Search Vacation Homes in Annapolis

Where to?

Dates

May 2026

June 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Annapolis vacation homes

Secluded Log Cabin

Annapolis

Glen J.

AED 766 total

includes taxes & fees

12 May - 13 May

The Sutton House 2 blocks from Main Street & Courthouse Square

Ironton

Brandi

AED 759 total

includes taxes & fees

5 May - 6 May

1 bedroom, iron/ironing board, WiFi, bed sheets

AV Bungalows #9B

Arcadia

Theresa R.

AED 613 total

includes taxes & fees

10 May - 11 May

State ParksBungalowCoffeeBarPet Friendly*Porch

Ironton

Derek R.

AED 970 total

includes taxes & fees

19 May - 20 May

Charming 1860s Renovated Home

Ironton

Kevin S.

AED 1,225 total

includes taxes & fees

6 May - 7 May

AV Bungalows #8

Arcadia

AED 704 total

includes taxes & fees

11 May - 12 May

Arcadia Valley Bungalows #5 with seasonal outdoor pool and year-round swim spa

Arcadia

AED 739 total

includes taxes & fees

11 May - 12 May

AV Bungalows #4

Arcadia

REBECCA G.

AED 697 total

includes taxes & fees

5 May - 6 May

Arcadia Valley Bungalows #6 with heated Swim spa and outdoor pool

Arcadia

"June 2024 and (sing it) "I'm hot. You're hot! He's hot! She's hot! WE'RE HOT! They're HOT! HOT HOT HOT!" Temp records are getting busted but we were happy and cool! Arcadia, MO isa less than half tank trip, including going to the Shut Ins during road construction and MAX A/C!!! We found fun people, good food, the bungalow was nice and cool and the ice maker was on! Neat and clean and you can tell these folks have been working hard. It was HOT when we arrived but the pool was cool and clean, even...

Mary Lou S.

AED 739 total

includes taxes & fees

5 May - 6 May

Arcadia Valley Bungalows #3 with Hot Tub/Outdoor Pool

Arcadia

AED 739 total

includes taxes & fees

5 May - 6 May

AV Bungalows #2

Arcadia

AED 879 total

includes taxes & fees

5 May - 6 May

AV Bungalows #9A with Loft

Arcadia

Allen D.

AED 1,301 total

includes taxes & fees

5 May - 6 May

AV Bungalows #1 with Loft

Arcadia

"The host was incredibly responsive and helpful. And for full transparency, we did not ask the host about this while we were there; however, the hot water in the showers was lukewarm at best. The hot water in the rest of the home was very warm. Also, the loft area was such a unique space. The kids loved it! Unfortunately, we were there when temperatures were in the single digits, so we needed to run the heat. ALL of it settled in the loft, leaving it much cooler everywhere else. The layout and...

Tina T.

AED 1,072 total

includes taxes & fees

17 May - 18 May