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Gwynn Family & Kid Friendly Rentals

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    Don't let other travelers get your favorite Gwynn area vacation rental. You're so close to securing your perfect getaway. Book today.
    18 Matching Rentals in the Gwynn AreaView all 23 rentals
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    sunset cottage1 / 16
    (3)Excellent
    Gwynn
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    The following rentals are within 15 miles of Gwynn.
    Leisure Cove1 / 13
    (2)Excellent
    Kilmarnock
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    My Pan-O-Sea-A  on the Chesapeake Bay.1 / 39
    (14)Very good
    White Stone
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Rigby Retreat on the Chesapeake Bay1 / 18
    (3)Excellent
    Diggs
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Outdoor Dining Area
    • Washer
    • Porch
    • Parking
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 22, 2018
    This was a great find. We had water access, air conditioning, full working kitchen, nice locals close by. We were very blessed to have stayed here. Matthews is a cute little...
    Reviewed June 25, 2018
    Beat the touristy resort places and have a quiet getaway with your family. This place was clean, quiet, and beautiful. A cozy cottage, three bedrooms with nice kitchen and...
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    About this property
    Spend your vacation at Rigby Retreat and enjoy the best overall options! This.3 bedroom, 1 bath cottage on the Chesapeake Bay is accessed via historic Old House Woods Rd, featured in 'Ghosts of Virginia'. Fully equipped eat-in kitchen, dining room, den, screened front porch, rear deck overlooking...
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    Diggs, Virginia 23045
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Seahaven1 / 14
    (3)Excellent
    White Stone
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 29, 2017
    Everyone in my party was hesitant when I wanted to book this property. When we arrived, everyone was shocked at how comfortable and relaxing the property was.We had a great time...
    Reviewed July 26, 2016
    Seahaven was a wonderful getaway for my family. We enjoy every moment: crabbing, relaxing on the beach and outdoor games. The house had everything we needed to cook meals and...
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    About this property
    Secluded location on a seven acre point of land with 1000' of sandy beach plus boat dock. Enjoy bay breezes as you relax in a hammock or Adirondack chairs under the shade trees. Dine alfresco on the large screened porch with dining table or picnic table as you enjoy the commanding view of the...
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    Location Information
    White Stone, Virginia 22578
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Historic River Cottage at Glebefield1 / 15
    (4)Excellent
    Ware Neck
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Porch
    • Grill
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 2018
    We rented this cottage for our honeymoon. It has a rustic charm that made us feel at home. This cottage is equipped with everything you could need. There are potential...
    Reviewed November 19, 2017
    The historic cottage at Glebefield--it is amazing! Beautifully renovated yet so much of the authentic history of the old cottage has been preserved. Hand hewn beams, the old...
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    About this property
    Come and spend your vacation in this quiet, peaceful setting on the Ware River. The estate boasts 290 ft of shoreline. This charming and historic 2 story cottage sits on 7 acres located on the Ware Neck Peninsula. The cottage has hand hewn post and beam constuction dating to approximately 1790....
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    Location Information
    Ware Neck, Virginia 23061
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Little Bay Waterfront Home with Private Beach1 / 4
    (2)Very good
    White Stone
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Private Yard
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 16, 2018
    The beach (only a few steps from the yard!) was better than we could have imagined! The water was gentle and perfect temperature. The home was comfortable and very well...
    Reviewed July 10, 2014
    The rental was very comfortable and relaxing. The space was very adequate for our group. The enclosed porch is a great place to enjoy the area. However, the best part is the...
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    About this property
    Sandy beach where you can watch the ships on the Chesapeake Bay is at your own back yard. This one-level home offers 3 bedrooms, and two full baths. The living room and dining area face the Bay, and there is a fully equipped kitchen and laundry for your use. Relax in the sun room facing the...
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    Location Information
    White Stone, Virginia 22578
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Secluded Waterfront Home1 / 6
    (2)Very good
    White Stone
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Porch
    • Waterfront
    • Washer
    • Air Conditioning
    • Private Yard
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 2017
    The location was great. Outside space and Sun porch were very nice. There were not 3 baths as described. When we got there the key was not there as instructed. I called and...
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    About this property
    Located on a point of land with water on three sides, this nearly new home has 3 bedrooms, 2 full baths and can sleep 9 people. There's even a crib for a little one. The soaring ceiling in the great room provides a loft area with a window overlooking Antipoison Creek. There's a fully equipped...
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    Location Information
    White Stone, Virginia 22578
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Mobjack Bay Cottage Overlooking East River & Mobjack Bay1 / 13
    (1)Excellent
    Foster
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 24, 2014
    This cottage was comfortable, modern and clean. We spent our 13th anniversary here and couldn't be a better choice.  Peacefully,  quite, secluded, and best all we felt welcome...
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    About this property
    Cottage, 3 Bedrooms + Convertible bed(s), 2.5 Baths, (Sleeps 6) Location: Mathews, Virginia, USA (centrally located on Virginia’s Middle Peninsula between Virginia Beach and Washington DC). Mathews is a great base for exploring tidewater Virginia --- history, attractions, nature. Mathews...
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    Location Information
    Foster, Virginia 23056
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    White Stone
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Waterfront
    • Central Heating
    • Washer
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront property perfect for family vacations or a quiet romantic getaway. Located on the Rappahannock a short distance from the Chesapeake Bay. Explore local towns, great food, live music and shopping or just chill and enjoy privacy and incredible views. Wildlife sightings daily: Bald eagles,...
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    Location Information
    White Stone, Virginia 22578
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    Waterfront on Rappahannock River1 / 6
    (1)Very good
    White Stone
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Yard
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 14, 2017
    The folks at Chesapeake Properties are very nice to work with. Having access to this property allowed me and my kids and grandkids to have time with our extended family who...
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    About this property
    Family vacations are great in this 4 bedroom home on the Rappahannock River at Mosquito Point. Each bedroom has a vanity sink in the room, plus there are 2 full baths. The living room has expansive views of the river, and cable TV. The fully equipped kitchen has a large table for family dining....
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    Location Information
    White Stone, Virginia 22578
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Charm and Privacy! No Cleaning Fee! Walk to Tides Inn and Downtown Irvington!1 / 18
    (2)Excellent
    Irvington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Parking
    • DVD Player
    • Washer
    • Wi-Fi
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 17, 2016
    This house is very clean, and the yard well groomed. The neighborhood is very quiet, with people walking, who pleasantly greet you in passing. Parking is about 8 or 9 steps from...
    Reviewed May 13, 2016
    The home was very lovely and accommodating for my 2 parents, friend and myself. The large master bedroom is very roomy and on the 1st floor. The bath is updated with a large tub...
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    About this property
    Come unwind and relax at this jewel box of a house in the heart of Irvington, VA! This lovely and stylish home is the perfect place for a romantic getaway, a quiet retreat, a great place to chill after a bike ride or a day of kayaking or golfing. Conveniently located walking distance to almost...
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    Location Information
    Irvington, Virginia 22480
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Pop Castle- Historic Gem on the Rappahannock River1 / 35
    (2)Excellent
    White Stone
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Waterfront
    • Washer
    • DVD Player
    • Patio
    • Grill
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 19, 2014
    My family of four has just returned from a spring break trip to Pop Castle. We had our two children plus 5 of their friends...7 teenagers in all, and we could have fit more, as...
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    About this property
    'Pop Castle' is a magnificent estate on the Rappahannock River, one mile from the Chesapeake Bay. It is a property entrenched in civil war history, listed on the National Registry of Historic Homes and a registered Virginia Historic Landmark. This 1855 house, flanked by two majestic Oak trees...
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    Location Information
    White Stone, Virginia 22578
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    Kilmarnock
    6 Bedrooms, 2 Bathrooms, Sleeps 17 Quick View
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    Amenities & Details
    • Private Yard
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Serene, spacious getaway home on 15 acres surrounded by the Chesapeake Bay. Incredible views, deep water fishing/crabbing pier, screen porch, sun room. Great for families, romantic couples, large gatherings or personal retreats. Six bedrooms: 1) King, 2) Queen, 3) Queen + twin, 4) Double, 5)...
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    Location Information
    Kilmarnock, Virginia 22482
    Rental Home - 6 Bedrooms, 2 Bathrooms, Sleeps 17
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    White Stone
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    • Housekeeping Included
    • Grill
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront home has dock and a deck overlooking the water. There is a table and propane grill on the deck for cooking out. Comfortably furnished three bedrooms plus a bonus room that has a crib and sofa. The kitchen is fully equipped with most small appliances and there is a breakfast room...
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    Location Information
    White Stone, Virginia 22578
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    The Love Shack-A Private Beachfront Home on the Chesapeake Bay1 / 12
    (10)Excellent
    White Stone
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Ocean Views
    • Air Conditioning
    • Porch
    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 24, 2018
    Awesome rental! Especially for a family with two small kids. The house is super well appointed....made some epic meals and didn't need to bring any kitchen stuff. Grocery 15...
    Reviewed September 19, 2017
    We were looking for a quiet and scenic get-away on the beach with the added bonus of kayaks, paddle board and beach toys ...and we found the Love Shack! This was the Perfect...
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    About this property
    Love Shack is a romantic getaway or a perfect small family vacation ! This private beachfront home that is right on the Chesapeake Bay in White Stone, Virginia. You will love the sandy beach just steps away and we provide all the watersports toys and beach chairs and umbrellas. The shallow...
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    Location Information
    White Stone, Virginia 22578
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Topping
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Washer
    • Parking
    • Private Yard
    • Air Conditioning
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful beach house is located directly on the Rappahannock River with a private beach as well as a private dock - all part of the property. If you like the sun, beach, water, boating, fishing, or just sitting on the porch in the swing reading or sleeping - this house is for you. The house...
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    Location Information
    Topping, Virginia 23169
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    White Stone
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Ocean Views
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Retreat to the gorgeous Virginia coast by staying in ‘My Sweet Escape,' a 2-bedroom, 1-bath vacation rental cottage in White Stone! This vibrant property with a private beach steps away has comfortable accommodations to host 6 people and boasts amazing outdoor accommodations, including a private...
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    Location Information
    White Stone, Virginia 22578
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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