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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Browse Select Gwynn Vacation Homes

Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
Exterior

Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

9.6 out of 10, Exceptional, (164)
"We throughly enjoyed our time at the little blue house! We would definitely stay here again."
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
Charming 2-bedroom house on the Chesapeake Bay
Exterior

Charming 2-bedroom house on the Chesapeake Bay

9.4 out of 10, Exceptional, (10)
"Property was very nice and has a lot history with it. "
Charming 2-bedroom house on the Chesapeake Bay
Nassawadox Creek Waterfront Home with Private Pool
Outdoor pool

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (53)
"We had everything we needed. A very quiet, relaxing weekend. "
Nassawadox Creek Waterfront Home with Private Pool
Boat Dock & Kayaks: Waterfront Home in Deltaville!
Fridge, microwave, stovetop, dishwasher

Boat Dock & Kayaks: Waterfront Home in Deltaville!

10.0 out of 10, Exceptional, (1)
"Great place to stay for the weekend. Place was quiet and peaceful. The house furnished well with great amenities. Fishing and kayaking from off the dock. Also life jackets available for the kids for safety as well. Catching crabs off the docks, fishing, kayaking, paddle boarding. The house has nice deck in the back where we enjoyed morning coffee and afternoon and evening activities playing corn hole, and spent good time sitting in front of fire pit was great. It was pleasure to stay spent...
Boat Dock & Kayaks: Waterfront Home in Deltaville!
Charming 3-bedroom house in Deltaville with Stunning Views and Beautiful garden!
Property grounds

Charming 3-bedroom house in Deltaville with Stunning Views and Beautiful garden!

2.0 star property
10.0 out of 10, Exceptional, (6)
"We thoroughly enjoyed our weekend. The house was lovely and clean, and the lawn and dock were perfect for getting some sun and watching the ospreys tend their nest. Aaron greeted us and made us feel welcome and responded to the one or two questions we had during our stay. "
Charming 3-bedroom house in Deltaville with Stunning Views and Beautiful garden!
Charming and spacious 4-bedroom farm retreat with horses - Relax and Unwind!
Dining

Charming and spacious 4-bedroom farm retreat with horses - Relax and Unwind!

10.0 out of 10, Exceptional, (11)
"Nice, clean place with thoughtful touches, plenty of space, and amazing grounds. The owner was kind enough to let the kids meet the new puppies. Definitely would stay again stay "
The price is CA $243
CA $426 total
includes taxes & fees
Sep 21 - Sep 22
Charming and spacious 4-bedroom farm retreat with horses - Relax and Unwind!
Charming 2-bedroom house with AC, WiFi in Mathews County Virginia
Sun loungers, beach towels

Charming 2-bedroom house with AC, WiFi in Mathews County Virginia

10.0 out of 10, Exceptional, (6)
Charming 2-bedroom house with AC, WiFi in Mathews County Virginia
Spectacular Riverfront Retreat with Kid-Friendly Beach. Enjoy the ‘Riva Life’!
Fridge, microwave, oven, stovetop

Spectacular Riverfront Retreat with Kid-Friendly Beach. Enjoy the ‘Riva Life’!

10.0 out of 10, Exceptional, (189)
"Every Mother’s Day our extended family leaves town to explore a new part of Virginia for the weekend. Our stay in Bohannon could change all that. We want to go back! This is a lovely and spacious home with a million thoughtful touches. The property itself is spectacular and our gang enjoyed the kayaks, paddle boat and fire pit. We rate this as our top Mother’s Day getaway so far and we’ve been doing this for six years! Highly recommend! "
Spectacular Riverfront Retreat with Kid-Friendly Beach. Enjoy the ‘Riva Life’!
Spacious waterfront home with dock and sunset view
Outdoor dining

Spacious waterfront home with dock and sunset view

9.4 out of 10, Exceptional, (6)
"Overall, we found the home to be very accommodating with outstanding water views! Plenty of bedrooms!The following suggestions are given in the spirit of making the rental more guest friendly.Make available a book or sheet with house rules, passwords, and helpful hints for local restaurants and shoppingBathroom hooks to hang clothes and towelsTubs are slippery! Non slip mates should be addedAdd bath soap bars to go with liquid soap and shampoos Bedrooms should have full length mirrors as the...
Spacious waterfront home with dock and sunset view
Cozy cottage on the Chesapeake Bay
Property grounds

Cozy cottage on the Chesapeake Bay

9.8 out of 10, Exceptional, (47)
"Easy access to the property and to town. Very quite and comfy."
Cozy cottage on the Chesapeake Bay
Great home for holidays! Large kitchen, firepit & hot tub, beautiful water views
Outdoor pool

Great home for holidays! Large kitchen, firepit & hot tub, beautiful water views

9.8 out of 10, Exceptional, (45)
"We lived the property and the host was extremely helpful and everything was as expected. I highly recommend this vacation home! "
Great home for holidays! Large kitchen, firepit & hot tub, beautiful water views
Magical wooded cottage pool +priv hottub walk2town
Pool

Magical wooded cottage pool +priv hottub walk2town

10.0 out of 10, Exceptional, (25)
"Great place for a weekend get away!"
Magical wooded cottage pool +priv hottub walk2town
Luxury Studio Guesthouse Deltaville
Interior

Luxury Studio Guesthouse Deltaville

10.0 out of 10, Exceptional, (57)
"This little house is still roomy and perfect for a stay. Nothing to complain about would stay again and highly recommend "
The price is CA $191
CA $415 total
includes taxes & fees
Sep 1 - Sep 2
Luxury Studio Guesthouse Deltaville
Chesapeake Bay Beachfront Retreat
On the beach, sun loungers, beach towels

Chesapeake Bay Beachfront Retreat

9.4 out of 10, Exceptional, (140)
"This was the second year in a row we have stayed here, and we absolutely loved it! The house was clean and smelled so fresh when we arrived, and the location is so beautiful. We really enjoyed the peaceful atmosphere, and the fishing was fantastic. Diane is a wonderful host, and we hope to stay here again in the future!"
Chesapeake Bay Beachfront Retreat
Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!
On the beach, sun loungers

Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!

10.0 out of 10, Exceptional, (30)
"We have enjoyed 2 stays at the cottage. It is a wonderful location and the owners have been great and are very thoughtful. The beach is perfect, and we love the neighborhood. We can't wait to visit again!"
Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!
Bayfront Escape, Private Dock, Large Deck, and Views!
Terrace/patio

Bayfront Escape, Private Dock, Large Deck, and Views!

10.0 out of 10, Exceptional, (1)
"This house has beautiful views and it was only about 45 min to Williamsburg. It is on Hills Bay, which flows into the Chesapeake Bay. The water is very shallow and would be great for younger kids. We brought kayaks and enjoyed our time on the water. It would be fantastic for someone that owns a boat too. The water doesn’t have many waves, but we tied a party size float to part of the dock and all the kids, ages 10-19, loved our time there. Since I’m the first review, I think I might be the first...
Bayfront Escape, Private Dock, Large Deck, and Views!
Fantastic waterfront home on Jackson Creek
Fridge, microwave, oven, stovetop

Fantastic waterfront home on Jackson Creek

10.0 out of 10, Exceptional, (51)
"The groomsmen for our daughters wedding stayed here. Everything was perfect! Hosts were great! "
Fantastic waterfront home on Jackson Creek
Steps away from Gloucester Marina & Restaurant
Exterior

Steps away from Gloucester Marina & Restaurant

10.0 out of 10, Exceptional, (33)
"Great house. Very clean and well stocked. Will stay again!"
Steps away from Gloucester Marina & Restaurant
Beach House Getaway, exclusive location on "Chesapeake Bay" with private beach
On the beach

Beach House Getaway, exclusive location on "Chesapeake Bay" with private beach

10.0 out of 10, Exceptional, (12)
"Sunrise and sunsets were beautiful!"
Beach House Getaway, exclusive location on "Chesapeake Bay" with private beach
Beach House on Chesapeake Bay!
On the beach, sun loungers, beach towels

Beach House on Chesapeake Bay!

10.0 out of 10, Exceptional, (130)
"Really enjoyed our stay and hope to return!"
Beach House on Chesapeake Bay!
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

Bay Dream Believer Cottage on Beautiful East River Waterfront

Bay Dream Believer Cottage on Beautiful East River Waterfront

10/10 Excellent
"Everything was perfect. "
Tracy J. 2-night trip
Posted 4 days ago
Bay Dream Believer Cottage on Beautiful East River Waterfront