Holiday Homes in Port Deposit

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Port Deposit

Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Property grounds
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
9.6 out of 10, Exceptional, (52)
"Nice. Close to downtown. Great backyatd"
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Sweet Little Home Away From Home, North East, MD
Microwave, oven, stovetop, dishwasher
Sweet Little Home Away From Home, North East, MD
10.0 out of 10, Exceptional, (1)
"Top notch experience. "
Sweet Little Home Away From Home, North East, MD
Waterfront house with amazing views. Top of the Chesapeake
On the beach, sun-loungers, beach towels
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (93)
"From booking to check out Matt was great! Property was clean and felt like home. The water view was beautiful and just sitting out and enjoying the water from the deck, the kids were in the water our entire stay or fishing off the pier. We definitely will be booking again!"
Waterfront house with amazing views. Top of the Chesapeake
Captivating Chesapeake experience
Beach
Captivating Chesapeake experience
10.0 out of 10, Exceptional, (249)
"We had a wonderful stay at this beautiful property. The water views are amazing and it was so relaxing! The house was very clean and well maintained. Everything we expected it to be from the listing, actually more charming and comfortable than the pictures show. Thank you. "
Captivating Chesapeake experience
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun-loungers, beach towels
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.6 out of 10, Exceptional, (34)
"Debbie was a great communicator and very generous with allowing us to check in early - such a treat! The kitchen is well appointed and we were all impressed with the great bath towels and bed linens. The one thing to point out is that while this is a water front property, I didn't realize from the pictures, that its on a cliff, so you couldn't fish from the front of the property like I was imagining prior to arriving; luckily the walk to the beach was a short one so our kiddos fished from...
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Top of the Chesapeake - Minutes from Historic Charlestown
View from property
Top of the Chesapeake - Minutes from Historic Charlestown
9.8 out of 10, Exceptional, (133)
""Oh, down in Chesapeake Catching rock around fishing creek The soft-shell crabs play hide and seek Down in Chesapeake." We LOVE the Chesapeake area and have stayed up and down the bay, mostly midway and lower. This area on the upper bay is so close to Philadelphia and, although there are tourists around like us, it doesn't feel touristy unless you go into North East, downtown (which is still worth eating a meal or getting ice cream in that cute little town)! Our stay felt private, and we had...
The price is AU$905
includes taxes & fees
30 Sept - 1 Oct
Top of the Chesapeake - Minutes from Historic Charlestown
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
A heated pool
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
9.4 out of 10, Exceptional, (32)
"We had a great time in the pool, fishing off dock, paddle boarding, kayaking and swimming. The kids (5 under 8) loved playing in the bAsement."
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Fridge, microwave, oven, stovetop
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, (33)
"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Exterior
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, (95)
"Older home that was very clean. met our needs well. was close to the University of Delaware. "
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Chesapeake City Quiet Overlook
Property grounds
Chesapeake City Quiet Overlook
10.0 out of 10, Exceptional, (11)
"My wife and I booked Jane’s house for our wedding weekend in Chesapeake city. Jane allowed us to use her property for our wedding of 40 ppl. She could not have been nicer or more accommodating for this special occasion. She responded to all of our questions quickly and even made special offers to make our wedding weekend even more special. I cannot say enough nice things about Jane. The house and property were gorgeous in a really great location along the canal in Chesapeake city. The views...
Chesapeake City Quiet Overlook
Amazing Waterfront Home on the Bush River
Terrace/patio
Amazing Waterfront Home on the Bush River
10.0 out of 10, Exceptional, (17)
"We stayed here for our wedding weekend leading up to the big day with our families and this couldn't have asked for a better location and place to relax."
Amazing Waterfront Home on the Bush River
Clean and Cozy 2 BR home blocks away from downtown
Fridge, microwave, oven, stovetop
Clean and Cozy 2 BR home blocks away from downtown
10.0 out of 10, Exceptional, (19)
"We had a wedding to attend and decided to make a long weekend out of it and so glad we did! The home was beautiful, clean and had everything one could need! We thoroughly enjoyed our stay and relaxation at this house. Will definitely be back again! Thanks to Phyllis our host who was amazing and even had flowers with a nice welcome note..perfect touch."
Clean and Cozy 2 BR home blocks away from downtown
Peaceful Pines Hideaway
Exterior
Peaceful Pines Hideaway
2.5 star property
10.0 out of 10, Exceptional, (2)
"This beautiful home is very clean, very comfortable and large with a beautiful backyard to enjoy. "
Peaceful Pines Hideaway
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Exterior
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
10.0 out of 10, Exceptional, (51)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Lancaster co. farmhouse in the heart of amish country
Terrace/patio
Lancaster co. farmhouse in the heart of amish country
10.0 out of 10, Exceptional, (128)
"This was one of our most favorite family vacations to date. My son actually said “this house is better than Disney World!”. The pictures don’t do it justice. The detail of this house is incredible and it’s immaculately clean. It was the best stocked rental that we have ever stayed in. Mim was super sweet, and greeted us the day after our arrival. She gave us local suggestions for ice cream and Amish run stores which we went to and loved! This place was like a Magnolia Homes magazine, and we...
Lancaster co. farmhouse in the heart of amish country
Historic home in the heart of Main Street- walkable to shops and restaurants
Interior
Historic home in the heart of Main Street- walkable to shops and restaurants
10.0 out of 10, Exceptional, (9)
"We really enjoyed the property. The location was within walking distance to the downtown area providing many food and shopping options. We were in MD for a lacrosse tournament which was minutes away from the house. The house was recently renovated, clean and bright. We had more than enough space for our group of 8."
Historic home in the heart of Main Street- walkable to shops and restaurants
Sunset River Cottage encapsulates nautical romance.
Outdoor spa tub
Sunset River Cottage encapsulates nautical romance.
8.8 out of 10, Excellent, (10)
"Great view and cute cottage"
Sunset River Cottage encapsulates nautical romance.
Upper Chesapeake Getaway - Newly Renovated
Property grounds
Upper Chesapeake Getaway - Newly Renovated
9.8 out of 10, Exceptional, (12)
"We had a fabulous time and want you to come and decorate all of our homes! Just beautiful! The only suggestion is maybe swap out that thermostat for a simpler one. We spent way too much time fussing with that. Thank-you for everything!!! We’ll be back!! "
Upper Chesapeake Getaway - Newly Renovated
Place to Stay In Airville
Exterior
Place to Stay In Airville
8.0 out of 10, Very good, (1)
"The property itself was great. Was very clean, the front and backyards were very well done. The only challenges we had were lack of towels and the check-in process. We had a group of seven stay, there were only four towels, and we were not informed to bring additional. The only other challenge was accessing the property - we did not have the access code upon arrival and had to wait longer than anticipated for the owner to respond. These challenges were minor in nature, and our group...
Place to Stay In Airville
Spacious North East Home w/ Fenced Yard & Fire Pit
Property grounds
Spacious North East Home w/ Fenced Yard & Fire Pit
10.0 out of 10, Exceptional, (3)
"We came to town for a lacrosse tournament. Easy to get to the fields from this location. Our two families were so happy with the wonderful home and the spaces were fantastic! The towels are so soft. The photos do not do justice to the space and welcoming feeling you get. We were pleasantly pleased with our stay! Walking distance to fun restaurant and not too far from town. We would love to come back some time. Thanks for sharing your home."
Spacious North East Home w/ Fenced Yard & Fire Pit
Don't see what you're looking for?
See all available properties in Port Deposit
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
Sign in
Sign up, it's free

Other property types in Port Deposit

Quarry Landing - Center of Town & River View - 3 Bedroom
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom
9.8 out of 10, Exceptional, (7)
"On a small hillside. Very quaint accommodation. Close to restaurants and river. Parking a little difficult to figure out, train is a bit loud and frequent but everything else was as advertised and nice. "
The price is AU$339
includes taxes & fees
29 Sept - 30 Sept
Quarry Landing - Center of Town & River View - 3 Bedroom
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (27)
"The accomodations were VERY nice. The wifi was not sufficient for me to work in the room, but they allowed us to sit on the deck and work instead."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Property grounds
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
9.6 out of 10, Exceptional, (52)
"Nice. Close to downtown. Great backyatd"
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
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.