Apartment
8.0(231 Reviews)
25 Bedrooms
58 Guests
Breakfast
Balcony/Terrace
View
Kitchen
US $224/Night
Chesapeake Bay stays by Sonder
Across Chesapeake Bay, evenings in town linger well past dinner.
Sonder Chesapeake Bay Places to Stay
Chesapeake Bay moves between Baltimore rowhouses, Annapolis harbor streets, and Norfolk day trips, with city weekends shaped by waterfront dining, museums, and transit-friendly neighborhoods. Start where your plans point, then find Sonder apartment-style stays and boutique hotels close to the places you came for.
Regions of Chesapeake Bay
Corners of Chesapeake Bay worth settling into.
Every region keeps its own pace. Browse the areas of Chesapeake Bay where Sonder has stays, then narrow down to the city you want to wake up in.
Chesapeake Bay city stays
Bay cities, downtown lights, neighborhood morning rhythm.
From Baltimore’s city streets to Annapolis’s historic core and Norfolk’s downtown pace, start with the place that puts you closest to the Chesapeake Bay you came for.
Chesapeake Bay by stay type
Find the right kind of stay.
From boutique hotels in the middle of everything to apartment-style stays built for settling in, browse Chesapeake Bay by the kind of place that fits your trip.
Chesapeake Bay stays
8.0
9.6
9.7
10.0
9.0
10.0
10.0
9.8
9.0
9.8
9.0
9.2
8.4
8.6
9.2
8.5
8.4
8.6
8.8
Rooms for city stays across Chesapeake Bay.
A curated edit of apartment-style stays and boutique hotels across Chesapeake Bay, so you can see the range before you narrow down.
8.0
Condo
9.6(29 Reviews)
1 Bedroom
Oceanfront
Hot Tub
Parking
Ocean View
US $322/Night
Apartment
9.7(3 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- View
Air Conditioner
US $343/Night
Apartment
10.0(1 Review)
2 Bedrooms
5 Guests
- Kitchen
- Air Conditioner
Internet
Wheelchair Accessible
US $295/Night
Apartment
9.0(2 Reviews)
3 Bedrooms
6 Guests
- Parking
- Air Conditioner
- Internet
Child Friendly
US $624/Night
Apartment
10.0(3 Reviews)
2 Bedrooms
5 Guests
- Kitchen
- Air Conditioner
- Internet
- Wheelchair Accessible
US $301/Night
Apartment
10.0(2 Reviews)
1 Bedroom
4 Guests
- Air Conditioner
- Internet
- Child Friendly
Security/Safety
US $234/Night
Apartment
9.8(20 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $298/Night
Hotel
9.0(36 Reviews)
- Breakfast
- Balcony/Terrace
- View
- Kitchen
US $381/Night
Apartment
9.8(6 Reviews)
2 Bedrooms
5 Guests
- Parking
Pool- Balcony/Terrace
- Kitchen
US $362/Night
Apartment
9.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $213/Night
Condo
9.2(50 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $403/Night
Aparthotels in Chesapeake Bay
Over 122+ Apartment-Style Stays with Hotel Comfort in Chesapeake Bay
Hotel
8.4(87 Reviews)
- Parking
- Kitchen
- Air Conditioner
- Internet
US $135/Night
US $133/Night
Hotel
8.6(344 Reviews)
- Breakfast
EV Charge Station- Parking
- Kitchen
US $164/Night
US $291/Night
US $131/Night
Hotel
9.2(366 Reviews)
- Oceanfront
- Parking
Spa- Ocean View
US $316/Night
Hotel
8.5(76 Reviews)
Private Pool- Hot Tub
- Parking
- Pool
US $157/Night
US $172/Night
Hotel
8.4(18 Reviews)
- Breakfast
- EV Charge Station
- Parking
- Kitchen
US $178/Night
Hotel
8.6(498 Reviews)
- Breakfast
- EV Charge Station
- Parking
- Balcony/Terrace
US $167/Night
US $550/Night
Hotel
8.8(35 Reviews)
- Private Pool
- Oceanfront
- Breakfast
- EV Charge Station
US $141/Night
Good to know
Chesapeake Bay travel questions, answered.
Quick answers to the questions travelers ask most.
01 / 07
What are the top Boutique Hotels and Aparthotels in Chesapeake Bay?
Discover top family-friendly travel options in or near Chesapeake Bay. If you're planning a trip or vacation to Chesapeake Bay, consider spending a week or two at any of our welcoming family-allowed hotels, resorts, or other recommended properties. These are renowned as the Top Vacation Rentals and Places to Stay in Chesapeake Bay:
- Huge Studio w Full Kitchen W D Parking
- Exclusive Apt in Shaw
- Cozy 3 Bedroom Min to National Mall Great Location and Free Parking
- Rock Creek Park Residence
- The Chelsea - King 1BR in Rosslyn with Queen Sleeper, Free Parking & Metro Access
- Luxury 3-BR - Parking - EV Charger - Walk to Metro
- 2BR Luxury City Suite With Gym & Pool
- On DCs Doorstep Family Friendly 2 bed Cap Hill Apt - Permit
- Urban 2BR Oasis with Scenic Rooftop and Gym
- Capital Hill 1 Charming Oasis in Downtown DC near Metro with Rooftop View and Free WIFI
02 / 07
How many Boutique Hotels, Aparthotels, and Urban Apartments are available in Chesapeake Bay?
Sonder™ regularly updates its listings to offer a diverse selection of accommodations, each with clear details on family amenities. Currently, there are over 680 active properties listed by Sonder in 2026 in the Chesapeake Bay area, with new additions daily. By aggregating listings from various websites and travel providers, Sonder delivers a vast array of top places to stay that are perfect for families visiting Chesapeake Bay.
03 / 07
Which type of Chesapeake Bay stay works best if I want to walk to food and daily errands?
Choose a stay in the most walkable city center if you want cafes, groceries, and casual dining within easy reach. That usually suits short trips and car-light plans. Check the listing map and neighborhood notes for exact walkability, since access can vary by building.
04 / 07
What kind of Chesapeake Bay stay makes the most sense for a weekend trip?
Pick a centrally located stay if you want a weekend that feels easy from arrival to checkout. You will spend less time coordinating transit and more time exploring on foot. Review the listing for nearby transit, parking, and neighborhood access before you book.
05 / 07
Is Chesapeake Bay a good fit for a longer stay or remote work trip?
Choose an apartment-style stay if you are planning several nights or working remotely. A separate living area, workspace, and kitchen can make the rhythm feel more practical. Since amenities vary, confirm workspace, WiFi, and laundry details in the listing.
06 / 07
When is the best time to book a stay in Chesapeake Bay?
Book early for the dates when you want the calmest planning and the broadest choice of stays. If you prefer easier pacing, aim for shoulder periods rather than peak travel windows. Exact seasonality depends on the city and building, so check the listing notes.
07 / 07
How should I plan getting around between cities in Chesapeake Bay?
Plan on using a car or a mix of driving and local transit if you want to move between cities with less hassle. A walkable central stay works well once you arrive, but intercity travel is easier to manage when you confirm the location and parking details first.
Discover top family-friendly travel options in or near Chesapeake Bay. If you're planning a trip or vacation to Chesapeake Bay, consider spending a week or two at any of our welcoming family-allowed hotels, resorts, or other recommended properties. These are renowned as the Top Vacation Rentals and Places to Stay in Chesapeake Bay:
- Huge Studio w Full Kitchen W D Parking
- Exclusive Apt in Shaw
- Cozy 3 Bedroom Min to National Mall Great Location and Free Parking
- Rock Creek Park Residence
- The Chelsea - King 1BR in Rosslyn with Queen Sleeper, Free Parking & Metro Access
- Luxury 3-BR - Parking - EV Charger - Walk to Metro
- 2BR Luxury City Suite With Gym & Pool
- On DCs Doorstep Family Friendly 2 bed Cap Hill Apt - Permit
- Urban 2BR Oasis with Scenic Rooftop and Gym
- Capital Hill 1 Charming Oasis in Downtown DC near Metro with Rooftop View and Free WIFI
Sonder™ regularly updates its listings to offer a diverse selection of accommodations, each with clear details on family amenities. Currently, there are over 680 active properties listed by Sonder in 2026 in the Chesapeake Bay area, with new additions daily. By aggregating listings from various websites and travel providers, Sonder delivers a vast array of top places to stay that are perfect for families visiting Chesapeake Bay.
Choose a stay in the most walkable city center if you want cafes, groceries, and casual dining within easy reach. That usually suits short trips and car-light plans. Check the listing map and neighborhood notes for exact walkability, since access can vary by building.
Pick a centrally located stay if you want a weekend that feels easy from arrival to checkout. You will spend less time coordinating transit and more time exploring on foot. Review the listing for nearby transit, parking, and neighborhood access before you book.
Choose an apartment-style stay if you are planning several nights or working remotely. A separate living area, workspace, and kitchen can make the rhythm feel more practical. Since amenities vary, confirm workspace, WiFi, and laundry details in the listing.
Book early for the dates when you want the calmest planning and the broadest choice of stays. If you prefer easier pacing, aim for shoulder periods rather than peak travel windows. Exact seasonality depends on the city and building, so check the listing notes.
Plan on using a car or a mix of driving and local transit if you want to move between cities with less hassle. A walkable central stay works well once you arrive, but intercity travel is easier to manage when you confirm the location and parking details first.
