Beachfront holiday rental in Gwynn Island

Find and book unique beachfront homes on Airbnb

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Popular amenities for Gwynn Island beachfront rentals

Pet-friendly beachfront home rentals

Top Guest favourite
Home in Hudgins
5 out of 5 average rating, 9 reviews

Water front Coastal Bungalow with boat docks

KaraRating, 5 stars4 weeks ago
This was one of the cleanest, well thought out Airbnbs my Husband and I have ever stayed in! The host was quick to respond with any needs, the home was well stocked with essentials, and had notes with recommendations for the area. We loved drinking coffee on the dock and watching movies in the outdoor living area. The area is so quiet and peaceful.
Top Guest favourite
Guesthouse in Cobbs Creek
4.94 out of 5 average rating, 17 reviews

Piankatank Riverfront Perch in Mathews County, VA

MichaelRating, 5 starstoday
Thank you for a wonderful night away at the rivah! Just what our family needed.
Superhost
Cottage in Reedville
4.88 out of 5 average rating, 210 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

LorenRating, 5 stars1 week ago
We loved out time at this Bayside home. My boys spent outside upon hours at the little private beach, where the water doesn't really get deep for quite a ways and the waves were never very rough. it was perfect for them. we all enjoyed the hot tub, kayaks, comfortable beds. My personal favorite was the hammock right by the water, listening to nothing but the waves and the calls of the ospreys that made the area their home. Forget the overly built up touristy areas and give this place a try. You will not regret it.
Guest favourite
Cabin in Gloucester
4.95 out of 5 average rating, 19 reviews

Bill's Island

GeorgiaRating, 5 stars3 weeks ago
'A diamond in the ruff'. Our first AirBnB and we absolutely loved the cabin. Had everything we needed & very clean. We had wonderful weather, nice breeze off the water. Fish were biting. Very quiet . A great getaway cabin. Our hostess Lorena was great, checked on us to see if we needed anything. Well stocked kitchen. Thank You Lorena!
Top Guest favourite
Guest suite in Dunnsville
5 out of 5 average rating, 269 reviews

The Bird's Nest at Holly Bluff-Riverfront. Beach.

AkaleiRating, 5 stars1 month ago
T’s place was absolute perfection! It was beautiful, tastefully decorated and the homemade muffins and cookies were amazing! She and John were so lovely and accommodating. Relaxing on the dock on the river was a sublime experience as well! I really can’t say enough about my time spent there and if I’m ever in the area again I will definitely be staying at T’s! Why would you stay anywhere else!?
Guest favourite
Home in Cape Charles
4.95 out of 5 average rating, 144 reviews

Harbor View- (Sun - Sun rental June- Aug.)

TheresaRating, 5 stars3 weeks ago
We absolutely loved the stay at Janie’s place! It was great and such a short walk to the beach. The beach wagon, chairs, and umbrellas were a nice touch and saved us from having to bring our own! There is also a propane and charcoal grill available for use, which is amazing. We look forward to booking our next trip to Cape Charles here, hopefully sooner rather than later! We have heard Christmas time is beautiful!
Superhost
Cottage in Lottsburg
4.9 out of 5 average rating, 102 reviews

Charming Waterfront Home with Expansive Views

MichaelRating, 5 stars6 months ago
We loved the house; cozy, nicely decorated, with many pieces of original art that really added character. The kitchen is well stocked for those who like to cook. The location right on the water was wonderful, and Nancy provided kayaks, which we took advantage of. Our dog was beside himself with so much room to run. Nancy’s daughter and family live next door, and we spent quite a few hours enjoying conversation and local knowledge with them. We would go back again.
Guest favourite
Cottage in Reedville
4.89 out of 5 average rating, 46 reviews

Waterfront Bay Cottage w/ Your Own Private Beach

BrandonRating, 5 stars3 weeks ago
We had a fantastic stay at this charming cottage on a private beach! The peaceful setting and direct access to the water made for a truly relaxing getaway. We especially loved the Adirondack chairs and firepit overlooking the Chesapeake Bay—perfect for amazing views and cozy evenings. The master bedroom and living spaces offered beautiful water views that made every moment feel serene and special. The owner was incredibly accommodating with check-in and shared thoughtful, personal tips that made our stay even more enjoyable. Highly recommend this spot for anyone looking to unwind by the bay!

Beachfront home rentals with a pool

Home in Heathsville
5 out of 5 average rating, 10 reviews

Gorgeous Historic Riverfront House

RobinRating, 5 stars45 months ago
My daughter found this gem online to book for my 65th birthday and a family get-together on the Northern Neck. We stay in Airbnb homes quite frequently all over the world and this is the loveliest home we've had the good fortune to stay in. Christine is the most gracious host and this home is special because she has made it that way for her family. It's a huge difference to stay in a vacation home that the host rents and a home that the host lives in. Christine's eye for beauty is exquisite and the home is comfortable as well as beautiful. It seldom happens that you say, "I wish the house had (fill in the blank)" and this house has it. The river is a gorgeous backdrop and there are kayaks to use. The saltwater pool is a great addition and a reason to hang at the house. And there is everything one needs to knock out a meal or if you don't want to cook, plenty of places to eat in the area. All in all, this house is a 15 out of 10!!
Top Guest favourite
Home in Heathsville
5 out of 5 average rating, 10 reviews

Waterfront Escape Pool Dock Kayaks Chesapeake Bay

KarenRating, 5 stars2 weeks ago
My family and I had a terrific stay. The house was very accommodating, clean, and comfortable. Allison was a great help and responded quickly to every inquiry. The outdoor space is great - we used the fire pit every night and I brought my boat and kept it at the dock. We would definitely stay here again!
Home in White Stone

Rappahannock River House

LizbethRating, 5 stars19 months ago
Great host and great stay! Would definitely stay here again!
Guest favourite
Home in Cape Charles
5 out of 5 average rating, 17 reviews

Coastal Soul/spacious/updated/perfect beach escape

RobertRating, 5 stars7 months ago
Excellent house in Cape Charles. The house was able to accommodate our group comfortably. Our only regret was not being able to stay longer.
Home in Heathsville
5 out of 5 average rating, 4 reviews

18 Acre Wood

NicoleRating, 5 stars1 month ago
This home was amazing - Jack and Beth were wonderful - everything we needed was right there - game room was perfect for the kids - the house was tremendous and spotless and perfect and I can’t say enough great things about my experience. I would 110% recommend this home to anyone!! Book it!!!
Home in Cape Charles
5 out of 5 average rating, 8 reviews

Handicap Accesible, with Beach, Pool & Tennis!

JRating, 5 stars8 months ago
Blue Belle was a fun and roomy place to spend a long weekend with our family! It’s in a great area and was easy to get anywhere you wanted to go in Cape Charles. We rented a golf cart but it wasn’t in the best of shape. That’s not Doug’s fault but that of the rental company. Therefore, we didn’t really use it as much as we would have liked. Doug was prompt in getting the washing machine repaired and it was needed. Our granddaughters enjoyed playing the ring on a string game on the back porch and walk to the beach nearby. I recommend staying here!
Home in Gloucester County
4.63 out of 5 average rating, 52 reviews

Private 5-acre Waterfront Peninsula with Beach

TroyRating, 5 stars1 month ago
This was a short trip for a bachelor/bachelorette party. Everyone who was coming was so impressed and was like we wish we were staying here longer than one night! Mary was very responsive and even popped out and said welcome when we arrived! Definitely would recommend this place for a fun get away! The bonfire was definitely a recommended opportunity! Thank you again Mary!!
Superhost
Cottage in Heathsville
4.84 out of 5 average rating, 80 reviews

Riverfront Retreat with PRIVATE POOL and BEACH!!

YVisRating, 5 stars3 weeks ago
Awesome place with my t, we had everything we needed and more. Great location to disconnect and connect with one another. Plenty of space, locals, location and great amenities.

Private beachfront home rentals

Guest favourite
Home in Lancaster
4.94 out of 5 average rating, 85 reviews

River Home on Sea Glass Beach

RosemarieRating, 5 stars2 weeks ago
We loved our mini vacation at Darrell’s. The home had everything one would need and it’s located in a quiet, private area with plenty to do. And one can’t not mention the friendly neighbors and beautiful surroundings. We would love to come back again. Thank you for hosting us!
Superhost
Cabin in Reedville
4.73 out of 5 average rating, 22 reviews

"Elderberries" Chesapeake Bayfront Cottage

JoelRating, 5 stars3 weeks ago
We enjoyed our stay here. Very quiet area, nice comfortable space. The gravel road leading in (maybe a half-mile long) and driveway gave us a good area for morning and evening dog walks. We did not end up doing any fishing but the pond looked like a great place for kayak fishing. Not specific to the house but in the area: Rita's Cafe in Weems was great (food truck on a small road)--Chef Craige usually has a special and some regular menu items. Leadbellys (at Fairport Marina) had good oysters and hush puppies and was convenient for our first night. River Market in White Stone has good food to be ordered at the rear counter and prepared items in the coolers. Out of the Oven Bakery (White Stone) had great bread Miss Mary's seafood, also in White Stone had great fresh fish and prepared items. The three places in White Stone are very close to each other so convenient when running out.
Superhost
Townhouse in Cape Charles
4.55 out of 5 average rating, 235 reviews

2 Blocks to Beach in Cape Charles

KaytlynnRating, 5 stars1 month ago
We loved our visit to Cape Charles! This Airbnb was the perfect place for us and we were pleasantly surprised with the fended in backyard. The space was just a described and fit our needs perfectly. The fenced in back yard was perfect for our pups and the neighborhood was friendly and so peaceful! The walk to the beach was easy and the local shops and restaurants were fun as well! We hope to be back soon!
Guest favourite
Home in Heathsville
4.9 out of 5 average rating, 82 reviews

Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit!

ManuelRating, 5 stars4 months ago
We took a small vacation with my sister’s family and we loved the location. Our kids enjoyed the small play area in the basement with the arcade machine and foosball table. We cooked every night and they had all useful appliances. We used the Ninja air fryer and Keurig machine every day. Since we went in January after a snowstorm the road was a little hazardous to use and the lake was completely frozen, so we spent most times indoors. We did enjoy going to the dock and looking at the frozen lake. This will be a great place to visit during the summer, they had Kayaks to use and a nice dock to jump from and fish. We would definitely come back.
Guest favourite
Home in Jamaica
4.91 out of 5 average rating, 64 reviews

Waterfront Sandy Beach Retreat near Urbanna

NancyRating, 5 stars6 days ago
Karen was very quick to respond to our questions. The house was lovely. There were canoes, kayaks and water boards for the family to use. Baby pool for the kids. Fishing and crabbing was great entertainment for all. Kitchen well stocked with anything you needed.
Guest favourite
Cottage in Cape Charles
4.93 out of 5 average rating, 27 reviews

The Crew's Quarters: Steps from the Bay

SueRating, 5 stars1 week ago
Caryn’s home was perfect for our needs. She was very responsive to our question and provided valuable information about the area.
Superhost
Cottage in Heathsville
4.7 out of 5 average rating, 23 reviews

I Love to Fish on Chesapeake Bay -New House

PeterRating, 5 stars34 months ago
This is a great place if your family is looking for a beach get away. The fishing pier is large and can accommodate multiple fishing poles. The crabbing was also great! We caught so many crabs that we had crabs everyday. The large dining table and screened porch was perfect for family lunches/dinners. Rangeley (host) was also very responsive and made sure our stay was comfortable. I would highly recommend this place!
Guest favourite
Home in Cape Charles
5 out of 5 average rating, 24 reviews

Bayfront Family Retreat - best porch in town

ChrisRating, 5 stars1 week ago
Lovely home very close to the beach in an awesome little beach town. We had a great stay and would come back again.

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Mathews County
  5. Gwynn
  6. Gwynn Island
  7. Beachfront rentals