Selby-on-the-Bay Holiday Rentals

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Holiday 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."
The price is AU$808
includes taxes & fees
29 Sept - 30 Sept
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)
"We once again enjoyed our stay here. Perfect location to every where you’d want to go in St. Michael’s! Loved sitting out front looking at the water and park and enjoying music from our front yard. Highly recommend this cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

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

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

10.0 out of 10, Exceptional, (233)
"This was a wonderful historic home to vacation in"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (38)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat

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

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. "
The price is AU$488
includes taxes & fees
29 Sept - 30 Sept
Waterfront Getaway, Dock Your Boat & Play!

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

9.4 out of 10, Exceptional, (14)
"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"
The price is AU$1,918
includes taxes & fees
13 Oct - 14 Oct
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

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

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 ! ! !

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."
The price is AU$508
includes taxes & fees
28 Sept - 29 Sept
Large 2 bedroom house with private parking in a nice neighborhood

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

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.

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!

Walk to Everything House

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

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

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

2.5 star property
10.0 out of 10, Exceptional, (28)
"Wonderful location with walkable restaurant options. Property was cozy and very well appointed. Definitely a re visit."
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

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 "
The price is AU$178
includes taxes & fees
2 Oct - 3 Oct
Charming townhome with AC and WiFi in delightful Annapolis

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
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Selby-on-the-Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Selby-on-the-Bay holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Selby-on-the-Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Selby-on-the-Bay holiday rentals we have selected for you start as low as AU$178 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Selby-on-the-Bay rentals

At Expedia, we put the best Selby-on-the-Bay holiday 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 holiday.

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 holiday rentals in Selby-on-the-Bay?

Yes, there are holiday rentals close to the most popular sights in Selby-on-the-Bay, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Selby-on-the-Bay has to offer?

Edgewater/Mayo Gateaway w/ Hot Tub: This highly rated holiday home rental in Selby-on-the-Bay offers a balcony, a garden and a BBQ 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 that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

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

Expedia has 6 holiday 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 wider area.

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

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Selby-on-the-Bay. Holiday rentals feature amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.