Search Holiday Rentals in Annapolis County

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Top Holiday Rentals in Annapolis County

Mersey River Chalets a nature retreat
Exterior

Mersey River Chalets a nature retreat

3.5 star property
9.8 out of 10, Exceptional, (38)
"The property is peaceful and well maintained, and the hostess is wonderful."
The price is 2.842.292 ₫
3.337.419 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Mersey River Chalets a nature retreat
Carleton Inn and Cottages
Front of property

Carleton Inn and Cottages

3.5 star property
9.6 out of 10, Exceptional, (39)
"This property was beautiful & room had everything we needed. Even wine glasses. Would definetly recommend staying here."
The price is 3.391.802 ₫
3.866.654 ₫ total
includes taxes & fees
30 Sept - 1 Oct
Carleton Inn and Cottages
Upper Clements Cottages
Property grounds

Upper Clements Cottages

4.0 star property
9.8 out of 10, Exceptional, (12)
"Would be a perfect place for families!"
The price is 3.979.209 ₫
4.672.349 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Upper Clements Cottages
Port Wade Glamping Domes
Front of property

Port Wade Glamping Domes

4.0 star property
9.8 out of 10, Exceptional, (7)
"This property was amazing!! Top notch experience!!"
Port Wade Glamping Domes
Millyard Recreation Riverfront Cottages
Exterior

Millyard Recreation Riverfront Cottages

2.5 star property
7.8 out of 10, Good, (242)
"Very nice place to stay, highly recommend!"
Millyard Recreation Riverfront Cottages
Beautiful Seaside Cottage
Exterior

Beautiful Seaside Cottage

3.0 star property
8.4 out of 10, Very good, (30)
"Great place. Would definitely stay here again!"
The price is 3.259.162 ₫
4.205.835 ₫ total
includes taxes & fees
2 Oct - 3 Oct
Beautiful Seaside Cottage
78 Montague
Family Cottage, 2 Bedrooms | Beach/ocean view

78 Montague

3.0 star property
7.0 out of 10, Good, (8)
"The property was lovely and the host came to meet us when we arrived. The place was clean and the appliances worked fine; it was a very pleasant overnight stay."
The price is 3.372.853 ₫
4.458.229 ₫ total
includes taxes & fees
3 Oct - 4 Oct
78 Montague
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Annapolis County Hotel Reviews

Port Wade Glamping Domes

Port Wade Glamping Domes

10/10 Excellent
"Glamping at it’s best "
Wendy 2-night trip
Posted 1 day ago
Port Wade Glamping Domes