Photo by Rachael Redford

Diggs Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Diggs

Cottage on a Private Island in the York River

10.0 out of 10, Exceptional, (319)
"Give yourself 24 hours to settle in. We arrived in perfect weather for a 4 day respite and only for one day, with land breezes, did we experience some pesky flies. The fresh salt air, wide star-lit skies, 24/7 quiet and mesmerizing moon-glow off the waters, 360 degrees worth, more than make up for any such small annoyance. There is some history to appreciate about the island and the cottage. When you find yourself first thing in the morning checking the tide schedules, you will then realize...
Cottage on a Private Island in the York River

Bay cottage, Beach 100 yards away! RESERVE NOW!!!

9.6 out of 10, Exceptional, (129)
"Loved everything about this lovely cottage and especially walking to the bay! Rick was extremely kind and helpful. Hope to come back!"
The price is AU$734
includes taxes & fees
1 Dec - 2 Dec
Bay cottage, Beach 100 yards away! RESERVE NOW!!!

Waterfront Cottage with Private Beach, Sunsets over Water

10.0 out of 10, Exceptional, (194)
"The house was very clean upon entering and the view was beautiful. It was conveniently located to shops and restaurants. We enjoyed visiting the nearby Hatchery while there. "
Waterfront Cottage with Private Beach, Sunsets over Water

Oceanfront White Stone Cottage w/ Private Beach!

7.4 out of 10, Good, (69)
"Just what we were looking for,great bay view ,off the beaten path"
Oceanfront White Stone Cottage w/ Private Beach!

Relaxing 1 bedroom 2019 Camper beside the Seven River

9.2 out of 10, Wonderful, (17)
" The location was great if you want a quiet place and close to the river. We enjoyed walking down to edge and watching the water. We also enjoyed walking around the neighborhood. The camper was very clean. Kimberly and her husband were very nice and helped with the few little problems that we had. We really enjoyed our stay there."
The price is AU$234
includes taxes & fees
2 Dec - 3 Dec
Relaxing 1 bedroom 2019 Camper beside the Seven River

Enjoy family fun and Sunsets at Piankatank Point.

9.8 out of 10, Exceptional, (47)
"Quiet place, loved the water view"
Enjoy family fun and Sunsets at Piankatank Point.

Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.

9.4 out of 10, Exceptional, (114)
"Excellent place to enjoy 4 generations of my family. Plenty of space to play with my grandkids outside and games to enjoy on the inside. Very quiet neighborhood and plenty of privacy."
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.

Cozy cottage on the Chesapeake Bay

9.8 out of 10, Exceptional, (37)
"The house was perfect for our weekend. Great views! The house had everything we needed. Appreciated all the extras like toilet paper, paper towels, condiments, coffee, and more. Super easy to check out. Sidenote, the only TV is in the master bedroom. Would probably be useful if the TV stand had wheels so it could be pulled into the living room for everybody to watch a movie. The house is 15 minutes away from a small winery, with tons of wine and food options and the town of Matthews, with a...
Cozy cottage on the Chesapeake Bay

Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

10.0 out of 10, Exceptional, (140)
"We didn’t want to leave. This place is heaven. Simply amazing. "
Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

The River House at Whitestone: Pet Friendly, Secluded Private Beach, w/ Kayaks!

9.6 out of 10, Exceptional, (18)
"The property is very secluded, You feel like the world is behind you. It is peaceful and quiet, The sound of nature will be the only symphony you’ll hear. I love the private beach area. We fished and caught some crab on the boat deck. The house is a bit old but that is where the charm is. There was some bug in the house but that was expected. Overall we had great time. "
The River House at Whitestone: Pet Friendly, Secluded Private Beach, w/ Kayaks!

Radiant Gloucester House w/ Private Porch!

9.6 out of 10, Exceptional, (16)
"Wonderful "
Radiant Gloucester House w/ Private Porch!

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

10.0 out of 10, Exceptional, (85)
"Great location to see the birth of our nation. House very clean and very quiet neighborhood. Appliances clean and work well stocked kitchen rules were few and simple if I had to say anything bad it would have to be the water I would bring in my drinking water "
"Bee Haven" Cottage Retreat Near Colonial Williamsburg

Welcome to this Waterfront Home with Amazing Views

10.0 out of 10, Exceptional, (18)
"Gorgeous quiet property, clean and well appointed with additional small touches to make for a lovely welcome and stay (eg coffee to get started, shower gel/soap, clocks in bedrooms, nightlights, railings for stairs into property which was really helpful having my 87yr mother with me who has some mobility challenges). Wonderful (lit) dock to enjoy, watching the world (and egrets!) go by. Fabulous local country store nearby and a great central location for exploring the area. Very responsive host....
The price is AU$594
includes taxes & fees
9 Dec - 10 Dec
Welcome to this Waterfront Home with Amazing Views

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (39)
"This is a beautiful house and Nancy is an outstanding host. We enjoyed sitting by the pool and birdwatching. My wife wanted to take the scenic main room home with us. "
Nassawadox Creek Waterfront Home with Private Pool

Vacation Getaway on Chesapeake Bay

10.0 out of 10, Exceptional, (153)
"Such a nice peaceful place. There is a short kayak paddle to the Chesapeake Bay. Lots of Kayaks to choose from too, kayaks for the novice to the expert paddler or bring your own like I did. Frank and Sandy are the hosts and could not be more accommodating. This is the best equipped Holiday home we have stayed in and we have stayed in quite a few over the years. Best of all we could bring our wonderful Dog Angus, he's not just a Pet he's family!"
Vacation Getaway on Chesapeake Bay

River Vibes@ the Piankatank River

10.0 out of 10, Exceptional, (25)
"I and some other croquet players were staying here recently for the World Golf Croquet Championships. It's only about 10 minutes from the courts, so very convenient for early morning games. The host was very responsive and the price was quite reasonable for the area and the amount of time we spent there. All of us would absolutely stay there again. "
River Vibes@ the Piankatank River

Private, 7-acre waterfront retreat on Winter Harbor Haven

10.0 out of 10, Exceptional, (122)
"Family and dog had a wonderful time at this off-the-beaten path waterfront gem. Great water access and beautiful views from the screened porch. Enjoyed crabbing, beach walks at nearby preserve, sunrises, quaint town w cute shops."
Private, 7-acre waterfront retreat on Winter Harbor Haven

Amazing views of the Chesapeake Bay.

10.0 out of 10, Exceptional, (18)
"Loved it"
Amazing views of the Chesapeake Bay.

Peaceful Waterfront Cottage on VA’s Northern Neck

10.0 out of 10, Exceptional, (93)
"We really enjoyed our stay! Would definitely rent again. "
Peaceful Waterfront Cottage on VA’s Northern Neck

Water front Oasis with pickle-ball court and hot tub

8.8 out of 10, Excellent, (5)
"We had a wonderful time staying at this home. We were a group of 12 ladies getting away for a girls weekend. This place was perfect, we did not leave for 3 days! Pickleball, paddle boarding, hot tub, and the arcade kept us busy. We were also able to go on long walks in the area. Plenty of room for everyone and a nice large kitchen to cook meals in and just hang out!"
The price is AU$2,601
includes taxes & fees
23 Dec - 24 Dec
Water front Oasis with pickle-ball court and hot tub
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.
Don't see what you're looking for?
See all available properties in Diggs
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Diggs you may be interested in

Holiday Inn Express Gloucester, an IHG Hotel

3.5 star property
7.2 out of 10, Good, (552)
"It was a nice place to stay, quiet and clean."
The price is AU$198
includes taxes & fees
27 Nov - 28 Nov
Holiday Inn Express Gloucester, an IHG Hotel

Cottage on a Private Island in the York River

10.0 out of 10, Exceptional, (319)
"Give yourself 24 hours to settle in. We arrived in perfect weather for a 4 day respite and only for one day, with land breezes, did we experience some pesky flies. The fresh salt air, wide star-lit skies, 24/7 quiet and mesmerizing moon-glow off the waters, 360 degrees worth, more than make up for any such small annoyance. There is some history to appreciate about the island and the cottage. When you find yourself first thing in the morning checking the tide schedules, you will then realize...
Cottage on a Private Island in the York River

Hampton Inn Gloucester

2.5 star property
9.2 out of 10, Wonderful, (660)
"Was relaxing and convenient!!"
The price is AU$202
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn Gloucester
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Diggs?

Yes, there are holiday rentals close to the most popular sights in Diggs, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Diggs has to offer?

Bay cottage, Beach 100 yards away! RESERVE NOW!!!: This holiday home rental outside of Diggs is located near the beach, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Diggs?

Explore the area and family-friendly sights such as Deltaville Maritime Museum, or get out into nature at a spot like Bethel Beach. Bethel Beach Natural Area Preserve and Gwynn's Island Musuem are a couple of places you'll find in the wider area.

What are holiday rentals like in Diggs?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Diggs. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great option for families.