Wachapreague 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 Wachapreague

Virginia Retreat w/ Porch & Grill, Near Beaches!
10.0 out of 10, Exceptional, 2 reviews
"Wonderful hosts!"
Virginia Retreat w/ Porch & Grill, Near Beaches!
Virginia Retreat w/ Porch & Grill, Near Beaches!
3.0 star property
Virginia Retreat w/ Porch & Grill, Near Beaches!
Two separate Apartments
3.0 star property
Two separate Apartments
Save an average of 15% on thousands of hotels when you're signed in
Seaside Retreat
3.0 star property
Seaside Retreat
Nassawadox Creek Waterfront Home with Private Pool
10.0 out of 10, Exceptional, 31 reviews
"All girls weekend was a great success. The house was clean and comfortable. Very vintage style. The view was great."
Nassawadox Creek Waterfront Home with Private Pool
As close as you can get to the ocean south of Chincoteague
10.0 out of 10, Exceptional, 123 reviews
"The house was perfect for our family’s long weekend stay in April 2024. The location is splendid for its views, water accessibility and peace and quiet. We kayaked to the barrier island (approx.15 min) and found many pristine whelk sea shells. We thoroughly enjoyed crabbing and fishing in the creek as well bird watching. The homeowners really have provided just about everything you could ask for as far as amenities and supplies. Additionally they were very helpful and informative when we had...
The price is NZ$821
per night
16 Jun - 17 Jun
As close as you can get to the ocean south of Chincoteague
Bobtown Bungalow- By the Chesapeake Bay
10.0 out of 10, Exceptional, 1 review
Bobtown Bungalow- By the Chesapeake Bay
Holly Cove Suite has gorgeous sunsets and spectacular views of Onancock Creek.
The price is NZ$323
per night
3 Jun - 4 Jun
Holly Cove Suite has gorgeous sunsets and spectacular views of Onancock Creek.
Inviting Waterfront Cottage on Cedar Creek
10.0 out of 10, Exceptional, 25 reviews
"Three family groups - 5 adults and one toddler - lot of room so not on top of each other - we cooked in all weekend - nicely equipped kitchen, roomy dining table (also great for games and cards). Thoroughly enjoyed the porch room - beautiful view. Walked around the yard with the toddler - spacious. Used the kayaks - nice to have that option. Took some walks - nice area. Next door neighbor - not close, but was playing loud music while setting up for a party, a minor irritant. During the party...
Inviting Waterfront Cottage on Cedar Creek
Awesome private off grid cabin with creek view.
9.4 out of 10, Exceptional, 9 reviews
"Beautiful slice of heaven on the creek. Lots of wildlife and close enough to downtown that you can have a nice night out or just light a fire and enjoy nature."
Awesome private off grid cabin with creek view.
Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK
9.4 out of 10, Exceptional, 142 reviews
"The stay was great if you don’t mind cameras watching you. Propane tank was empty, couldn’t sit on balcony because straw would go up my ass from the crappy chairs. Stove top was dirty with mysterious fluid. It was what it was. Plenty to do in area. Plenty of undersize crab available- we threw them back."
Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK
Charming Cottage - Ultimate Relaxation Destination
10.0 out of 10, Exceptional, 108 reviews
"My cousin and I stayed in the cottage for a girls' weekend. We adore it! We wish we could live here forever! It is clean and comfortable and better than the photos represent. We especially love the layout and charming decor. It is very close to the quaint little town. We enjoyed lunch on the deck at Mallard's. We had lots of fun at The Blarney Stone for karaoke. We highly recommend this cottage!"
Charming Cottage - Ultimate Relaxation Destination
Charming Painter Home w/ Chesapeake Bay Views
8.2 out of 10, Very good, 42 reviews
"Stayed here to go fishing worked out great"
Charming Painter Home w/ Chesapeake Bay Views
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks
10.0 out of 10, Exceptional, 1 review
"I knew instantly that this was the place for our group of 10! Lots of space to accommodate that many people in one area. It is a bit of a drive into Cape Charles, but it is worth it! Highly recommend this house!"
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
10.0 out of 10, Exceptional, 20 reviews
"The room was as presented. Clean and nicely appointed. Some noise from downstairs reminded us of apartment living. It would have helped to be assured that there was no way to get from ground level apartment to the upstairs apartment from inside."
The price is NZ$541
per night
5 Jun - 6 Jun
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
Calling all hunters, almost 33 more acres across the street used for hunting.
9.0 out of 10, Wonderful, 26 reviews
"The Clifton House is like stepping into your own manor by the bay. The large 5-acre property ensures privacy and peace. Upon our arrival, the home was clean and the furniture in good condition. The house is LARGE with room for everyone in our party of 8 to spread out and relax. For 6 guests in our party, this was their second stay at the Clifton House, and they all said it was as wonderful as they all remembered. All the rooms boast gorgeous views and lots of light from the numerous windows....
Calling all hunters, almost 33 more acres across the street used for hunting.
Bayfront Retreat w/ Game Room + Outdoor Pool!
9.8 out of 10, Exceptional, 23 reviews
"Beautiful location! Great for a family long weekend! We had a awesome time together!"
Bayfront Retreat w/ Game Room + Outdoor Pool!
Charming 3-bedroom house with game room in Historic Onancock. Pet friendly
10.0 out of 10, Exceptional, 1 review
"The property was very clean. Had plenty of little extra things as in coffee and snacks!! All the parking was a positive plus."
Charming 3-bedroom house with game room in Historic Onancock. Pet friendly
Secluded Seaside Village Retreat in Fishing Town
9.6 out of 10, Exceptional, 8 reviews
"We were very comfortable during our stay!"
Secluded Seaside Village Retreat in Fishing Town
This is the NO DRAMA ZONE you have been looking for! Come relax and HAVE FUN!
10.0 out of 10, Exceptional, 151 reviews
"We enjoyed a beautiful, peaceful stay, it's a return visit to the property for us, so we knew what to expect and look forward to it. Never disappointed staying here, Christi helps you feel very welcome to use and enjoy the property."
This is the NO DRAMA ZONE you have been looking for! Come relax and HAVE FUN!
Don't see what you're looking for?
See all available properties in Wachapreague
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.

Other types of properties in Wachapreague you may be interested in

Wachapreague Inn
3.0 star property
9.2 out of 10, Wonderful, 74 reviews
"I liked the friendly staff! "
The price is NZ$221
per night
10 Jun - 11 Jun
Wachapreague Inn
Virginia Retreat w/ Porch & Grill, Near Beaches!
10.0 out of 10, Exceptional, 2 reviews
"Wonderful hosts!"
Virginia Retreat w/ Porch & Grill, Near Beaches!
Virginia Retreat w/ Porch & Grill, Near Beaches!
3.0 star property
Virginia Retreat w/ Porch & Grill, Near Beaches!
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wachapreague holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wachapreague. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wachapreague. Seeing all the best attractions is bound to make you fall in love with Wachapreague. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wachapreague short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Wachapreague?

Yes, there are holiday rentals close to the most popular sights in Wachapreague, 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 Wachapreague has to offer?

Virginia Retreat w/ Porch & Grill, Near Beaches!: This highly rated holiday home rental in Wachapreague offers a fireplace, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a microwave and a coffee maker, so that you can cook with friends or family.

What can I see and do in Wachapreague?

Explore the area and family-friendly sights such as North Street Market, or get out into nature at a spot like Parramore Beach. Northampton Shopping Center and Eastern Shore Railway Museum are a couple of places you'll find in the wider area.

What are holiday rentals like in Wachapreague?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wachapreague. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for small groups.

Recent reviews of Wachapreague properties
Expedia verified reviews