Selby-on-the-Bay Vacation Rentals

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Our top choices for Selby-on-the-Bay vacation rentals

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is CA $108
CA $366 total
includes taxes & fees
Apr 8 - Apr 9
Charming Coastal/Country Home w/3 Acres & Sauna!

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is CA $349
CA $588 total
includes taxes & fees
Apr 7 - Apr 8
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (38 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is CA $188
CA $461 total
includes taxes & fees
Apr 7 - Apr 8
Large 2 bedroom house with private parking in a nice neighborhood

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, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is CA $108
CA $366 total
includes taxes & fees
Apr 12 - Apr 13
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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
The price is CA $240
CA $673 total
includes taxes & fees
Apr 7 - Apr 8
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is CA $345
CA $646 total
includes taxes & fees
Apr 7 - Apr 8
Waterfront Oasis of Annapolis Star

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (19 reviews)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is CA $166
CA $523 total
includes taxes & fees
Apr 12 - Apr 13
Walk to Beach! King Bed & Free Beach Passes

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is CA $271
CA $659 total
includes taxes & fees
Apr 12 - Apr 13
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is CA $276
CA $724 total
includes taxes & fees
Apr 7 - Apr 8
Cute bungalow blocks to Stadium

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, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is CA $220
CA $676 total
includes taxes & fees
Apr 20 - Apr 21
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in
Glen Burnie
8.6 out of 10, Excellent, (10 reviews)
"Jordan was a great host and communicated in a timely and professional manner. Outdoor space and pool were lovely for the hot sunny weekend. "
United States
Ellie F.
The price is CA $153
CA $207 total
includes taxes & fees
Apr 8 - Apr 9
Secluded Tiny Pool House -Private Pool -Self Check in

Lower Level Loft - Adorable Studio Apt. Near BWI

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.4 out of 10, Exceptional, (14 reviews)
"No complaints"
United States
Shelby B.
The price is CA $86
CA $149 total
includes taxes & fees
Apr 9 - Apr 10
Lower Level Loft - Adorable Studio Apt. Near BWI

Waterfront Unit | Dock, Kayaks & SUPs Included

Waterfront Unit | Dock, Kayaks & SUPs Included
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"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.
The price is CA $138
CA $480 total
includes taxes & fees
Apr 7 - Apr 8
Waterfront Unit | Dock, Kayaks & SUPs Included

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
The price is CA $418
CA $602 total
includes taxes & fees
Apr 7 - Apr 8
40' Bristol sailboat with spectacular views

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is CA $174
CA $547 total
includes taxes & fees
Apr 7 - Apr 8
Pool Loft Suite | Bay Access & Beach Passes

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is CA $233
CA $827 total
includes taxes & fees
Apr 13 - Apr 14
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.8 out of 10, Exceptional, (8 reviews)
"Great place!"
United States
Chris A.
The price is CA $230
CA $570 total
includes taxes & fees
Apr 9 - Apr 10
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Cute, Cozy 2-bedroom house in near Annapolis with water access

Cute, Cozy 2-bedroom house in near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (4 reviews)
"Host was wonderful! Enjoyed our weekend in a very clean, comfortable and peaceful place. Look forward to returning in warmer weather."
United States
Katherine P.
The price is CA $107
CA $310 total
includes taxes & fees
Apr 7 - Apr 8
Cute, Cozy 2-bedroom house in near Annapolis with water access

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (13 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is CA $427
CA $870 total
includes taxes & fees
Apr 20 - Apr 21
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Historic Annapolis Home | 2 Blocks to Main St

Historic Annapolis Home | 2 Blocks to Main St
Historic District
10.0 out of 10, Exceptional, (16 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is CA $278
CA $913 total
includes taxes & fees
Apr 7 - Apr 8
Historic Annapolis Home | 2 Blocks to Main St
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 Selby-on-the-Bay Hotel Reviews

Find out more about Selby-on-the-Bay

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 Selby-on-the-Bay. 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

Are there vacation rentals in Selby-on-the-Bay?

Yes, there are vacation rentals near top attractions in Selby-on-the-Bay, or you can go with a more remote option if you're looking for relaxation.

What's the top vacation rental in Selby-on-the-Bay?

Sweet Bamboo Beach Cottage: This vacation home rental near Selby-on-the-Bay is located on the beach and has a patio, a garden, 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.

How many vacation rentals are there in Selby-on-the-Bay?

Expedia has 6 vacation rentals for your stay in Selby-on-the-Bay.

What can I see and do in Selby-on-the-Bay?

Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Maryland Quiet Waters Park. London Town and Triton Beach are a couple of places you'll find in the larger area.

What are vacation rentals like in Selby-on-the-Bay?

Vacation rentals are private accommodations you can stay in for a couple days or more in Selby-on-the-Bay. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.