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Sunderland Vacation Rentals

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Our top choices for Sunderland vacation rentals

1. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is CA $168
CA $420 total
includes taxes & fees
Oct 19 - Oct 20
The Cozy Crab- Your Charming Haven in Lovely North Beach!

2. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $136
CA $476 total
includes taxes & fees
Oct 28 - Oct 29
Beachside Oasis with Beach Passes & King Suite by A Haven Away

3. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (40 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
The price is CA $199
CA $642 total
includes taxes & fees
Nov 9 - Nov 10
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

4. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is CA $204
CA $648 total
includes taxes & fees
Oct 27 - Oct 28
Family Beach House: Spacious Deck, Grill & Views

5. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (3 reviews)
"Warm and cozy- amazing home, beautiful area"
United States
Sodbileg
The price is CA $318
CA $616 total
includes taxes & fees
Oct 19 - Oct 20
Rose Haven Coastal Cottage

6. Plum Point Cottage #1

Plum Point Cottage #1
Calvert County
The price is CA $385
CA $722 total
includes taxes & fees
Oct 24 - Oct 25
Plum Point Cottage #1

7. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is CA $216
CA $381 total
includes taxes & fees
Oct 19 - Oct 20
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

8. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is CA $255
CA $617 total
includes taxes & fees
Oct 19 - Oct 20
3-bedroom house in Deale located on Bay many amenities and great views

9. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is CA $243
CA $535 total
includes taxes & fees
Oct 26 - Oct 27
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

10. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $385
CA $656 total
includes taxes & fees
Oct 19 - Oct 20
Plum Point Cottage #17

11. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is CA $461
CA $818 total
includes taxes & fees
Oct 19 - Oct 20
Plum Point Cottage #15

12. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is CA $183
CA $382 total
includes taxes & fees
Oct 26 - Oct 27
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

13. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (9 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is CA $462
CA $774 total
includes taxes & fees
Oct 19 - Oct 20
Plum Point Cottage #14

14. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is CA $346
CA $715 total
includes taxes & fees
Nov 10 - Nov 11
Sunset Cottage - West River Access and Views!

15. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (56 reviews)
"Our host Adam was wonderful and very communicative. We love the house and the location was just great. It was close to everything and had water views. We will certainly come back again."
United States
Rebecca B.
The price is CA $107
CA $387 total
includes taxes & fees
Oct 19 - Oct 20
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

16. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is CA $293
CA $502 total
includes taxes & fees
Oct 19 - Oct 20
Bright and airy waterfront getaway

17. Just a getaway piece of property

Just a getaway piece of property
Mechanicsville
10.0 out of 10, Exceptional, (1 review)
"Perfect place. Just what i was looking. Definitely recommend to anyone looking to stay close to the MIR track for any event"
United States
David L.
The price is CA $223
CA $321 total
includes taxes & fees
Oct 22 - Oct 23
Just a getaway piece of property

18. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is CA $373
CA $1,041 total
includes taxes & fees
Oct 21 - Oct 22
Family Home on Mayo Peninsula | Deck | Sleeps 10

19. Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (10 reviews)
"Overall I had a wonderful stay... however I wish it was booked for a summertime day... the brand new pool looked very appealing & I wish I couldve enjoyed using it. Will have to try & stay again during the summer for a nice pool day!"
United States
Jay W.
The price is CA $596
CA $1,108 total
includes taxes & fees
Oct 19 - Oct 20
Tranquil Modern Farmhouse

20. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is CA $272
CA $796 total
includes taxes & fees
Oct 19 - Oct 20
Renovated Bungalow | Walk to Beach | Dog-Friendly
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

Find out more about Sunderland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Sunderland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Sunderland?

Yes, we offer vacation rentals near the most popular local attractions in Sunderland, or you can choose a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Sunderland?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This vacation home rental near Sunderland is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 larger area.

What’s a vacation rental in Sunderland like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Sunderland. Vacation rentals feature extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a family trip.