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Check prices for these dates

Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct

Featured Cottages in Chesapeake Bay

Our top choices for Chesapeake Bay cottages

Key West Cottages
Exterior

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (437)
"Great place to stay!"
Key West Cottages
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
On the beach

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

9.6 out of 10, Exceptional, (4)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is AU$465
includes taxes & fees
3 Sept - 4 Sept
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
House (3 Bedrooms) | Front of property

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
The price is AU$728
includes taxes & fees
1 Sept - 2 Sept
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Soul Oasis - home on the Chesapeake Bay
Sun-loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (31)
"The A-frame cottage was clean and comfortable. I was accompanied by my son and two grandchildren (ages 12 and 14), and we really loved it. We went fishing in bay at the beach area below the cottage, and also did a lot of fossil hunting along the cliffs, which are breathtaking. Our host Teresa was extremely helpful and welcoming. We will definitely be going back!"
The price is AU$472
includes taxes & fees
23 Sept - 24 Sept
Soul Oasis - home on the Chesapeake Bay
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Fridge, microwave, oven, stovetop

Comfortable & Private 2 Bedrm Cottage w/ King bed.

10.0 out of 10, Exceptional, (13)
"It was a great stay. Was there for work. Close for work and close to the beach. "
The price is AU$551
includes taxes & fees
8 Sept - 9 Sept
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
Property grounds

Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

10.0 out of 10, Exceptional, (16)
"Hubs and I were looking for a relaxing getaway and boy did we find it. This cottage was perfect. "
The price is AU$421
includes taxes & fees
1 Sept - 2 Sept
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
Cozy Bay Cottage private backyard blocks from beach!
Dining

Cozy Bay Cottage private backyard blocks from beach!

9.0 out of 10, Wonderful, (38)
"Clean and up-to-date home. Close to the beach. Convenient and comfortable. Would rent again. "
The price is AU$668
includes taxes & fees
1 Sept - 2 Sept
Cozy Bay Cottage private backyard blocks from beach!
Bay Dream Believer Cottage on Beautiful East River Waterfront
Exterior

Bay Dream Believer Cottage on Beautiful East River Waterfront

2.0 star property
10.0 out of 10, Exceptional, (19)
"Wonderful location, host communicated well"
The price is AU$715
includes taxes & fees
28 Aug - 29 Aug
Bay Dream Believer Cottage on Beautiful East River Waterfront
Cottage Located on the Patuxent River!
Sun-loungers

Cottage Located on the Patuxent River!

10.0 out of 10, Exceptional, (40)
"The accommodations were superb and being on the water was amazing!"
The price is AU$567
includes taxes & fees
7 Sept - 8 Sept
Cottage Located on the Patuxent River!
Deal Island Bay Cottage
Fridge, microwave, oven, stovetop

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (57)
"We got every year and stay here, it’s great! "
The price is AU$428
includes taxes & fees
26 Sept - 27 Sept
Deal Island Bay Cottage
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Smart TV, books

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

9.6 out of 10, Exceptional, (4)
"The house was close to family in the area, so location was great. The house was clean and airy. The door lock was a bit tricky - otherwise all was excellent."
The price is AU$540
includes taxes & fees
23 Sept - 24 Sept
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Norfolk Beach Cottage Rental
Fridge, microwave, oven, stovetop

Norfolk Beach Cottage Rental

9.0 out of 10, Wonderful, (271)
"Cute & comfy place that was perfect for my kids, husband & I. We went to a concert & Ive never stayed in this part of Norfolk. Great location & exactly what we were looking for!"
The price is AU$645
includes taxes & fees
16 Sept - 17 Sept
Norfolk Beach Cottage Rental
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
Fridge, microwave, stovetop, dishwasher

Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town

10.0 out of 10, Exceptional, (20)
"We were very pleased with the location including its proximity to the sites and the neighborhood. Fran was very kind and responsive during our stay. "
The price is AU$508
includes taxes & fees
1 Sept - 2 Sept
Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
Interior

Cottage w Private Creek, Sunroom, Fire Pit, & WiFi

9.4 out of 10, Exceptional, (133)
"Awesome two night stay! Highly recommend! "
The price is AU$778
includes taxes & fees
17 Sept - 18 Sept
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
Grandma’s Cottage will wrap around you like a warm hug
Terrace/patio

Grandma’s Cottage will wrap around you like a warm hug

The price is AU$651
includes taxes & fees
10 Sept - 11 Sept
Grandma’s Cottage will wrap around you like a warm hug
Cottage - Williamsburg Pet-Friendly Getaway – Heated Pool, Free Game Room, Near Parks
Outdoor dining

Cottage - Williamsburg Pet-Friendly Getaway – Heated Pool, Free Game Room, Near Parks

9.8 out of 10, Exceptional, (14)
"It was a great stay! We really enjoyed the cabin! The area was nice and everyone was very friendly. We would definitely stay again!"
The price is AU$419
includes taxes & fees
28 Aug - 29 Aug
Cottage - Williamsburg Pet-Friendly Getaway – Heated Pool, Free Game Room, Near Parks
Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
Interior

Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown

8.0 out of 10, Very good, (4)
"Host was super responsive and available. Location is excellent - close to boat and kayak launch. Grill, smoker, patio were all great. "
The price is AU$1,934
includes taxes & fees
4 Sept - 5 Sept
Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Property grounds

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is AU$1,034
includes taxes & fees
1 Sept - 2 Sept
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Secluded Cozy Cottage in Historic Downtown
Exterior detail

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (13)
"We had a very lovely stay . This is an excellent location . "
The price is AU$1,244
includes taxes & fees
7 Sept - 8 Sept
Secluded Cozy Cottage in Historic Downtown
6 Mi to Salisbury: Forest-view Sanctuary!
House (3 Bedrooms) | Front of property

6 Mi to Salisbury: Forest-view Sanctuary!

3.0 star property
The price is AU$367
includes taxes & fees
28 Aug - 29 Aug
6 Mi to Salisbury: Forest-view Sanctuary!
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 Bay Hotel Reviews

Find out more about Chesapeake Bay

Find out more about Chesapeake Bay

Chesapeake Bay Cottages information

Number of reviews
1,695
Accommodation
80 Cottages
Lowest Price
AU$419
Highest Price
AU$1,244

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

How much do cottages in Chesapeake Bay cost?
You'll pay between AU$419 and AU$1,244 per night for cottages in Chesapeake Bay. No matter your budget, an excellent stay is only clicks away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Chesapeake Bay?
Browse through our 80 cottages in Chesapeake Bay and then choose your favourite. Whether you're embarking on a family holiday or a break with pals, your ideal stay is just clicks away with Expedia.
What is there to do in Chesapeake Bay near my cottage?
Whether you're interested in history, food, shopping or sightseeing, Chesapeake Bay is one place you'll never get bored! The awesome city of Washington has plenty of things to do and see, including National Mall, Smithsonian Institution and National Museum of African American History and Culture. If you're headed to Baltimore, National Aquarium in Baltimore, Baltimore Museum of Art and American Visionary Art Museum are must-do's.