Search results; Over 1,000 places in Middletown

Prices include all fees

Explore more homes

Guest favorite
Guest suite in Middletown
Charming Private Basement Retreat in Middletown
1 queen bed
Jun 7 – 12
ﺩ.ﺇ2,476 for 5 nights
for 5 nights
4.83 out of 5 average rating, 35 reviews
Guest favorite
Townhouse in Middletown
Luxury Townhome w/free parking
3 beds
Jun 1 – 6
ﺩ.ﺇ3,589 for 5 nights
for 5 nights
5.0 out of 5 average rating, 24 reviews
Guest favorite
Room in Smyrna
Stay with Claudina
Modern King size bedroom Wi-Fi, parking, kitchen
Jun 1 – 6
ﺩ.ﺇ883 for 5 nights
for 5 nights
5.0 out of 5 average rating, 35 reviews
Top guest favorite
Apartment in Chesapeake City
Private entrance King Suite
Free cancellation
Jun 21 – 26
ﺩ.ﺇ3,323 for 5 nights
for 5 nights
5.0 out of 5 average rating, 26 reviews
Top guest favorite
Room in Elkton
Stay with AnnMarieTugboat dispatch,
Country Get Away 1 Room Apartment
Jun 16 – 21
ﺩ.ﺇ1,709 for 5 nights
for 5 nights
4.98 out of 5 average rating, 236 reviews
Guest favorite
Townhouse in Middletown
Spacious 3 bed/1.5 bath townhome with free parking
3 beds
Jul 14 – 19
ﺩ.ﺇ3,917 for 5 nights
for 5 nights
4.93 out of 5 average rating, 44 reviews
Guest favorite
Apartment in Warwick
Cozy peaceful apartment
Jun 1 – 6
ﺩ.ﺇ3,250 for 5 nights
for 5 nights
4.89 out of 5 average rating, 27 reviews
Guest favorite
Room in Chesapeake City
Stay with TammyFood and beverage,
Cafe on the Bay 2- breakfast included!
Jun 1 – 6
ﺩ.ﺇ2,476 for 5 nights
for 5 nights
4.91 out of 5 average rating, 264 reviews
Top guest favorite
Apartment in Chesapeake City
Vista 27 Luxury Ches City Apt on Waterfront Farm
Free cancellation
Jun 1 – 6
ﺩ.ﺇ3,402 for 5 nights
for 5 nights
4.97 out of 5 average rating, 33 reviews
Room in Middletown
Stay with JohnnyHosting for 7 years,
Pie's Place- Queen bedroom
Jun 1 – 6
ﺩ.ﺇ2,583 for 5 nights
for 5 nights
4.77 out of 5 average rating, 31 reviews
Top guest favorite
Home in Millington
Anchors Away
Free cancellation
Jun 1 – 6
ﺩ.ﺇ7,318 for 5 nights
for 5 nights
5.0 out of 5 average rating, 22 reviews
Home in Newark
Cozy 1 Bedroom/1 Bath Near UD
1 queen bed
Jun 1 – 6
ﺩ.ﺇ1,552 for 5 nights
for 5 nights
New place to stay
Top guest favorite
Home in Chesapeake City
McReynolds-Woods House -Private 3 Bedroom Home
Free cancellation
Jun 1 – 6
ﺩ.ﺇ8,373 for 5 nights
for 5 nights
5.0 out of 5 average rating, 34 reviews
Guest favorite
Place to stay in Havre de Grace
Delightful 12x16 Glamping Gazebo/Tent
Free cancellation
Jun 1 – 6
ﺩ.ﺇ1,804 for 5 nights
for 5 nights
4.98 out of 5 average rating, 94 reviews
Superhost
Apartment in Elkton
Cozy & Affordable 2-BR Apartment- Elkton, MD
Free cancellation
Jun 8 – 13
ﺩ.ﺇ3,207 for 5 nights
for 5 nights
New place to stay
Top guest favorite
Home in Chesapeake City
Chesapeake City Charm at the Boho House!
Free cancellation
Jun 16 – 21
ﺩ.ﺇ11,365 for 5 nights
for 5 nights
5.0 out of 5 average rating, 46 reviews
Top guest favorite
Home in Chesapeake City
Charming, updated home in Historic Chesapeake City
5 beds
Jun 1 – 6
ﺩ.ﺇ8,987 for 5 nights
for 5 nights
4.98 out of 5 average rating, 59 reviews
Guest favorite
Cottage in Earleville
Cottage at the bay We are pet friendly
Free cancellation
Jun 1 – 6
ﺩ.ﺇ3,444 for 5 nights
for 5 nights
5.0 out of 5 average rating, 10 reviews