Photo by Rachael Redford

Diggs Holiday Rentals

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Holiday Rentals in Diggs

Private 5-acre Waterfront Peninsula with Beach
9.4 out of 10, Exceptional, (32)
"There were so many things to do at this beautiful location! We enjoyed boating, swimming, crabbing, disc golf, bonfires, games, and more! The house comfortably sleeps 21 people! It’s a lovely house that has an incredible view and it’s so quiet and relaxing. "
The price is AU$1,247
includes taxes & fees
1 Oct - 2 Oct
Private 5-acre Waterfront Peninsula with Beach
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
10.0 out of 10, Exceptional, (76)
"I would stay again. I didnt care for the lake of not telling you your address of location etc until few days before because we were planning a road trip with stops on way and wanted to put address in gps but I understand why they have to do ot so if your a big time planner just keep that in mind. The house itself and location and cleanliness was top notch"
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Cottage on a Private Island in the York River
10.0 out of 10, Exceptional, (312)
"The property is in a great location with stunning views. The hosts were super friendly, communcaitive and knowledge of the local area. We were able to go fishing on their nice pier. Super accomadating and pet friendly. THANKS"
Cottage on a Private Island in the York River
Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg
10.0 out of 10, Exceptional, (132)
"This was our second stay at this amazingly peaceful property. My favorite feature is the surround windows in the master bedroom, being able to have the fresh air and sounds of the water at night. Had everything we could possibly need. Thank you Shannon for being an excellent host! "
Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg
Sisters 3 by the Sea, 400 Feet To The Beach
9.4 out of 10, Exceptional, (145)
"This was our 2nd annual vacation at Sisters 3. The property has a few quirks (no back exit, dishwasher in the room next to the kitchen) but nothing that gets in the way of an enjoyable, multi generation vacation. The hosts kindly provide linens,towels, toilet paper, and a few cleaning supplies. And yes,a bottle of wine! Its just 2 blocks to the beach and the view is gorgeous. During our stay, the town had a water main break, and the hists went above & beyond to ensure we were informed. Thanks...
Sisters 3 by the Sea, 400 Feet To The Beach
The Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!
9.8 out of 10, Exceptional, (141)
"The property was great! Just what we expected! Perfect for a weekend getaway! "
The Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!
Welcome to this Waterfront Home with Amazing Views
10.0 out of 10, Exceptional, (17)
"Very nice home. Beautiful dock. Great location. Very clean."
The price is AU$570
includes taxes & fees
25 Sept - 26 Sept
Welcome to this Waterfront Home with Amazing Views
Radiant Gloucester House w/ Private Porch!
9.4 out of 10, Exceptional, (13)
"Beautifully restored interior. Air conditioning worked great. Quiet street but only steps to Main Street. Especially good for visiting residents at Riverside Sanders which is just a block away."
Radiant Gloucester House w/ Private Porch!
Waterfront Cottage with Private Beach, Sunsets over Water-FALL DATES STILL OPEN!
10.0 out of 10, Exceptional, (189)
"The cottage was a prefect size for two guests and lots of room outside. Was truly as advertised! Enjoyed watching terns and osprey fish close by. Nicely furnished and equipped and well kept. Will definitely consider going again. "
Waterfront Cottage with Private Beach, Sunsets over Water-FALL DATES STILL OPEN!
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
9.8 out of 10, Exceptional, (153)
"We really enjoyed our stay at the Little Blue House. The location could not have been better -- in walking distance to the Tides Inn, the Local, and a few cute shops. There was more to see and do just a short drive away. The house itself was very cute and my daughter loved having her own room and bathroom. The streaming options (Netflix, Hulu, etc.) didn't work, but I think they just need to be upgraded. The jacuzzi jets in the big tub were TO DIE FOR. We highly recommend!"
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
Oceanfront White Stone Cottage w/ Private Beach!
7.4 out of 10, Good, (66)
"Perfect vaca!! Just what we were looking for. Cute little quaint cottage. Peaceful, quiet, beautiful. Fantastic views, beach and susurrounding little townstowns."
Oceanfront White Stone Cottage w/ Private Beach!
Historic Cottage on Ware River Estate
10.0 out of 10, Exceptional, (250)
"Nice and peaceful cottage! Found everything we needed and more. Thank you for hosting us. "
Historic Cottage on Ware River Estate
Vacation Getaway on Chesapeake Bay
10.0 out of 10, Exceptional, (151)
"This house is truly in a perfect special spot. Super close to a few good spots to eat, and so jam packed with nature. So much nicer in person than even advertised in the pictures. Frank and Sandy couldn’t have been easier to deal with and the house was great. Kids enjoyed the heck out of the creek. Would love to visit again. "
Vacation Getaway on Chesapeake Bay
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!
10.0 out of 10, Exceptional, (142)
"The cottage was great for the two of us. Very quiet and relaxing. You can't really relax on the beach though because when the tide comes in it disappears. We went to Haven Beach to relax and swim - just a short drive away. But you can sit by the fire pit and enjoy the serene scene with jumping fish and herons. The cottage was well equipped with almost everything we needed for our stay. The tennis court was unusable - the picture does not reflect its current condition. The pool looks nice but we...
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!
Restored 1920's Cottage on 1 Acre w/ Fire Pit
9.4 out of 10, Exceptional, (50)
"The property is very beautiful. I would not say it has a river view, but it is very shaded and pretty. The house serves basic needs. Clean and comfortable beds. Clean, functioning bathroom. We used this as home-base while visiting son, DIL and grandson for his 1st birthday. "
Restored 1920's Cottage on 1 Acre w/ Fire Pit
Beach, beach, beach in historic Cape Charles. Lovely 2BR Apt1Block from beach
9.8 out of 10, Exceptional, (24)
"My daughter was married at Mimosa Barn and my husband and I (from Mass) stayed at the Beach Retreat. It was better than the what the photos portrayed and was perfect for two people (plus my daughter the night before the wedding). The owner was very gracious and we will definitely stay there again if it's available. "
Beach, beach, beach in historic Cape Charles. Lovely 2BR Apt1Block from beach
Relaxing Riverfront Cottage w/ Boat Dock!
9.8 out of 10, Exceptional, (26)
"My sister and I, both in our 60s, spent a few days in this cottage as part of our yearly Sister Vacation tradition. We had such a nice time! Upon entering the cottage, the first thing you notice is how exceptionally clean it is. It smelled amazing and was spotless. The amenities included are top-notch. Towels were plentiful, and the linens and super comfortable beds made for very peaceful sleep. We utilized the kayaks (life vests also provided). The setting is so peaceful beautiful. It's a very...
Relaxing Riverfront Cottage w/ Boat Dock!
Perfect Cozy Vacation Rental on the Eastern Shore
8.2 out of 10, Very good, (23)
"The entrance right into the bed, a mere foot from the door with the mop and cleaning supplies to the right of the door did not give a great first welcoming. The smells indicated either mustiness or seafood in the fridge or both.Yes there were air freshener candles but, deep cleaning may be best to get to the root of it. The WiFi was not correct-the links that popped up were not in sync w/what was in the binder of info. When reached out to property manager for both entry inquiry and wifi, he was...
Perfect Cozy Vacation Rental on the Eastern Shore
Cozy cottage on the Chesapeake Bay
10.0 out of 10, Exceptional, (32)
"Very peaceful. Pretty easy to find. Great views. Very much would stay again. Very good communication with owner prior to arrival. All questions answered promptly. Overall a great three day weekend spot"
Cozy cottage on the Chesapeake Bay
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
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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, (538)
"Hotel seems to be getting patched up. They need to replace the elevator almost got stuck… the breakfast area was great. The poor woman working it we felt bad because kids dropped plates of food on the floor. Checkin and check out was great. Our room looked like it was recently updated"
The price is AU$158
includes taxes & fees
22 Sept - 23 Sept
Holiday Inn Express Gloucester, an IHG Hotel
Private 5-acre Waterfront Peninsula with Beach
9.4 out of 10, Exceptional, (32)
"There were so many things to do at this beautiful location! We enjoyed boating, swimming, crabbing, disc golf, bonfires, games, and more! The house comfortably sleeps 21 people! It’s a lovely house that has an incredible view and it’s so quiet and relaxing. "
The price is AU$1,247
includes taxes & fees
1 Oct - 2 Oct
Private 5-acre Waterfront Peninsula with Beach
The Tides Inn
4.0 star property
8.8 out of 10, Excellent, (146)
"RESTAURANT and overall classy operation"
The price is AU$648
includes taxes & fees
24 Sept - 25 Sept
The Tides Inn
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.

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?

Private 5-acre Waterfront Peninsula with Beach: This holiday home rental outside of Diggs is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.