exceptional, (7 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$654
includes taxes & fees
8 Nov - 9 Nov
Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~

11. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
3.0 star property
Gloucester
The price is NZ$638
includes taxes & fees
14 Nov - 15 Nov
Radiant Gloucester House w/ Private Porch!

12. 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 NZ$324
includes taxes & fees
8 Nov - 9 Nov
Private home on creek with dock.

13. 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.
RivahMojo on Mill Creek-just off RappahannockRiver

14. The Nook in Kilmarnock Va 3 bedroom

The Nook in Kilmarnock Va 3 bedroom
Kilmarnock
10.0 out of 10, Exceptional, (9 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 NZ$801
includes taxes & fees
5 Nov - 6 Nov
The Nook in Kilmarnock Va 3 bedroom

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, (97 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 NZ$617
includes taxes & fees
8 Nov - 9 Nov
Restored 1930s Cottage on 1 Acre w/ Fire Pit

16. 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 NZ$513
includes taxes & fees
5 Nov - 6 Nov
The Waverly Tree House

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)
"The hosts made sure that everything in the house made one feel comfortable and at home. The view is fantastic and the landscaping with the rose garden and pool on a sunny day is inviting and relaxing. We enjoyed our stay "
United States
Mary S.
The price is NZ$913
includes taxes & fees
8 Nov - 9 Nov
Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden

18. Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool
Exmore
10.0 out of 10, Exceptional, (79 reviews)
"We loved our stay. We have stayed here multiple times over the years and our entire family, including the dog look forward to it. Hope to return."
United States
Jayson J.
The price is NZ$766
includes taxes & fees
1 Dec - 2 Dec
Nassawadox Creek Waterfront Home with Private Pool

19. Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
9.2 out of 10, Wonderful, (27 reviews)
"Peaceful and quiet with amazing views!"
United States
Eileen D.
The price is NZ$750
includes taxes & fees
13 Nov - 14 Nov
Smith Beach cottage w/ private sunset
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

Find out more about Gwynn

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Gwynn holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Gwynn. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Gwynn. Seeing all the best attractions is bound to make you fall in love with Gwynn. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Gwynn short-term rentals, that won’t be hard to do.

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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.