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Browse Select Chesapeake Beach Apartments

Our top choices for Chesapeake Beach apartments

Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops
Iron/ironing board, WiFi, bed sheets

Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops

10.0 out of 10, Exceptional, (22)
"Stayed for the weekend- parked the car and could walk to everything- perfect. Host was super responsive and the place was super clean!"
Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops
Harbor View Suite
Fridge, microwave, coffee/tea maker, toaster

Harbor View Suite

10.0 out of 10, Exceptional, (26)
"The room and location were perfect. Very clean and comfortable space to stay and right in the heart of town. "
Harbor View Suite
Guest Quarters at the Inn - 103
Iron/ironing board, free WiFi, bed sheets

Guest Quarters at the Inn - 103

9.6 out of 10, Exceptional, (24)
"Very nice room with good accessibility for someone with limited mobility. The room description in Expedia was completely accurate, and we loved the accessibility features. The location is very close to good restaurants that also have good accessibility."
Guest Quarters at the Inn - 103
Guest quarters at the inn - 204
1 bedroom, iron/ironing board, free WiFi, bed sheets

Guest quarters at the inn - 204

9.8 out of 10, Exceptional, (14)
"Loved the place! Plenty of room. Hubby and I snuggled in the comfy robes most of the time! Only thing I’d recommend is WiFi for tvs so visitors can log on to their personal streaming apps. "
Guest quarters at the inn - 204
Guest quarters at the inn - 205
TV

Guest quarters at the inn - 205

9.2 out of 10, Wonderful, (15)
"Great stay"
Guest quarters at the inn - 205
Chesapeake Bayside Loft
Property grounds

Chesapeake Bayside Loft

8.0 out of 10, Very good, (12)
"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."
Chesapeake Bayside Loft
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Exterior

Modern Flat in the Heart of St. Michaels – Walk Everywhere

10.0 out of 10, Exceptional, (47)
"Beautiful, clean and well appointed in the perfect spot in downtown Saint Michael’s. Highly recommended!!"
Modern Flat in the Heart of St. Michaels – Walk Everywhere
1 Mi to Boardwalk: Convenient North Beach Apt!
Apartment (1 Bedroom) | Interior

1 Mi to Boardwalk: Convenient North Beach Apt!

3.0 star property
1 Mi to Boardwalk: Convenient North Beach Apt!
Elegant 2-Bedroom Retreat in Historic Saint Michaels – Walk to Dining & Shops
Living area

Elegant 2-Bedroom Retreat in Historic Saint Michaels – Walk to Dining & Shops

9.8 out of 10, Exceptional, (6)
"We loved the property and the location (can’t be beat!). We walked to shops, restaurants, and bars all over town. It also had convenient parking. The apartment was clean and had everything we needed for a short stay. "
Elegant 2-Bedroom Retreat in Historic Saint Michaels – Walk to Dining & Shops
Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
Property grounds

Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!

10.0 out of 10, Exceptional, (32)
"Our plans changed last minute and Pam was extremely accommodating. Very thankful for her flexibility "
Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
Terrace Suite · Terrace Suite - Private Flat in Historic Manor.
TV

Terrace Suite · Terrace Suite - Private Flat in Historic Manor.

9.8 out of 10, Exceptional, (31)
"Great stay, clean & owner gave great local suggestions!"
Terrace Suite · Terrace Suite - Private Flat in Historic Manor.
1 Mi to Boardwalk: Convenient North Beach Apt!
Beach

1 Mi to Boardwalk: Convenient North Beach Apt!

8.0 out of 10, Very good, (1)
"It's a good location, easy drive to the beach and pier, on a dead-end street in a quiet neighborhood. New interior finishes, so like-new condition. Approach is a little tricky... you have to walk down a small grassy embankment to get to the entry door (rear of the building), which wasn't obvious at first but owner answered our call and us direction. Not a destination-kind-of-stay but perfectly adequate for a place to shower and sleep. Has a small deck with a garden hose to wash the sand off. "
1 Mi to Boardwalk: Convenient North Beach Apt!
Guest Quarters at the Inn - 101
Iron/ironing board, free WiFi, bed sheets

Guest Quarters at the Inn - 101

9.6 out of 10, Exceptional, (15)
"Very nice place. Will stay there again. "
Guest Quarters at the Inn - 101
Relax & Recharge in Our Family-Favorite Retreat
Property grounds

Relax & Recharge in Our Family-Favorite Retreat

2.0 out of 10, (1)
"Was never able to actually stay here because the owner never provided check-in info. They didn't respond to messages on the app or calling their personal number directly, didn’t respond to Vrbo employees either when they tried to contact the owner. Had to get a hotel last-minute after giving them three hours past the scheduled check-in time to respond. Incredibly frustrating and inconvenient as I was looking for somewhere to stay with my infant daughter after our house was packed up as we're...
Relax & Recharge in Our Family-Favorite Retreat
Courtyard Studio at Bancroft Manor. Cozy Retreat!
Exterior

Courtyard Studio at Bancroft Manor. Cozy Retreat!

10.0 out of 10, Exceptional, (23)
"Needed a place to stay before I move to SC and this place/location was perfect! Great all around and great communication."
Courtyard Studio at Bancroft Manor. Cozy Retreat!
Studio on the Bay.
Beach nearby, beach towels

Studio on the Bay.

10.0 out of 10, Exceptional, (22)
"Everything was fantastic! Clean, well stocked with essentials, and close to the beach. Quiet neighborhood and only 15-20 minutes from many state parks. Great communication from the host throughout our stay. We will be visiting again!"
Studio on the Bay.
Bay View Studio Apartment
Outdoor spa tub

Bay View Studio Apartment

10.0 out of 10, Exceptional, (50)
"Wonderful place to stay for a peaceful weekend. The hot tub was definitely a highlight. Everything was clean and as described. I would stay there again!"
Bay View Studio Apartment
New Loft w/South River view from treehouse deck!
Terrace/patio

New Loft w/South River view from treehouse deck!

10.0 out of 10, Exceptional, (22)
"Nice stay"
New Loft w/South River view from treehouse deck!
Guest Quarters at the Inn - 102
1 bedroom, iron/ironing board, free WiFi, bed sheets

Guest Quarters at the Inn - 102

9.8 out of 10, Exceptional, (19)
"Close to many restaurants and activities "
Guest Quarters at the Inn - 102
HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!
Property grounds

HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!

9.8 out of 10, Exceptional, (19)
"Beautiful veiw Nice neighborhood Great location away from downtown but still close Excellent host"
HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!
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 Chesapeake Beach Hotel Reviews

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Great place to stay"
Bradley 1-night trip
Posted 2 days ago
St Michaels Inn