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Diggs Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Diggs vacation rentals

A forest trail with a clear path, surrounded by tall trees and dense underbrush.

1. Campsite #4 At Blanchard Farm

Campsite #4 At Blanchard Farm
Diggs
$30 nightly
The price is $33
Nov 19 - Nov 20
Total with taxes and fees
Campsite #4 At Blanchard Farm
A forest trail with a clear path, surrounded by tall trees and dense underbrush.

2. Campsite #3 At Blanchard Farm

Campsite #3 At Blanchard Farm
Diggs
$30 nightly
The price is $33
Nov 10 - Nov 11
Total with taxes and fees
Campsite #3 At Blanchard Farm
A modern kitchen with white cabinets, stainless steel appliances, a double sink, and a large window.

3. 1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town

1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town
Mathews
10.0 out of 10, Exceptional, (43 reviews)
"We had a great time at Baydreamin'."
United States
Crystal D.
$284 nightly
The price is $313
Nov 16 - Nov 17
Total with taxes and fees
1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town
A front door with a wreath, a wooden porch, and a gravel pathway.

4. Bay Dream Believer Cottage on Beautiful East River Waterfront

Bay Dream Believer Cottage on Beautiful East River Waterfront
Mathews
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful location, host communicated well"
United States
Nicole K.
$400 nightly
The price is $441
Nov 10 - Nov 11
Total with taxes and fees
Bay Dream Believer Cottage on Beautiful East River Waterfront
A small, single-story house with a porch, a wooden deck, and a brick pathway.

5. Deltaville 2BR Retreat, Walk to Museum, Boat Parking

Deltaville 2BR Retreat, Walk to Museum, Boat Parking
Deltaville
10.0 out of 10, Exceptional, (75 reviews)
"Everything was perfect - loved staying here. "
United States
John L.
Deltaville 2BR Retreat, Walk to Museum, Boat Parking
A kitchen with dark blue cabinets, a gas stove, a sink, and a window overlooking the backyard.

6. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
Gloucester
9.4 out of 10, Exceptional, (35 reviews)
"We loved the 1920’s feeling to the home. The cleanliness and quiet location were exactly what we were looking for. We were just a block from the historical center and took advantage of the shops and eateries. We would definitely stay here afain"
United States
David
$303 nightly
The price is $337
Nov 10 - Nov 11
Total with taxes and fees
Radiant Gloucester House w/ Private Porch!
A wooden deck with a white fence and a lounge chair, overlooking a calm body of water during sunset.

7. Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
9.2 out of 10, Wonderful, (27 reviews)
"Peaceful and quiet with amazing views!"
United States
Eileen D.
$352 nightly
The price is $411
Nov 10 - Nov 11
Total with taxes and fees
Smith Beach cottage w/ private sunset
A spacious living room with a large gray sectional sofa, a wooden coffee table, and a ceiling fan. There are nautical decorations on the wall and a view of a lake through large glass doors.

8. Riverfront Cottage: Fire Pit & Kayaks

Riverfront Cottage: Fire Pit & Kayaks
Deltaville
9.8 out of 10, Exceptional, (52 reviews)
"This place was a perfect getaway. Quiet and a beautiful view!"
United States
David P.
$348 nightly
The price is $384
Nov 23 - Nov 24
Total with taxes and fees
Riverfront Cottage: Fire Pit & Kayaks
A covered outdoor area with a pool, wicker furniture, and large windows offering a view of the outdoors.

9. The Bungalow, Pool, Dock, Kayaks, & Game Room

The Bungalow, Pool, Dock, Kayaks, & Game Room
Topping
$295 nightly
The price is $325
Nov 10 - Nov 11
Total with taxes and fees
The Bungalow, Pool, Dock, Kayaks, & Game Room
A covered porch with wooden benches and chairs, large windows, and a view of a grassy area.

10. Restored 1930s Cottage on 1 Acre w/ Fire Pit

Restored 1930s Cottage on 1 Acre w/ Fire Pit
Hayes
9.6 out of 10, Exceptional, (97 reviews)
"Our family of 6 (age range 20’s to 80’s) enjoyed all of the rooms and porches. The air conditioners kept the home comfortable and the porches were cozy for those who like it warmer. We liked the convenience of being able to make our own breakfasts and dinners here. Having a grill was a bonus."
United States
Susan C.
$305 nightly
The price is $339
Nov 10 - Nov 11
Total with taxes and fees
Restored 1930s Cottage on 1 Acre w/ Fire Pit
A covered porch with wicker furniture, a glass coffee table, and a view of the neighborhood.

11. Cape Haven - Condo 1.5 Blocks from Beach

Cape Haven - Condo 1.5 Blocks from Beach
Historic Downtown Cape Charles
9.8 out of 10, Exceptional, (51 reviews)
"Was wonderful..so close to everything..property was great ..had everything you need"
United States
Donna L.
$397 nightly
The price is $449
Nov 12 - Nov 13
Total with taxes and fees
Cape Haven - Condo 1.5 Blocks from Beach
A living room with a light blue wall, a wooden coffee table, a beige sofa with blue cushions, a wicker chair, and a patterned rug.

12. Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex

Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex
Historic Downtown Cape Charles
9.8 out of 10, Exceptional, (66 reviews)
"Great house perfect for our family very conveniently located!"
United States
Dorothy A.
$437 nightly
The price is $494
Nov 17 - Nov 18
Total with taxes and fees
Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex
A covered patio with a wooden ceiling, a table with chairs, and a view of a backyard with a grill and greenery.

13. Golf cart included! 5 blocks to the beach, and in historic district!

Golf cart included! 5 blocks to the beach, and in historic district!
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (17 reviews)
"The home was perfectly situated in Cape Charles and on a quiet street. The home was well equipped with everything, the kitchen was well stocked with all the cooking pots/pans and anything you needed to cook with. Check out was a breeze! The screened in porch was perfect in the evening. Golf cart is always a nice touch for properties in Cape Charles."
United States
Lori G.
$424 nightly
The price is $481
Nov 11 - Nov 12
Total with taxes and fees
Golf cart included! 5 blocks to the beach, and in historic district!
A kitchen with dark blue cabinets, a gas stove, a sink, and a window overlooking the backyard.

14. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
3.0 star property
Gloucester
$322 nightly
The price is $358
Nov 10 - Nov 11
Total with taxes and fees
Radiant Gloucester House w/ Private Porch!
A wooden deck with a chair, a welcome mat, and a view of a forest.

15. The Waverly Tree House

The Waverly Tree House
Machipongo
10.0 out of 10, Exceptional, (3 reviews)
"Very comfortable and clean spot. Great quiet morning views of the creak. We enjoyed a relaxing stay. It had everything we needed. "
United States
Jeanna C.
$274 nightly
The price is $305
Nov 10 - Nov 11
Total with taxes and fees
The Waverly Tree House
A living room with a brick wall, a sofa, a coffee table, and a painting.

16. Oyster Oasis, Modern Loft in Historic Downtown

Oyster Oasis, Modern Loft in Historic Downtown
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (16 reviews)
"First time in Cape Charles! Our stay was perfect, great location and wonderful amenities!!"
United States
Julia G.
$354 nightly
The price is $401
Nov 22 - Nov 23
Total with taxes and fees
Oyster Oasis, Modern Loft in Historic Downtown
A covered deck with wooden chairs and tables, overlooking a marina with boats.

17. The Captain's Quarters located in Cape Charles, VA offers breathtaking views.

The Captain's Quarters located in Cape Charles, VA offers breathtaking views.
Cape Charles
9.8 out of 10, Exceptional, (84 reviews)
"Very nice views of the water. Great location, close to town and restaurants."
United States
Bart
$291 nightly
The price is $331
Nov 10 - Nov 11
Total with taxes and fees
The Captain's Quarters located in Cape Charles, VA offers breathtaking views.
A dining area with a long table, chairs, a candle centerpiece, and a staircase with a railing.

18. Walk to Dining, Beach & Park~Family Friendly Home!

Walk to Dining, Beach & Park~Family Friendly Home!
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (9 reviews)
"The close proximity to the park was perfect for our children and walking our dog"
United States
Jeff
$265 nightly
The price is $302
Nov 11 - Nov 12
Total with taxes and fees
Walk to Dining, Beach & Park~Family Friendly Home!
A two-story house with a wrap-around porch, a chimney, and a flag.

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

Bay cottage, Beach 100 yards away! RESERVE NOW!!!
Historic Downtown Cape Charles
9.6 out of 10, Exceptional, (153 reviews)
"Great property and location. Loved easy walk to down town and the beach. Spent lots of time on front porch."
United States
John T.
$428 nightly
The price is $485
Nov 10 - Nov 11
Total with taxes and fees
Bay cottage, Beach 100 yards away! RESERVE NOW!!!
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.
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Top Diggs Hotel Reviews

A hotel lobby with a reception desk, chairs, a fruit bowl, framed pictures, and a waste bin.
Hampton Inn Gloucester

Hampton Inn Gloucester

Hampton Inn Gloucester
Gloucester

10/10 Excellent

Fantastic
United States
Joseph
Reviewed July 31, 2025
Hampton Inn Gloucester

Find out more about Diggs

Everything you need to know about Diggs vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Diggs vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Diggs vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Diggs vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Diggs. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Diggs in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $33 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Diggs rentals

At Expedia, we put the best Diggs vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Diggs rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Diggs vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Diggs. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Diggs?

Yes, we have vacation rentals near the most popular local attractions in Diggs, or you can select a secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Diggs?

The Crows Nest.
Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!: This vacation home rental outside of Diggs is located on the waterfront and offers a balcony, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

What can I see and do in Diggs?

Chesapeake Bay and Bethel Beach are a couple of lovely local spots to get outside and enjoy nature. Bethel Beach Natural Area Preserve and Gwynn's Island Museum are a couple of places you'll find in the larger area.

What are vacation rentals like in Diggs?

Vacation rentals are privately owned accommodations you can reserve for a few days or a quick weekend in Diggs. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family trip.

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