Selby-on-the-Bay Vacation Rentals

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Vacation Rentals in Selby-on-the-Bay

Edgewater/Mayo Gateaway w/ Hot Tub

9.8 out of 10, Exceptional, (22)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
$596 nightly
The price is $643
Oct 28 - Oct 29
Total with taxes and fees
Edgewater/Mayo Gateaway w/ Hot Tub

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (120)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (234)
"This was a wonderful historic home to vacation in"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (36)
"Fabulous place. We’ll be booking again next year. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (40)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

10.0 out of 10, Exceptional, (13)
"The host was amazing. The property was as described and was perfect for our group. "
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
6.8 out of 10, (5)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
Floating 2 bed 2 bath condo stunning views of the bay

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (193)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Waterfront Getaway, Dock Your Boat & Play!

10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
$303 nightly
The price is $324
Oct 21 - Oct 22
Total with taxes and fees
Waterfront Getaway, Dock Your Boat & Play!

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

9.8 out of 10, Exceptional, (47)
"Our large family of adults and two one-year-olds and a dog had a perfect week. The hosts were kind and responsive, and the home was spacious with lots of room for privacy and being all together. Looking forward to going again!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.4 out of 10, Exceptional, (15)
"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"
$1,089 nightly
The price is $1,241
Oct 20 - Oct 21
Total with taxes and fees
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Luxury Waterfront Executive Family Home Annapolis with All Amenities

7.4 out of 10, Good, (3)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Charming townhome with AC and WiFi in delightful Annapolis

4.0 out of 10, (1)
"This is a room, property owner will be there during your stay. Mattress on The floor. Single pillow, comforter, no top sheet. No curtans, and in a mildly questionable part of town. Owner was very "
$88 nightly
The price is $100
Nov 2 - Nov 3
Total with taxes and fees
Charming townhome with AC and WiFi in delightful Annapolis

Walk to Everything House

10.0 out of 10, Exceptional, (83)
"Clean and nice place to stay"
Walk to Everything House

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

9.4 out of 10, Exceptional, (89)
"This property was a great place for a family to all relax together, play games, and enjoy the water!"
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

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

10.0 out of 10, Exceptional, (218)
"We had a wonderful time. Hosts were very kind and responsive! Beautiful property "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Riverfront Retreat 7mil from MD Renaissance Fest!

9.2 out of 10, Wonderful, (17)
"It was a beautiful and private setting for a family reunion."
Riverfront Retreat 7mil from MD Renaissance Fest!

Large 2 bedroom house with private parking in a nice neighborhood

9.4 out of 10, Exceptional, (28)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
$292 nightly
The price is $333
Nov 2 - Nov 3
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (187)
"Excellent accommodations. Comfortable, good location.One way you could improve is to furnish wash cloths and hand towels. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 star property
10.0 out of 10, Exceptional, (28)
"Absolutely the best Vrbo we have ever encountered! Beautiful, charming, accommodating, family friendly and in an excellent location. Our stay was exceptional. "
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
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

Find out more about Selby-on-the-Bay

Everything you need to know about Selby-on-the-Bay 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 Selby-on-the-Bay 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 Selby-on-the-Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Selby-on-the-Bay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Selby-on-the-Bay. 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 Selby-on-the-Bay 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 $100 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 Selby-on-the-Bay rentals

At Expedia, we put the best Selby-on-the-Bay 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 Selby-on-the-Bay 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 Selby-on-the-Bay 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 Selby-on-the-Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Edgewater/Mayo Gateaway w/ Hot Tub: This highly rated vacation home rental in Selby-on-the-Bay offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind.

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 Annapolis Harbour Center 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.