Holiday Homes in Centreville

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Featured Holiday Homes in Centreville

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

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

10.0 out of 10, Exceptional, (202)
"Great location, great property, great communication with owner. If you stay in Annapolis, you know how stressful it is finding street parking. The included parking spot in the secure garage (directly behind the rental) was a huge bonus for this property! "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Walk to Everything House
Fridge, microwave, oven, stovetop

Walk to Everything House

10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House
Private Waterfront Woods | Dock, Kayaks, Views
Interior

Private Waterfront Woods | Dock, Kayaks, Views

10.0 out of 10, Exceptional, (14)
"Enjoyed the location and proximity to the city. Water view and firepit enjoyable. Disappointed that the dock and kayaks not easily accessible. House needs some tlc (we provided a list of easy repairs/maintenance needed.) Love to know why the ceiling fans and lights go on and off randomly."
Private Waterfront Woods | Dock, Kayaks, Views
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (12)
"We very much enjoyed our stay. The house is exactly as described and we would stay here again if we are in Annapolis again. The house has everything you need with a fully equipped kitchen, smart tvs in every room, and the beds are very comfortable. There is so much parking and the house is walking distance to everything in downtown Annapolis and the Naval Academy. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Pet-Friendly Home on Chester River w/ Dock!
Interior

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
10.0 out of 10, Exceptional, (1)
Pet-Friendly Home on Chester River w/ Dock!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (20)
"Wonderful serene location on a tributary to the Bay. Beautiful water views with its own dock and kayaks. 15 minutes to Annapolis. House is very comfortable, freshly and attractively decorated, and well stocked. Manager was extraordinarily helpful. Nine of us had a perfect relaxing long weekend. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Charming Annapolis WaterVIEW Home
Outdoor dining

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (49)
"Wonderful location to downtown Annapolis! Beautiful home, well maintained and plenty of room. The porch overlooking the bay has a table for 10 which provided a wonderful setting for our family. This is our second stay and we’ll absolutely stay again "
Charming Annapolis WaterVIEW Home
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Smart TV, books

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

10.0 out of 10, Exceptional, (22)
"The pictures dont do this rental house justice. It was very clean and wonderfully decorated. The seperate unit was ideal for my daughter and her family. The "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Fridge, microwave, stovetop, dishwasher

Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16

10.0 out of 10, Exceptional, (48)
"The house was beautiful. The location was perfect. The owner was very responsive. 5 couples stayed in the house and we would all love to return. Thank you for everything!!"
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
3 Story Stunner in Murray Hill <1 mile from USNA!
Terrace/patio

3 Story Stunner in Murray Hill <1 mile from USNA!

10.0 out of 10, Exceptional, (18)
"Very nicely renovated property in the heart of downtown Annapolis. Highly recommend for groups / families and very kid friendly. Great location to walk to all that Annapolis has to offer. "
The price is AU$1,352
includes taxes & fees
9 Dec - 10 Dec
3 Story Stunner in Murray Hill <1 mile from USNA!
Bennett House (entire):Haven in Historic Annapolis
Property grounds

Bennett House (entire):Haven in Historic Annapolis

10.0 out of 10, Exceptional, (11)
"The Bennett House not only lived up to its pictures online, the cleanliness, abundance of extra special touches, communication with the host, and more surpassed our expectations. The beds were extra comfy, the kitchen, fully stocked, the bathrooms, adorned with the fluffiest white towels and extra toiletries . . . and I can't say enough about the front porch. Even though clouds cloaked the sky when we arrived and when we left, sunshine streamed through our Annapolis trip because of the Bennett...
Bennett House (entire):Haven in Historic Annapolis
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
Outdoor dining

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

10.0 out of 10, Exceptional, (61)
"What an amazing place... the sunsets, the house, the pool, the amenities... absolutely everything was perfect! The owner was super helpful! "
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
Waterfront family resort Lodge with private pier, game room and bar
Game room

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

9.8 out of 10, Exceptional, (23)
"The property was excellent for a large group. We was there for a Sailing Regatta on the lake in front of the house. The perfect house for groups."
Waterfront family resort Lodge with private pier, game room and bar
ACROSS FROM STADIUM - walk to downtown Annapolis.
Fridge, microwave, oven, stovetop

ACROSS FROM STADIUM - walk to downtown Annapolis.

9.6 out of 10, Exceptional, (42)
"Property was great and accommodated 7 of us easily. Quiet location, close to everything for our stay in Annapolis. "
ACROSS FROM STADIUM - walk to downtown Annapolis.
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
Terrace/patio

Charming brick home with patio, WiFi, AC, & W/D - walk to everything

8.8 out of 10, Excellent, (19)
"Loved this location as EVERYTHING is walkable - St John's college, USNA, the capitol and Main Street. One skinny parking place was appreciated and reasonable for a standard size vehicle (not super truck or SUV). Enjoyed the older character of the home and modern conveniences as well as small outdoor space that was very nicely landscaped with flowers. "
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
Private pier at Waterfront Kent Island home on the Bay with Hot Tub (Open!)
Fridge, microwave, oven, stovetop

Private pier at Waterfront Kent Island home on the Bay with Hot Tub (Open!)

9.8 out of 10, Exceptional, (24)
"Despite the rainy weather from hurricane Debby, our family enjoyed our stay at this house/ property. The property was well appointed and we didn’t need for anything. We loved the porch, the dock and the water views. The house was very clean and there was plenty of space to spread out if needed. It was a peaceful getaway. Our hosts were wonderful and were easy to contact and helpful with information. "
Private pier at Waterfront Kent Island home on the Bay with Hot Tub (Open!)
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Property grounds

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!

10.0 out of 10, Exceptional, (14)
"This property was great for our group of 6 adults. Plenty of space for us to hang out, comfortable rooms and beds, the kitchen had everything we needed. Unfortunately with the weather we weren’t able to use the outside much but it was very cute and looked cozy! It is a short walk to Main Street with cute shops, a grocery store and coffee shop. We all would happily come back again! "
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Beach nearby, sun-loungers, beach towels

RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

7.4 out of 10, Good, (3)
"About a 10 minute walk to main street, 15-20 to the Marinas. The house is cute, has a nice common room, and the bed was comfy."
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
One-level waterfront home with beach and views all the way to the Bay Bridge
Smart TV

One-level waterfront home with beach and views all the way to the Bay Bridge

2.0 star property
9.6 out of 10, Exceptional, (5)
"We enjoyed our time here. The location is perfect, right on the water with beautiful sunset views. I thought the home could have some more seating space in the main living room area, but it worked well for our family of 5 (4 adults, 1 child). There was a bit of a musty smell throughout the duration of the stay, but it didn't hinder our enjoyment of the property. We'd definitely stay there again."
One-level waterfront home with beach and views all the way to the Bay Bridge
Pet-Friendly Annapolis Home: Walk to Beach!
Beach nearby

Pet-Friendly Annapolis Home: Walk to Beach!

10.0 out of 10, Exceptional, (3)
"I took my family down for the weekend to see the Navy football game. The house was perfect and as described. The outside space was just as nice as inside and the neighbors were friendly too. We will absolutely rent here again. "
Pet-Friendly Annapolis Home: Walk to 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

Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun-loungers, beach towels

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (97)
"My wife and I, and our daughter's family (including our grandkids (ages 5 and 8) spent an amazing long weekend at Spring Cove Farm. We all loved our stay so much. The house was spotlessly clean and had everything we needed and the pier/water was gorgeous with ample kayaks and paddle boards. The kids fished from the pier for hours upon hours each day, and were thrilled at the selection of toys. Our daughter and son-in-law were working remotely and the Wi-Fi and Internet worked perfectlu. Dr....
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

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

10.0 out of 10, Exceptional, (202)
"Great location, great property, great communication with owner. If you stay in Annapolis, you know how stressful it is finding street parking. The included parking spot in the secure garage (directly behind the rental) was a huge bonus for this property! "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (20)
"Wonderful serene location on a tributary to the Bay. Beautiful water views with its own dock and kayaks. 15 minutes to Annapolis. House is very comfortable, freshly and attractively decorated, and well stocked. Manager was extraordinarily helpful. Nine of us had a perfect relaxing long weekend. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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.
Beautiful view of the beach with palm trees

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