Holiday Rentals in Perry Point

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Our top choices for Perry Point holiday rentals

10.0 out of 10, Exceptional, (31)
"Wow such a wonderful place, clean, warm, and full of everything you need."
United States
Oswaldo S.
The price is €184
includes taxes & fees
15 Dec - 16 Dec
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
10.0 out of 10, Exceptional, (20)
"Great waterfront home with sunset views! Plenty of space for our group, very clean, and the hot tub was a perfect bonus. Peaceful, relaxing, and just as described. We’d definitely come back!"
United States
Kaylyn G.
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront
8.6 out of 10, Excellent, (7)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
United States
Benjamin J.
The price is €732
includes taxes & fees
11 Dec - 12 Dec
Luxury Waterfront Home Built for Entertaining!
9.8 out of 10, Exceptional, (59)
"We had an amazing weekend at the cottage. It’s very clean and beautiful! The close walk to the beach is perfect and we had great weather. Would love to stay here again! "
United States
Angela F.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (14)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
United States
Deborah M.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
9.8 out of 10, Exceptional, (44)
"This was our second time staying here and we really love it! It has everything needed and is very close &convenient to any outing we did, The house layout works great for our group of six. Already planning our next trip!! "
United States
Susan G.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.6 out of 10, Exceptional, (14)
"Excellent stay! "
United States
Edward S.
Charming 2-bedroom cabin close to Fair Hill on horse farm
9.8 out of 10, Exceptional, (20)
"Had a good time, grandkids never came out of the pool"
United States
Michael D.
Stunning waterfront villa with indoor pool and kids swing set and play area.
9.8 out of 10, Exceptional, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
The price is €530
includes taxes & fees
11 Dec - 12 Dec
5-bedroom vacation home 5 minutes from historic Charlestown
10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is €313
includes taxes & fees
10 Jan - 11 Jan 2026
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
10.0 out of 10, Exceptional, (179)
"We loved this house and had the best time!!"
United States
Laura C.
Chesapeake Bay House with Dock & Private Beach
10.0 out of 10, Exceptional, (5)
"I appreciated how clean and pleasant it smelled! Then it was a beautiful location with lots of places to eat nearby. My only improvement would have been window curtains, especially in the master bath. "
United States
Leah M.
The price is €243
includes taxes & fees
5 Jan - 6 Jan 2026
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Cabin in Chesapeake City

Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (19)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is €245
includes taxes & fees
11 Dec - 12 Dec
Historic Chesapeake City Stay
9.6 out of 10, Exceptional, (5)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
United States
Rees L.
The price is €161
includes taxes & fees
24 Dec - 25 Dec
Summer Rustic Camping with AC and King Bed
10.0 out of 10, Exceptional, (72)
"Great house close to canal and downtown Chesapeake City!"
United States
Michael M.
Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal
9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is €100
includes taxes & fees
16 Dec - 17 Dec
Country Get Away 1 Bedroom Apartment
10.0 out of 10, Exceptional, (11)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is €201
includes taxes & fees
5 Jan - 6 Jan 2026
Quarry Landing - Center of Town & River View - 3 Bedroom
2.0 star property
5.0 out of 10, (2)
"For our first time trying shared spaces. Over all, the pros; The room was in a nice home in a very quiet and decent housing development. The home was neat decorated in a minimalist style. The bed was very comfortable, pillows and bedding, and hot shower and bath water with soap provided. The kitchen/dining area was just right for cooking and dining and cleaning up had the minimal supplies needed. The sitting areas were very relaxing to watch T.V. and or just lounge. Common bathroom off living...
United States
Nicomedes M R.
The price is €110
includes taxes & fees
18 Dec - 19 Dec
Room #3 in Elkton, MD – Easy Access to I-95

Cabin in Delta

Nature's Grove Cabin
10.0 out of 10, Exceptional, (5)
"Stayed over a few days while in the area for sons wedding. Was a cute and quite area to decompress from the hectic days of getting the wedding day ready!"
United States
Casey K.
Nature's Grove Cabin
9.8 out of 10, Exceptional, (6)
"Beautiful home and property. The house was clean and welcoming and the pool was an absolute delight. Would definitely stay again! "
United States
Julia B.
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.
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.
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Top Perry Point Hotel Reviews

Find out more about Perry Point

Everything you need to know about Perry Point holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Perry Point holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Perry Point holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Perry Point holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Perry Point. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Perry Point holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Perry Point holiday rentals we have selected for you start as low as €100 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Perry Point rentals

At Expedia, we put the best Perry Point holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Perry Point rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Perry Point holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Perry Point. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Perry Point?

Yes, there are holiday rentals close to the most popular sights in Perry Point, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Perry Point has to offer?

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This holiday home rental outside of Perry Point is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

What can I see and do in Perry Point?

While exploring the area, visit family-friendly sights like Plumpton Park Zoo, or get outside and enjoy nature at Garrett Island Beach. Concord Point Lighthouse and Havre de Grace Decoy Museum are a couple of places you'll find in the wider area.

What are holiday rentals like in Perry Point?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Perry Point. Holiday rentals feature extras such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family trips or small group gatherings.