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Sunderland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Sunderland vacation rentals

Outdoor dining

1. 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, (37 reviews)
"Such a great house! "
United States
Stephanie V.
$373 nightly
The price is $412
Sep 2 - Sep 3
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach nearby

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, (22 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
$326 nightly
The price is $360
Sep 8 - Sep 9
Total with taxes and fees
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Pool

3. 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.
$439 nightly
The price is $458
Sep 2 - Sep 3
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
Exterior

4. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
$421 nightly
The price is $464
Sep 2 - Sep 3
Total with taxes and fees
Plum Point Cottage #17
Exterior detail

5. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very Good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
$293 nightly
The price is $333
Sep 2 - Sep 3
Total with taxes and fees
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Property grounds

6. 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)
"The owner was very nice "
United States
karen
$237 nightly
The price is $262
Sep 12 - Sep 13
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Terrace/patio

7. 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
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
United States
Joshua T.
$220 nightly
The price is $251
Sep 3 - Sep 4
Total with taxes and fees
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Property grounds

8. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (22 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
$353 nightly
The price is $374
Sep 15 - Sep 16
Total with taxes and fees
Bright and airy waterfront getaway
Interior

9. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place and neighborhood! "
United States
Marci M.
$529 nightly
The price is $538
Sep 8 - Sep 9
Total with taxes and fees
Sunset Cottage - West River Access and Views!
Exterior

10. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
$255 nightly
The price is $275
Sep 2 - Sep 3
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Smart TV

11. 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
$447 nightly
The price is $510
Sep 29 - Sep 30
Total with taxes and fees
3-bedroom house in Deale located on Bay many amenities and great views
TV, fireplace

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, (6 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
$244 nightly
The price is $259
Sep 2 - Sep 3
Total with taxes and fees
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Coffee/tea maker, fridge, microwave, oven

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (12 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.
$494 nightly
The price is $563
Sep 2 - Sep 3
Total with taxes and fees
Renovated Bungalow | Walk to Beach | Dog-Friendly
TV, offices

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
$620 nightly
The price is $707
Sep 2 - Sep 3
Total with taxes and fees
Family Home on Mayo Peninsula | Deck | Sleeps 10
Marina

15. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
$446 nightly
The price is $509
Sep 2 - Sep 3
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Beach

16. Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
9.4 out of 10, Exceptional, (3 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
$653 nightly
The price is $745
Sep 2 - Sep 3
Total with taxes and fees
Londontowne Home | Beach | 3BR
TV

17. Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME

Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME
Waldorf
$582 nightly
The price is $617
Sep 2 - Sep 3
Total with taxes and fees
Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME
Interior

18. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
$566 nightly
The price is $645
Sep 13 - Sep 14
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
Outdoor dining

19. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (76 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
$642 nightly
The price is $732
Sep 2 - Sep 3
Total with taxes and fees
Charming Annapolis WaterVIEW Home
Smart TV

20. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
$552 nightly
The price is $585
Sep 3 - Sep 4
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"Very, very clean! Love the separate toilet/shower and sink. Bed comfy and pillows too! We were extremely satisfied and will be returning!"
Malinda 1-night trip
Posted 18 hours ago
SpringHill Suites by Marriott Annapolis

Find out more about Sunderland

Everything you need to know about Sunderland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sunderland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Sunderland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sunderland vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $259 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sunderland rentals

At Expedia, we put the best Sunderland vacation 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 Sunderland 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 Sunderland vacation.

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

Explore a world of travel with Expedia

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?

Relax on Kent Island in a 4 Bedroom Home w/Waterview!: This vacation home near 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 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 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.