Sunderland Holiday Rentals

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Check prices for these dates

Tonight
27 Nov - 28 Nov
Tomorrow
28 Nov - 29 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Holiday Rentals in Sunderland

Marina
Floating 2 bed 2 bath condo stunning views of the bay

Houseboat in Stevensville

2.0 star property
6.4 out of 10, (7)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cottage in Cambridge

10.0 out of 10, Exceptional, (15)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Cottage in North Beach

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great location! Everything was on hand and it was an easy sweet little cottage to be in.It was clean and very functional with the added bonus of being so close to all the activity in North Beach.Heather was responsive and obviously cares about her guests and their stay.Highly recommend! "
United States
Georgina P.
The price is HK$996
HK$2,152 total
includes taxes & fees
30 Nov - 1 Dec
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub

Holiday Home in Edgewater

9.8 out of 10, Exceptional, (24)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
Edgewater/Mayo Gateaway w/ Hot Tub
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!

Mobile Home in Edgewater

10.0 out of 10, Exceptional, (3)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
Waterfront Getaway, Dock Your Boat & Play!
Smart TV, fireplace, books, offices
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Holiday Home in Port Republic

10.0 out of 10, Exceptional, (124)
"Well, what a great time we had at this house the house is exactly as advertised, tidy, clean, comfortable, everything close. The view was beautiful, our vacation was amazing. Alicia was very responsive to any question that we had. We definitely would rent again!"
United States
Misael A A.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Outdoor dining
Discover tranquility near Calvert Cliffs

Holiday Home in Saint Leonard

9.8 out of 10, Exceptional, (18)
"Comfortable beds, large house with awesome views…had a great experience"
United States
Deborah R.
Discover tranquility near Calvert Cliffs
Beach nearby, sun-loungers, beach towels
The Blue Crab Beach House - Free beach passes

Holiday Home in North Beach

10.0 out of 10, Exceptional, (76)
"Excellent communication and place "
United States
Desiree
The Blue Crab Beach House - Free beach passes
3 bedrooms, iron/ironing board, travel cot, free WiFi
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Holiday Home in Prince Frederick

9.6 out of 10, Exceptional, (4)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is HK$1,400
HK$2,836 total
includes taxes & fees
1 Dec - 2 Dec
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Fridge, microwave, oven, stovetop
The Middle Point Cabin in Saint Michaels

Cottage in Neavitt

9.8 out of 10, Exceptional, (56)
"We had a great stay. The cottage is just like the pictures. Nice area…lots of things to do."
United States
Michael
The Middle Point Cabin in Saint Michaels
Outdoor dining
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Holiday Home in Tracys Landing

9.8 out of 10, Exceptional, (50)
"Our week at Jacob's property was excellent. It was the perfect location for a family getaway, and Jacob was helpful and responsive."
United States
Brett F.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Dining
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Cabin in Port Republic

10.0 out of 10, Exceptional, (181)
"Everything about this cabin was just what we were looking for! From the initial booking until we left we were taken care of by Brett. The pictures on-line were spot on but seeing the bay view in person from the windows and deck took my breath. There was a lot to do and we took advantage of close by activities (hiking, paddle-boarding, kayaking, jet skiing) but the cabin is a destination in itself with it's peaceful and calm surroundings. We were blessed with beautiful sunrises, hummingbirds and...
United States
Vicki K.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Terrace/patio
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Holiday Home in Cambridge

9.8 out of 10, Exceptional, (133)
"This was our second time staying here. Love the location and size of the property. Plenty of space for the kids to play catch, ride bikes, and lots of crabbing and fishing. "
United States
Joe B.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Dining
Million Dollar View of the Chesapeake Bay

Holiday Home in Deale

9.8 out of 10, Exceptional, (130)
"Absolutely beautiful and peaceful location. Everything was appreciated- the games for lazy evenings, the crab pots, the comfortable beds and living spaces. Stunning view!"
United States
Michelle D.
Million Dollar View of the Chesapeake Bay
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Holiday Home in Stevensville

9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is HK$613
HK$2,026 total
includes taxes & fees
2 Dec - 3 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Interior
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Cottage in Stevensville

10.0 out of 10, Exceptional, (56)
"It’s a fantastic property!! Perfect for a getaway weekend. Everything was as described. A great place to stay home and enjoy all the amenities."
United States
Kurt H.
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Private beach
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Holiday Home in Sherwood

10.0 out of 10, Exceptional, (20)
"Fantastic property"
United States
Harvey W.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Smart TV, printers
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Holiday Home in Mechanicsville

10.0 out of 10, Exceptional, (7)
"This is a beautiful cottage in a quiet country setting. Our travel had us arriving a little early and Hannah graciously allowed us to check in early. Bathroom doors were attractive and trendy but did not lock or offer complete privacy. "
United States
Cloyd & Bethanne G.
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Fridge, microwave, oven, stovetop
Bay views with kayaks, bikes, fire pit, crabbing and more

Holiday Home in Shady Side

9.6 out of 10, Exceptional, (21)
"Cute cottage in quiet neighborhood for a get away to the Eastern shore. Description is accurate and Mary was easy to communicate with. We enjoyed our stay."
United States
Kristin A.
Bay views with kayaks, bikes, fire pit, crabbing and more
Property grounds
Stunning Water Front Home with Private Dock and Beach and Sunsets

Holiday Home in Lusby

10.0 out of 10, Exceptional, (26)
"Great place. Would definitely stay here again. "
United States
Joshua M.
Stunning Water Front Home with Private Dock and Beach and Sunsets
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 Sunderland Hotel Reviews

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"roomy and spacious"
DENNIS RYAN 1-night trip
Posted 2 days ago
Sonesta ES Suites Annapolis

Find out more about Sunderland

Search for holiday rentals in Sunderland on Expedia! You can easily find your home rentals, villas, holiday apartments in Sunderland using one of the methods below:

  • View our selection of featured holiday rentals in Sunderland
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Look no further and take a look at our great range of rental properties in Sunderland!

Frequently asked questions

Can I find holiday rentals in Sunderland?

Yes, there are holiday rentals close to the most popular sights in Sunderland, 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 Sunderland has to offer?

Edgewater/Mayo Gateaway w/ Hot Tub: This holiday home rental outside of Sunderland offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

What’s there to see and do in Sunderland?

Explore the area and family-friendly sights such as Chesapeake Beach Water Park, or get out into nature at a spot like Breezy Point Beach. Rod n Reel Charter Fishing and Chesapeake Beach Railway Museum are a couple of places you'll find in the wider area.

What’s a holiday rental in Sunderland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sunderland. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for families.