
Vacation rentals in Diggs
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Top-rated vacation rentals in Diggs
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Guest favorite

Home in Gloucester
4.94 out of 5 average rating, 88 reviewsCharming Cottage Historic Gloucester Main Street
KatyRating, 5 stars2 weeks ago
the cottage was beautiful and I had one small issue and it was resolved very quickly. I stayed there because my daughter lives there in Gloucester and we celebrated my 75th birthday. All in all it was a wonderful week!!!!!
Guest favorite

Home in Port Haywood
4.93 out of 5 average rating, 15 reviewsEast River/Mobjack Bay Mathews
AmandaRating, 5 stars2 weeks ago
We enjoyed our stay & really enjoyed being on the water. The dock was lovely to fish off of, there was plenty of yard space for our kids to run around & get energy out. Beds were comfortable. Was a really great stay & we will probably try to book again in the future!
Top guest favorite

Guesthouse in Mathews
4.96 out of 5 average rating, 46 reviewsMagnolia Cove waterfront 1BR upper cottage
BethRating, 5 stars3 weeks ago
Stayed in Meredith's above-garage apartment while in Mathew's for the Tour de Chesapeake bike ride. The apartment was clean and comfortable and easy to access with lots of little extras - snacks, water bottles, gym and access to laundry. Took advantage of the kayaks almost as soon as I arrived. The apartment was well stocked with thoughtful extras. A nice touch I always appreciate - well-placed, sturdy hooks in the bathroom, make it easy to hang toilet kit and keep clothes off the ground. The place was private, clean and extremely comfortable and Meredith was super easy to communicate with.
Top guest favorite

Place to stay in Machipongo
5 out of 5 average rating, 74 reviewsSmokehouse on the Chesapeake Bay
NatalieRating, 5 stars2 weeks ago
Kenneth was an exceptional host for the following reasons -provided great recommendations for food, adventure on & off the property, & everything in between -approachable when we had questions and/or curiosity -clear & prompt communication -such a cozy, welcoming restored smokehouse (smelled like cedar, oak, & pine in there..LOVED it) -very well kept & clean, his & her robes were perfect for the shower & towels, washcloths, & linens were ready & waiting - fully stocked with treats, coffees & teas -gorgeous property w/ amazing dock for casting a few & enjoying unreal sunsets - super peaceful & serene My husband & I had our mini moon here & it was a continuation of our dreamy marriage to each other. We look forward to our return <3 Love, The Sassers
Guest favorite

Cottage in Gwynn
4.86 out of 5 average rating, 36 reviewsSunset Haven
ConnieRating, 5 stars7 months ago
This is our second time staying at Sunset Haven— appropriately named. Gorgeous sunsets and weather was perfect. Great and considerate communication with Terri. House was pristine and had every thing you could need. We will be back! Thank you Terri!

Farm stay in Cardinal
4.9 out of 5 average rating, 165 reviewsWtrfrnt aptmnt w/pool/dock on private farm
Diane At HOARating, 5 stars5 days ago
Wonderful experience, nice amenities on private location that included an in ground pool, water access with canoe and kayaks and barn yard critters (goats, chickens and sheep dogs). Such a peaceful setting and gracious hosts.
Guest favorite

Home in Gwynn
5 out of 5 average rating, 31 reviewsIsland Oasis 4+ acre waterfront house with hot tub
ElaineRating, 5 stars1 week ago
Stephanie’s bay house is a true island oasis. This was our second stay, and it certainly won’t be our last. The home is beautiful, and the setting is nothing short of breathtaking. Peaceful, warm, and incredibly family-friendly, it’s the perfect place to unwind and connect. We especially enjoyed the kayaks, evening conversations on the screened-in porch while watching the sunset, and sharing meals around the large dining table outdoors. Every visit leaves us with cherished family memories that we’ll treasure for years to come.
Top guest favorite

Guest suite in Gloucester
5 out of 5 average rating, 17 reviewsCarriage House
KaileyRating, 5 stars1 month ago
Our stay was wonderful. The place was clean, comfortable, and easy to find. Richard and Sue were amazing hosts and we’d stay here again next time we visit!
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