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

Gwynn Vacation 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 vacation rentals

1. Riverfront Cottage: Fire Pit & Kayaks

Riverfront Cottage: Fire Pit & Kayaks
3.0 star property
Deltaville
Riverfront Cottage: Fire Pit & Kayaks

2. 1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town

1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town
Mathews
10.0 out of 10, Exceptional, (42 reviews)
"The house was cozy, clean, and welcoming. Would definitely recommend! Rooms were all very spacious. "
United States
Casey J.
The price is CA $169
CA $460 total
includes taxes & fees
Oct 14 - Oct 15
1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town

3. Campsite #4 At Blanchard Farm

Campsite #4 At Blanchard Farm
Diggs
The price is CA $26
CA $60 total
includes taxes & fees
Oct 18 - Oct 19
Campsite #4 At Blanchard Farm

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

Nice 3-bedroom house with AC in peaceful Hartfield
Hartfield
The price is CA $168
CA $343 total
includes taxes & fees
Oct 11 - Oct 12
Nice 3-bedroom house with AC in peaceful Hartfield

5. Campsite #3 At Blanchard Farm

Campsite #3 At Blanchard Farm
Diggs
The price is CA $26
CA $60 total
includes taxes & fees
Oct 18 - Oct 19
Campsite #3 At Blanchard Farm

6. RV Site On Blanchard Farm -MAX RV LENGTH 24 FT

RV Site On Blanchard Farm -MAX RV LENGTH 24 FT
Diggs
RV Site On Blanchard Farm -MAX RV LENGTH 24 FT

7. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
Gloucester
9.4 out of 10, Exceptional, (33 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 CA $179
CA $521 total
includes taxes & fees
Oct 15 - Oct 16
Radiant Gloucester House w/ Private Porch!

8. 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 CA $281
CA $624 total
includes taxes & fees
Oct 12 - Oct 13
RivahMojo on Mill Creek-just off RappahannockRiver

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

Belle Haven - High Speed internet, walk to town
Kilmarnock
10.0 out of 10, Exceptional, (41 reviews)
"Great cottage, beautiful place to stay at"
United States
Darren W.
The price is CA $154
CA $433 total
includes taxes & fees
Oct 22 - Oct 23
Belle Haven - High Speed internet, walk to town

10. 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 CA $178
CA $501 total
includes taxes & fees
Oct 13 - Oct 14
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 CA $240
CA $510 total
includes taxes & fees
Oct 16 - Oct 17
Radiant Gloucester House w/ Private Porch!

12. The Nook in Kilmarnock Va 3 bedroom

The Nook in Kilmarnock Va 3 bedroom
Kilmarnock
10.0 out of 10, Exceptional, (7 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 CA $242
CA $678 total
includes taxes & fees
Oct 14 - Oct 15
The Nook in Kilmarnock Va 3 bedroom

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

The Bungalow, Pool, Dock, Kayaks, & Game Room
Topping
The price is CA $321
CA $609 total
includes taxes & fees
Oct 18 - Oct 19
The Bungalow, Pool, Dock, Kayaks, & Game Room

14. 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 CA $391
CA $786 total
includes taxes & fees
Oct 12 - Oct 13
Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden

15. 9BR Waterfront Oasis! Pickleball, Hot tub, Sauna & Theater

9BR Waterfront Oasis! Pickleball, Hot tub, Sauna & Theater
North
8.6 out of 10, Excellent, (14 reviews)
"The house was perfect for my coworkers and I who were in the area for work for a couple days. Jessica was friendly and communicated well. Would recommend for anyone looking for a lot of space to relax in a quiet area."
United States
Jonas M.
9BR Waterfront Oasis! Pickleball, Hot tub, Sauna & Theater

16. 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 CA $188
CA $524 total
includes taxes & fees
Oct 15 - Oct 16
Restored 1930s Cottage on 1 Acre w/ Fire Pit

17. Waterfront Retreat with Office and Private Dock, Boats!

Waterfront Retreat with Office and Private Dock, Boats!
Weems
9.8 out of 10, Exceptional, (28 reviews)
"Nicely equipped, well stocked, clean and neat. Good location with a canoe and kayaks to get out on the cove. Close drive to the three towns in the area with a number of good lunch/dinner spots. Host was very helpful."
United States
Ron H.
The price is CA $360
CA $704 total
includes taxes & fees
Oct 15 - Oct 16
Waterfront Retreat with Office and Private Dock, Boats!

18. Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
9.4 out of 10, Exceptional, (24 reviews)
"Gorgeous property and excellent host!"
United States
Ryan M.
The price is CA $224
CA $631 total
includes taxes & fees
Oct 18 - Oct 19
Smith Beach cottage w/ private sunset

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 CA $299
CA $511 total
includes taxes & fees
Oct 14 - Oct 15
The Waverly Tree House

20. 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 CA $348
CA $1,800 total
includes taxes & fees
Oct 12 - Oct 13
Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Gwynn?

Yes, we give you a choice of vacation rentals near the most popular sights in Gwynn, or you can select a more secluded option if you want a relaxing place to stay. Gwynn is known for its museums.

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

Gwynn's Island Gem | Private Beach & Bay Views: This highly rated vacation home rental in Gwynn is located on the waterfront and has a patio, a barbecue grill, 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 you can cook with friends or family.

How many vacation rentals are there in Gwynn?

Choose from 9 Expedia vacation rentals in Gwynn for a memorable vacation.

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 larger area, you’ll find Gwynn's Island Museum and Deltaville Marina.

What are vacation rentals like in Gwynn?

Vacation rentals are privately owned accommodations you can book for a short or long stay in Gwynn. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for families.