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Compare 471 Vacation Homes in Centreville with updated reviews, rates, and availability.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

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

10.0 out of 10, Exceptional, (206)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

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

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Freshly renovated 3-story home 1 block from USNA!

10.0 out of 10, Exceptional, (29)
"Best property we’ve stayed at in Annapolis by far. We look forward to our next stay. The property was spacious, well stocked, cozy and full of beautiful light! Central location to everything you need. Friendly neighborhood and great location. "
The price is SAR 555
SAR 2,391 total
includes taxes & fees
4 Feb - 5 Feb
Freshly renovated 3-story home 1 block from USNA!

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

10.0 out of 10, Exceptional, (73)
"Heron house was perfect for our family weekend getaway. Doug and Kris are great hosts and made our stay as easy as could be! "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (4)
"An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!"
Pet-Friendly Home on Chester River w/ Dock!

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (21)
"I love this property and host! Incredible place to stay close to museums the Naval Academy, local shopping, excellent restaurants and the airport. I will highly recommend this property to friends & family. "
Charming Historic Townhouse Steps From USNA

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (15)
"Everything about this property was first class! We had an amazing stay in this comfortable home! Fully stocked kitchen. Body wash and shampoo in each bathroom. All the details covered. The location is awesome. Quick walk to downtown and the Naval Academy. The host was very accommodating and responsive. Can’t wait to stay again!"
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Walk to Everything House

10.0 out of 10, Exceptional, (76)
"Nice location down town. House was just as the pictures showed. "
Walk to Everything House

Brand New Spacious Luxury Home

10.0 out of 10, Exceptional, (4)
"Property is great for families!!"
Brand New Spacious Luxury Home

Cozy 5 bedroom house with attached guest suite

Cozy 5 bedroom house with attached guest suite

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Circa 1700 Chesapeake Colonial home on the National Register.

9.8 out of 10, Exceptional, (50)
"Very cool house with great host. Very spacious. Excellent kitchen and very cozy. It would have been helpful to know about the staircases. We had an 8 month pregnant woman and 2 year old that were not able to come but it would have been an issue as getting to the single bed rooms is challenging."
Circa 1700 Chesapeake Colonial home on the National Register.

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

10.0 out of 10, Exceptional, (21)
"Convenient to restaurants and a warm, comfortable place to gather and relax after a hard, cold waterfowl hunt"
The price is SAR 256
SAR 911 total
includes taxes & fees
4 Feb - 5 Feb
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

8.8 out of 10, Excellent, (11)
"The location is spectacular with expansive views of the Chesapeake Bay and the Bay Bridge. The house itself is immaculate and had lots of space for our family. I would imagine it's even better in the summer when the pool is available.One caution: the playhouse is really cool but not a place to let younger kids play unsupervised."
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (57)
"Great location! Beautifully furnished! I stayed here for a month and loved it. The property manager is awesome. Responds to requests within minutes. Book it you won’t be disappointed!"
Recently Renovated Annapolis Home - Conveniently Located

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (33)
"The bay cottage's porch was a perfect spot to enjoy a bottle of wine and snacks provided by the thoughtful hosts. Clever decor , furnishings, and sauna made our stay special and warm. Had crab dinner viewing sunset over the bay at dockside suggested by hosts. we hope to return. "
The price is SAR 656
SAR 1,010 total
includes taxes & fees
4 Feb - 5 Feb
BAYSIDE BUNGALOW

Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

9.8 out of 10, Exceptional, (9)
"This was a perfect home away from home for four adults and two children, ages 5 and 7. The children loved the loft area and named it the "Kids Zone." The pool and the massive amount of toys were a big hit too. Lots of towels, kitchen equipment, beautiful bed linens, outdoor and indoor spaces made this a wonderful vacation home. While the waterfront was beautiful the front porch was our favorite spot in the morning, Just lovely."
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (31)
"We just finished a great three day stay at this property. The place was spotless and the location to the towns of the eastern shore was perfect. Wonderful to look out and see the river lazily roll by. The"
Stylish Home on the Choptank River (with Tidal Beach)
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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Other property types in Centreville

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

9.8 out of 10, Exceptional, (24)
"We had a great time. Place was unique and good for group get together. "
Waterfront family resort Lodge with private pier, game room and bar

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

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
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.