Search Vacation Homes in Annapolis

    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Annapolis

The Sutton House 2 blocks from Main Street & Courthouse Square

10.0 out of 10, Exceptional, (30)
"Great property, well stocked, very informative about the surrounding area. We enjoyed our stay! "
The price is AED 668
AED 850 total
includes taxes & fees
16 Aug - 17 Aug
The Sutton House 2 blocks from Main Street & Courthouse Square

Charming 1860s Renovated Home

8.0 out of 10, Very Good, (16)
"Had a great stay"
The price is AED 694
AED 1,216 total
includes taxes & fees
20 Jul - 21 Jul
Charming 1860s Renovated Home

Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE

10.0 out of 10, Exceptional, (61)
"A very nicely accommodated property set in a peaceful area. Pool was a life saver for us with the weather temps. Very much enjoyed the stay."
Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE

Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.

9.2 out of 10, Wonderful, (12)
"The house was perfect for what we needed. Close to the river yet also gave us our privacy. Great patio and fire pit area. I would definitely stay there again."
The price is AED 1,102
AED 1,848 total
includes taxes & fees
25 Jul - 26 Jul
Gorgeous large rental home in Lesterville MO just minutes from Blackwater River.

Secluded Gate House

10.0 out of 10, Exceptional, (23)
"The gatehouse was amazing. We loved the hiking trails, the grounds, and the location. Campfires were super easy by the lounge. We loved being super close to so much great hiking! We would stay here again in a heartbeat."
Secluded Gate House

Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge

10.0 out of 10, Exceptional, (13)
"Always live to stay here when we head down that way for a sxs trip. "
Black River Retreat 5 Minutes from Jeff’s Canoe Rental /K Bridge

Sunshine Shack at Clearwater Lake (sleeps 6)

8.8 out of 10, Excellent, (10)
"Loved staying a week at Sunshine Shack. The screened in deck is perfect to watch the deer at dusk."
Sunshine Shack at Clearwater Lake (sleeps 6)

Spacious & Secluded Shook Home w/ Private Hot Tub!

9.4 out of 10, Exceptional, (3)
"Very comfortable beds and pillows and the cookies the host left were delicious "
Spacious & Secluded Shook Home w/ Private Hot Tub!

Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins

10.0 out of 10, Exceptional, (30)
"Very friendly, helpful host, clean and cute house. Love the area for shops, and hiking we had a wonderful stay!"
The price is AED 533
AED 926 total
includes taxes & fees
11 Aug - 12 Aug
Pet-Friendly Downtown Ironton minutes away Elephant Rocks, Johnson Shut-ins

Just Minutes from Black River – With WIFI

6.8 out of 10, (5)
"I was pretty disappointed with my experience. We booked and paid for this stay up front. The Tuesday before our stay the host told us the unit was being repaired and that it might not be done for our Friday night stay. We were not contacted prior to this. Turns out the property would be completed and we could still come for our stay. I appreciated the communication up until that point. When we arrived the unit seemed ready. However, there was no central air. There was a window unit in the...
The price is AED 436
AED 796 total
includes taxes & fees
20 Jul - 21 Jul
Just Minutes from Black River – With WIFI

Charming Country Bungalow - perfect for families

10.0 out of 10, Exceptional, (16)
"We enjoyed our stay at this comfortable property. It was nicely decorated and had everything we needed. The host was very responsive. We would stay there again. "
Charming Country Bungalow - perfect for families

Secluded Log Cabin

9.8 out of 10, Exceptional, (22)
"Beds were comfortable, outdoor area was wonderful, not far from town. Enjoyed our stay very much."
Secluded Log Cabin

Rustic Cabin in Hunters' Paradise!

9.8 out of 10, Exceptional, (29)
"We enjoyed our stay and will be back!"
Rustic Cabin in Hunters' Paradise!

Clearwater Lake and Black River Vacation Home

9.6 out of 10, Exceptional, (18)
"Nice clean property! Comfortable beds plenty of seating. "
Clearwater Lake and Black River Vacation Home

Serene Belgrade Hideaway with Fire Pit & Grill!

9.8 out of 10, Exceptional, (6)
"Quiet and peaceful, excellent host, and we would stay again."
Serene Belgrade Hideaway with Fire Pit & Grill!

Newly remodeled offers many amenities with perfect location!

10.0 out of 10, Exceptional, (29)
"We enjoyed the property very much. It was nice and cozy and conveniently located close to Elephant Rocks and Johnson Shut Ins. If we come back to the area, we would definitely stay at this property again. We were in town for a family girls trip and it suited us well."
Newly remodeled offers many amenities with perfect location!

Walk to Dtwn: Ironton Home in Historic District

10.0 out of 10, Exceptional, (1)
"Great location. Place has pretty much everything you would expect if you were staying over at a friends house. Everything worked. Place was really quiet and comfortable. There are two bedrooms, but there is also another private area to sleep. So three couples can fit in here comfortably. Central location, so you are not too far from anything. There are a few restaurants that are less than 10 minutes away. Place was easy to find. The host Lynn, texted us a few days ahead of time letting...
Walk to Dtwn: Ironton Home in Historic District

Cabin near Clearwater Lake

Cabin near Clearwater Lake

Park Model TinyHome with spacious front porch table outdoor furniture and spa.

Park Model TinyHome with spacious front porch table outdoor furniture and spa.
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.
Save an average of 15% on thousands of hotels when you're signed in