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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Browse Select Centreville Holiday Homes

Our top choices for Centreville holiday homes

HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is £339
includes taxes & fees
25 Aug - 26 Aug
HGTV quality, private guest suite, country getaway with hot tub & fire pit
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Marina

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

9.6 out of 10, Exceptional, (30)
"Nice and peaceful stay for a quick local getaway. "
The price is £220
includes taxes & fees
28 Aug - 29 Aug
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (39)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is £220
includes taxes & fees
27 Aug - 28 Aug
Relax on Kent Island in 3 Bedroom Home w/Waterview
Turnbridge Manor
Property grounds

Turnbridge Manor

9.8 out of 10, Exceptional, (12)
"We rented this wonderful home for Christmas and had the most relaxing time. The house is just as advertised and the owner a delight to work with. We especially loved the proximity to the square and how walkable it was to everything. I can’t wait to rent it again during warm weather to enjoy all the wonderful porches and the outdoor area."
Turnbridge Manor
Charming Pet-Friendly Stay - Near Bay & Beaches.
Interior

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (3)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is £383
includes taxes & fees
25 Aug - 26 Aug
Charming Pet-Friendly Stay - Near Bay & Beaches.
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is £316
includes taxes & fees
25 Aug - 26 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Terrace/patio

Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is £341
includes taxes & fees
25 Aug - 26 Aug
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Historic 3 BR Home - 15 Min Walk to N-MC Stadium
3 bedrooms, iron/ironing board, WiFi, bed sheets

Historic 3 BR Home - 15 Min Walk to N-MC Stadium

The price is £457
includes taxes & fees
3 Sept - 4 Sept
Historic 3 BR Home - 15 Min Walk to N-MC Stadium
Cute bungalow blocks to Stadium
Fridge, microwave, oven, stovetop

Cute bungalow blocks to Stadium

10.0 out of 10, Exceptional, (5)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
The price is £396
includes taxes & fees
25 Aug - 26 Aug
Cute bungalow blocks to Stadium
Neptune by the Water - Pet Friendly Fenced Yard
Fridge, microwave, oven, stovetop

Neptune by the Water - Pet Friendly Fenced Yard

9.6 out of 10, Exceptional, (10)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is £411
includes taxes & fees
26 Aug - 27 Aug
Neptune by the Water - Pet Friendly Fenced Yard
Annapolis Retreat - 7 mins from downtown Annapolis!
Microwave, oven, stovetop, dishwasher

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (2)
"The house was roomy, perfect for a large group and it was very clean and cozy. They also provided everything that was needed to have a comfortable stay."
The price is £433
includes taxes & fees
25 Aug - 26 Aug
Annapolis Retreat - 7 mins from downtown Annapolis!
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, oven, stovetop

Bayside Cottage steps from Rock Hall Harbor

10.0 out of 10, Exceptional, (2)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
The price is £293
includes taxes & fees
22 Sept - 23 Sept
Bayside Cottage steps from Rock Hall Harbor
Historic Row Home 1 Block from Gate 1 at USNA!
Interior

Historic Row Home 1 Block from Gate 1 at USNA!

10.0 out of 10, Exceptional, (1)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
The price is £531
includes taxes & fees
25 Aug - 26 Aug
Historic Row Home 1 Block from Gate 1 at USNA!
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (46)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is £228
includes taxes & fees
25 Aug - 26 Aug
BAYSIDE BUNGALOW
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
On the beach, sun-loungers, beach towels

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is £1,046
includes taxes & fees
25 Aug - 26 Aug
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
New! All Star Annapolis Retreat - Walk to Stadium
Exterior

New! All Star Annapolis Retreat - Walk to Stadium

10.0 out of 10, Exceptional, (5)
"Beautiful and comfortable property! We enjoyed our time here and would book it again. "
New! All Star Annapolis Retreat - Walk to Stadium
Stunning 4 BR Home - Walking Distance to Stadium
Fridge, microwave, oven, stovetop

Stunning 4 BR Home - Walking Distance to Stadium

The price is £517
includes taxes & fees
25 Aug - 26 Aug
Stunning 4 BR Home - Walking Distance to Stadium
Historic Row Home in Downtown Annapolis
Fridge, microwave, oven, stovetop

Historic Row Home in Downtown Annapolis

The price is £507
includes taxes & fees
25 Aug - 26 Aug
Historic Row Home in Downtown Annapolis
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Interior

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

The price is £380
includes taxes & fees
3 Sept - 4 Sept
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Annapolis Baystone House
TV, fireplace, offices

Annapolis Baystone House

10.0 out of 10, Exceptional, (1)
"The Annapolis bayside house is fully equipped with everything you would need while away from your home. Nicely decorated, clean, high tech features , plenty of games nice bedding, convenient location. It’s a townhouse with three floors so not conducive for elderly people . I would Definately rent this house again"
The price is £560
includes taxes & fees
1 Sept - 2 Sept
Annapolis Baystone House
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 Centreville Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Check in/out went smoothly. Room was big and comfortable. Low pressure in shower."
Linda 2-night trip
Posted 20 hours ago
Comfort Inn & Suites Chestertown