Sunderland Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Sunderland

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

9.4 out of 10, Exceptional, (23)
"A nice, quiet location on the water. Exactly as advertised. We would definitely stay again if we were in the area."
The price is CA $733
CA $1,220 total
includes taxes & fees
Jul 21 - Jul 22
Spacious waterfront home with amazing views, private pier, fishing and crabbing.

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (39)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is CA $338
CA $658 total
includes taxes & fees
Jul 15 - Jul 16
Beautiful Waterfront Retreat in Cambridge!

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

10.0 out of 10, Exceptional, (12)
"very serene, peaceful home on the bay! Amazing getaway! "
The price is CA $478
CA $877 total
includes taxes & fees
Jul 22 - Jul 23
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

#2 Egret Cottage Harris Cove

The price is CA $356
CA $522 total
includes taxes & fees
Jul 24 - Jul 25
#2 Egret Cottage Harris Cove

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (37)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is CA $185
CA $464 total
includes taxes & fees
Jul 23 - Jul 24
Relax on Kent Island in 3 Bedroom Home w/Waterview

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is CA $1,164
CA $1,907 total
includes taxes & fees
Jul 14 - Jul 15
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is CA $1,082
CA $1,795 total
includes taxes & fees
Jul 14 - Jul 15
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Family Luxury: 5BR, GameRm, MovieRm, Kayaks, PingPong, Fire Pit, Beach

8.8 out of 10, Excellent, (3)
"Tommy and Julya were amazing cleanliness, a great location, the host's hospitality, beautiful decor and amenities, and family-friendly aspects. They emphasize the comfort of the space, the convenience of the location, the attentiveness of the host, amazing experience, I would definitely go back. , beachoverall positive experience. "
The price is CA $1,392
CA $2,208 total
includes taxes & fees
Jul 23 - Jul 24
Family Luxury: 5BR, GameRm, MovieRm, Kayaks, PingPong, Fire Pit, Beach

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

9.4 out of 10, Exceptional, (3)
"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. "
The price is CA $437
CA $723 total
includes taxes & fees
Jul 24 - Jul 25
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

Family Beach House: Spacious Deck, Grill & Views

9.2 out of 10, Wonderful, (5)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is CA $233
CA $598 total
includes taxes & fees
Jul 22 - Jul 23
Family Beach House: Spacious Deck, Grill & Views

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (51)
"This home is a wonderful place to stay. We enjoyed so much about it: the fully-equipped kitchen with spices and every appliance you might need, bathrooms with rain showers/good water pressure, decks for outdoor lounging, plenty of space and nice furnishings in the living room, and a quiet neighborhood that isn't too far away from the downtown area. We would love to come back again!"
The price is CA $615
CA $1,138 total
includes taxes & fees
Jul 22 - Jul 23
Charming Annapolis WaterVIEW Home

Charming Cottage with Hot Tub 1 Block from the Bay

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is CA $623
CA $1,124 total
includes taxes & fees
Jul 14 - Jul 15
Charming Cottage with Hot Tub 1 Block from the Bay

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (2)
"The house was roomy, perfect for a large group and it was very clean and cozy. They also provided everything that was needed to have a comfortable stay."
The price is CA $329
CA $854 total
includes taxes & fees
Jul 15 - Jul 16
Annapolis Retreat - 7 mins from downtown 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!!"
The price is CA $417
CA $908 total
includes taxes & fees
Aug 5 - Aug 6
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (1)
"Stay there while my new home was getting work done, house was clean, perfect size for my family. It’s 50 ft to an ice cream shop and laundry mat. Our hoist even included a gift card to the ice cream shop. Great communication and perfect stay for us, felt like home "
The price is CA $246
CA $651 total
includes taxes & fees
Jul 14 - Jul 15
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Beach Home with King Bed and Beach Passes in a Cute Town

10.0 out of 10, Exceptional, (15)
"We had everything we needed in this townhome in North Beach. Nicely decorated, clean and the beds were comfortable! Perfect spot for our girl's weekend."
The price is CA $130
CA $471 total
includes taxes & fees
Jul 17 - Jul 18
Beach Home with King Bed and Beach Passes in a Cute Town

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is CA $301
CA $656 total
includes taxes & fees
Jul 28 - Jul 29
The Cottage

3 BR Pet Friendly Beverly Beach Cottage

9.8 out of 10, Exceptional, (7)
" 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."
The price is CA $205
CA $615 total
includes taxes & fees
Jul 14 - Jul 15
3 BR Pet Friendly Beverly Beach Cottage

Cozy Cottage By The Beach-Pet Friendly

10.0 out of 10, Exceptional, (1)
"Had a great stay. Very clean. As advertised. "
The price is CA $342
CA $700 total
includes taxes & fees
Jul 21 - Jul 22
Cozy Cottage By The Beach-Pet Friendly

Annapolis Gem: Stylish and Cozy

The price is CA $246
CA $651 total
includes taxes & fees
Aug 3 - Aug 4
Annapolis Gem: Stylish and Cozy
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

The Cozy Crab- Your Charming Haven in Lovely North Beach!: This vacation home near Sunderland offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of books.

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.