Selby-on-the-Bay Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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

A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is CA $370
CA $981 total
includes taxes & fees
Nov 15 - Nov 16
Family Home on Mayo Peninsula | Deck | Sleeps 10
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (14 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.
The price is CA $272
CA $721 total
includes taxes & fees
Nov 8 - Nov 9
Renovated Bungalow | Walk to Beach | Dog-Friendly
A wooden deck with a white railing, a grill, and a covered table.

3. 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.
The price is CA $297
CA $784 total
includes taxes & fees
Nov 17 - Nov 18
Annapolis Retreat - 7 mins from downtown Annapolis!
A calm lake with a sandy shore, surrounded by trees and houses.

4. 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.
The price is CA $342
CA $955 total
includes taxes & fees
Nov 8 - Nov 9
Londontowne Home | Beach | 3BR
A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

5. Upscale Condo in Annapolis w/Private Parking

Upscale Condo in Annapolis w/Private Parking
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
The price is CA $250
CA $675 total
includes taxes & fees
Nov 17 - Nov 18
Upscale Condo in Annapolis w/Private Parking
A deck with outdoor furniture, a red door, and a house with windows.

6. 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
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is CA $242
CA $507 total
includes taxes & fees
Nov 9 - Nov 10
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (31 reviews)
"Great stay"
United States
Guillaume P.
The price is CA $93
CA $281 total
includes taxes & fees
Nov 15 - Nov 16
Cute, Cozy 2-bedroom house near Annapolis with water access
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

8. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is CA $295
CA $586 total
includes taxes & fees
Dec 1 - Dec 2
Sunset Cottage - West River Access and Views!
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

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

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
9.0 out of 10, Wonderful, (4 reviews)
"A nice, clean, roomy place at a good price--gotta love that. The walk-out basement apartment was located in a compound of units on a quiet dead-end street. This unit is actually toward the back and I spent a little time searching for it. Once there, access to the key and apartment was no problem.The home was well-stocked with kitchen and bathroom supplies, and bedding. Would definitely stay there again."
United States
Rob L.
The price is CA $315
CA $738 total
includes taxes & fees
Nov 16 - Nov 17
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A spacious living room with a large sofa, a coffee table, and a chandelier. There is a kitchen in the background with a dining area.

10. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (10 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
The price is CA $311
CA $776 total
includes taxes & fees
Nov 11 - Nov 12
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
A beach with chairs and a pier in the background.

11. 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, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is CA $278
CA $646 total
includes taxes & fees
Nov 9 - Nov 10
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

12. Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.8 out of 10, Excellent, (16 reviews)
"Very nice home. Definitely recommend!"
United States
Bob H.
The price is CA $414
CA $598 total
includes taxes & fees
Nov 17 - Nov 18
Fabulous 5-bedroom house with AC in charming Annapolis
A house with a yellow door and a window with a lamp outside.

13. 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.
The price is CA $190
CA $449 total
includes taxes & fees
Nov 15 - Nov 16
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A spacious living room with a high ceiling, large windows, and a ceiling fan.

14. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
The price is CA $378
CA $580 total
includes taxes & fees
Nov 10 - Nov 11
The Harness Creek Retreat in Annapolis
A spacious living room with a sofa set, a coffee table, and a chair. There is a painting on the wall and a window providing natural light.

15. Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher | 3BR | Near Waterfront
Edgewater
7.0 out of 10, Good, (2 reviews)
"The house was much smaller then it originally appeared to be in the listing photos and what they had available was the bare minimum. The neighborhood was rowdy and there was screaming late into the night. The shower also sprayed water all over the floor and caused a massive puddle. The house was overall nice and clean but not worth the price that it was listed for. A hotel would have much better accommodated our needs. "
United States
rebekah h.
The price is CA $404
CA $1,023 total
includes taxes & fees
Dec 8 - Dec 9
Londontowne Rancher | 3BR | Near Waterfront
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is CA $119
CA $392 total
includes taxes & fees
Nov 10 - Nov 11
Charming Coastal/Country Home w/3 Acres & Sauna!
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

17. 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
10.0 out of 10, Exceptional, (1 review)
"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...
United States
Amelia
The price is CA $254
CA $617 total
includes taxes & fees
Nov 13 - Nov 14
3-bedroom house in Deale located on Bay many amenities and great views
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

18. Relax on Kent Island in 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is CA $195
CA $481 total
includes taxes & fees
Nov 23 - Nov 24
Relax on Kent Island in 4 Bedroom Home w/Waterview
A backyard patio with a round table and chairs, surrounded by a gravel area.

19. 5 bedroom house with EV charger Near Downtown Annapolis

5 bedroom house with EV charger Near Downtown Annapolis
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"In town for a regatta, exactly what we required. "
United States
Jacob V.
The price is CA $477
CA $859 total
includes taxes & fees
Nov 15 - Nov 16
5 bedroom house with EV charger Near Downtown Annapolis
A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

20. Dean Street's Lower Deck House!

Dean Street's Lower Deck House!
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. "
United States
Nathaniel R.
The price is CA $314
CA $647 total
includes taxes & fees
Nov 10 - Nov 11
Dean Street's Lower Deck House!
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.
View all properties

Find vacation rentals that suit your style

Apartment image
Apartments
Apartments
apart-hotel image
Aparthotels
Aparthotels

Top Selby-on-the-Bay Hotel Reviews

A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater

10/10 Excellent

Clean. Very nice. Courteous staff.
Canada
karen
Reviewed November 11, 2025
Sonesta ES Suites Annapolis

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, 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 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Selby-on-the-Bay vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Selby-on-the-Bay vacation rentals we have selected for you start as low as CA $118 per night. Entering your travel dates in the search wizard 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?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This vacation home rental near Selby-on-the-Bay is located near the beach and has a fireplace, a balcony, 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. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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

Expedia has 5 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.