Holiday Rentals in Sunderland

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Holiday Rentals in Sunderland

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (209)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (44)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (57)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (247)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier

Private Cottage on gated estate

10.0 out of 10, Exceptional, (23)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (36)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is €224
includes taxes & fees
17 Jun - 18 Jun
Relax on Kent Island in 3 Bedroom Home w/Waterview

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The Cottage

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (4)
"A few local spots to eat were great in the morning especially the Tighlman Market! Market has all you need to stock up with groceries and is just 2 minutes from the house."
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

10.0 out of 10, Exceptional, (102)
"Had a wonderful, peaceful stay."
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (40)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (175)
"Great time!! Floridians playing in the snow!! Cozy fire afterwards in the fireplace. Picturesque drive up to the Navy Cabin, deer playing in the snow too."
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Wright's Cottage- Pet's Welcome & EV Charging

9.8 out of 10, Exceptional, (11)
"Property was in new condition, very well decorated and comfortable. A bit larger than what we needed; but, comfy."
The price is €356
includes taxes & fees
24 Jun - 25 Jun
Wright's Cottage- Pet's Welcome & EV Charging

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (28)
"Great location, close to the beach and restaurant. Cozy and comfortable, with a beautiful view of sunset. "
Chesapeake Houseboat Getaway on Kent Island, Maryland

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

10.0 out of 10, Exceptional, (44)
"We had a great stay! Thanks."
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Waterfront Escape Near Annapolis

10.0 out of 10, Exceptional, (13)
"Good stay. Excellent location and facility es"
Waterfront Escape Near Annapolis

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (26)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

10.0 out of 10, Exceptional, (1)
"We stayed here for 2 nights with 3 other couples. Bedrooms are very spacious. There are 2 rollaway beds and it looks like a pack n play as well for families with kids. Both couches pull out into beds. Everything was perfect for our needs. You can fit 3 cars in the front driveway but there’s also 2 spots available behind the house. You can also see the Bay from the front windows. Close to stores and gas as well. Would definitely recommend! "
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (36)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is €442
includes taxes & fees
22 Jun - 23 Jun
Beautiful Waterfront Retreat in Cambridge!

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (115)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Grandma's Summer House @ Beverly Beach

9.8 out of 10, Exceptional, (6)
" Retreating from a construction project in our home, we landed in Grandma's Cottage. What a delightful semi-vactation. Lovely cottage, kind and friendly commuity srrouned by water and nature parks."
Grandma's Summer House @ Beverly Beach
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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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?

Relax on Kent Island in 3 Bedroom Home w/Waterview: This holiday home rental outside of Sunderland offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Upper Yough River. 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.