A white house, a horse grazing, and a field of yellow flowers.

Holiday Homes in Centreville

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Centreville holiday homes

A shower with a handheld showerhead and a wall-mounted faucet.

1. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is AU$407
includes taxes & fees
1 Nov - 2 Nov
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

2. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (48 reviews)
"Great stay"
United States
Michael V.
The price is AU$404
includes taxes & fees
26 Oct - 27 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
A building with a gabled roof and a circular vent on the roof.

3. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is AU$440
includes taxes & fees
26 Oct - 27 Oct
BAYSIDE BUNGALOW
A hotel layout with multiple bedrooms, a bathroom, a kitchen, and a living area.

4. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is AU$664
includes taxes & fees
2 Nov - 3 Nov
Wren Retweet- Country Estate in Center of C’Town
A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

5. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is AU$411
includes taxes & fees
26 Oct - 27 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

6. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful home. Plenty of space inside with great outdoor spaces. Very clean and easy to contact host. Family friendly-would highly recommend!"
United States
Jessica H.
The price is AU$880
includes taxes & fees
27 Oct - 28 Oct
Turnbridge Manor
A bedroom with a bed, a desk, a chair, a ceiling fan, a TV, and a window.

7. Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (43 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is AU$471
includes taxes & fees
26 Oct - 27 Oct
Large 2 bedroom house with private parking in a nice neighborhood
Three birds perched on a wooden structure by the water.

8. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is AU$1,846
includes taxes & fees
25 Oct - 26 Oct
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

9. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Cape Saint Claire
9.2 out of 10, Wonderful, (19 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
The price is AU$806
includes taxes & fees
25 Oct - 26 Oct
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A waterfront walkway with a brick path, a lamp post, and a bench.

10. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is AU$678
includes taxes & fees
16 Nov - 17 Nov
Cozy 2br home w/ parking in downtown Annapolis
A hot tub with a white deck and railing, surrounded by trees and a house in the background.

11. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AU$707
includes taxes & fees
3 Nov - 4 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A kitchen with wooden cabinets, a central island with stools, a refrigerator, and a brick accent wall.

12. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive to questions and very easy to communicate with. The house was amazing and so close to downtown. Would definitely stay again!"
United States
Colleen W.
The price is AU$876
includes taxes & fees
26 Oct - 27 Oct
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

13. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is AU$1,708
includes taxes & fees
26 Oct - 27 Oct
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

14. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
9.4 out of 10, Exceptional, (3 reviews)
"Great little house on a perfect location"
United States
Amy T.
The price is AU$792
includes taxes & fees
26 Oct - 27 Oct
Historic Row Home in Downtown Annapolis
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

15. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AU$797
includes taxes & fees
17 Nov - 18 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
A modern kitchen with a central island, built-in oven, and microwave.

16. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (13 reviews)
"Great location, very clean, and the host was very responsive!"
United States
Heather B.
The price is AU$728
includes taxes & fees
27 Oct - 28 Oct
Cute bungalow blocks to Stadium
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

17. Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (7 reviews)
"Great property, great location. Host was super responsive and accommodating! Highly recommended."
United States
Remy S.
The price is AU$1,783
includes taxes & fees
26 Oct - 27 Oct
Luxe Row Home Steps to USNA Gate 3!
A two-story house with a red roof, a brick chimney, and a small porch.

18. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
8.4 out of 10, Very good, (6 reviews)
"The house was clean. It is clear someone lives there full time and vacated the house for our stay. Their food and clothes remained in the property. It did not bother us, but not something we expected. The AC worked well. The owner communicated there were issues before we arrived that they were working to fix and left the number of the contractor in case we experienced issues. We were there the hottest weekend so far this year and did not have any issues. It does look like they are still...
United States
Michele F.
The price is AU$1,472
includes taxes & fees
25 Oct - 26 Oct
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Interior

19. Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
9.0 out of 10, Wonderful, (10 reviews)
"Great property!"
United States
Michael Z.
The price is AU$795
includes taxes & fees
3 Nov - 4 Nov
Historic Row Home | Hot Tub - 1 Block from Gate 1!
A two-story brick building with a balcony, American flags, and a stone wall.

20. Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Historic District
9.4 out of 10, Exceptional, (28 reviews)
"Our group really enjoyed the large outdoor area on the side of the house. We were part of a larger group in town for a wedding and we were able to host a get together for a fairly large group. Over all the house was very comfortable with a great location near heart of Annapolis."
United States
Paul
The price is AU$2,627
includes taxes & fees
4 Nov - 5 Nov
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Staff was very pleasant. Room was clean and a very nice Breakfast included."
Dean 1-night trip
Posted 7 hours ago
St Michaels Inn

Find out more about Centreville

Centreville Holiday Homes information

Number of reviews
550
Accommodation
499 Holiday Homes
Lowest Price
AU$404
Highest Price
AU$2,627