Book Holiday Homes in Centreville

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Centreville

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Annapolis
A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

stevensville
Located in Stevensville, this vacation home is on the waterfront, a 1-minute drive from Love Point State Park and 7 minutes from Paul Reed Smith Guitars.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Stevensville
The price is AU$425 per night from 28 Apr to 29 Apr
AU$425
includes taxes & fees
28 Apr - 29 Apr
Located in Stevensville, this vacation home is a 4-minute drive from Matapeake State Park and 7 minutes from Paul Reed Smith Guitars.
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Save an average of 15% on thousands of hotels when you're signed in
Historic Annapolis Home 1.5 blocks from center of town.

Historic Annapolis Home 1.5 blocks from center of town.

Annapolis
A stay at this vacation home places you in the heart of Annapolis, within a 15-minute walk of U.S. Naval Academy and Spa Creek.
Historic Annapolis Home 1.5 blocks from center of town.
Waterfront w/upper sundeck and private pier located near Rock Hall,  sleeps 18.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Muskrat Park.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2 out of 5
Annapolis
With a stay at this vacation home in Annapolis (Oyster Harbor), you'll be within a 15-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping ...
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Steps to USNA Gate 3 at historic Gatehouse, on-site parking

Steps to USNA Gate 3 at historic Gatehouse, on-site parking

2.5 out of 5
Annapolis
Steps to USNA Gate 3 at historic Gatehouse, on-site parking is in the heart of Annapolis, within a 5-minute walk of St. John's College and U.S. Naval ...
Steps to USNA Gate 3 at historic Gatehouse, on-site parking
PERFECT LOCATION in the heart of history

PERFECT LOCATION in the heart of history

Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, steps from U.S. Naval Academy and John Smith House.
PERFECT LOCATION in the heart of history
Don't see what you're looking for?
See all available properties in Centreville
View all properties
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.

Centreville Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Centreville vacation homes are the perfect way for you to wing it.

Holiday houses in Centreville let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Centreville in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Centreville adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Centreville with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Centreville vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Centreville Holiday Homes essential information

Accommodation
595 Holiday Homes
Lowest Price
AU$225
Highest Price
AU$425
Popular accommodation
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , 240' Private Beachfront @Kent Island Love Point - Great for Large Groups, ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Historic Annapolis Home 1.5 blocks from center of town., Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18., Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks, Steps to USNA Gate 3 at historic Gatehouse, on-site parking, PERFECT LOCATION in the heart of history

Top trending hotels in Centreville

Waterfront family resort Lodge with private pier, game room and bar

Waterfront family resort Lodge with private pier, game room and bar

Centreville
Located in Centreville, this vacation home is on a river, within a 10-minute drive of Hazel Miner Monument and Earle Landing.
Waterfront family resort Lodge with private pier, game room and bar
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$312 per night from 4 May to 5 May
AU$312
includes taxes & fees
4 May - 5 May
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Historic Inns of Annapolis
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$267 per night from 27 Apr to 28 Apr
AU$267
includes taxes & fees
27 Apr - 28 Apr
With a stay at The Westin Annapolis in Annapolis, you'll be in the historical district, within a 5-minute drive of U.S. Naval Academy and People's Brewer Hill ...
The Westin Annapolis
Save an average of 15% on thousands of hotels when you're signed in
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 27 Apr to 28 Apr
AU$225
includes taxes & fees
27 Apr - 28 Apr
Located in Grasonville, Hyatt Place Kent Narrows & Marina is in the historical district, a 2-minute drive from Chesapeake Exploration Center and 7 minutes from ...
Hyatt Place Kent Narrows & Marina
Don't see what you're looking for?
See all available properties in Centreville
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.