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Compare 35 Cottages in Chesapeake Bay with updated reviews, rates, and availability.

Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, (223)
"It looked just like the pictures. Property was spotless. Staff was friendly!"
The price is $175
$197 total
includes taxes & fees
May 2 - May 3
Key West Cottages
Small cottage for those little getaways
10.0 out of 10, Exceptional, (89)
"Enjoyed our time great bang for the buck."
Small cottage for those little getaways
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
9.8 out of 10, Exceptional, (257)
"We loved the location of this Cottage! We had a wonderful stay and we will definitely be back! This property had everything we needed and the owner was very accommodating."
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
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Norfolk Beach Cottage Rental
9.0 out of 10, Wonderful, (225)
"What a lovely home. Great for the whole family. Hosts were wonderful at communication with us throughout the weekend. Loved how close the beach was an easy to get to lots of restaurants etc. Kitchen was well stocked and plenty of seating in the dining room and comfy living area. I hope we can return if my daughter goes to ODU"
The price is $199
$396 total
includes taxes & fees
May 2 - May 3
Norfolk Beach Cottage Rental
Cozy Little Cottage on chincoteague island va.
9.8 out of 10, Exceptional, (16)
"This was our second time staying here, with our first being during the summer. The cottage is very clean and overall quite pleasant with a location perfect for bicycling into town and to the beach. However, this cottage really needs heat if it is to be rented during the cooler months. The owner did provide a portable heater at our request, which did warm the place, but was very noisy. Would stay again but only in the warmer weather. "
Cozy Little Cottage on chincoteague island va.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (106)
"Wonderful return visit to St Michaels. This time at a fantastic historical home in perfect location. Home was everything you could ask for and more. Park your car and walk anywhere, within a very quiet neighborhood, yet minutes from all St Michaels offers. Highly recommend this Property and host."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Mermaid's and Mutts Retreat
9.2 out of 10, Wonderful, (22)
"Clean, nice layout. Close enough to downtown & other sights"
Mermaid's and Mutts Retreat
Cozy island cottage with a Key West flair - CLOSEST TO THE BEACH!!!
10.0 out of 10, Exceptional, (96)
"Was welcoming from the time you drove up. This place was very clean, very well thought out, and we highly recommend. If you are wanting a clean spot, time to relax, and a place to make memories this is the one for you!"
Cozy island cottage with a Key West flair - CLOSEST TO THE BEACH!!!
Newly renovated water view cottage nestled in the pines.
10.0 out of 10, Exceptional, (80)
"This is a great cottage for a weekend stay!"
Newly renovated water view cottage nestled in the pines.
Beachfront paradise, relaxed, pet friendly
9.8 out of 10, Exceptional, (8)
"Great location. Small but perfect for close friends and family. Water heaters are small but manageable with quick showers. Overall a great place to stay and great communication with property owners. Would and will definitely stay again."
Beachfront paradise, relaxed, pet friendly
Manor and Mutts #2 (3-Bedroom Cottage) - Pets Allowed by RedAwning
9.4 out of 10, Exceptional, (3)
"Just like thay stated. A dual family under renovation. If you want shiny granite and huge bathrooms you won't be happy. Larger than expected. Highly recommend this place if coming to visit family at Norfork Naval Base. Close to the base, beautiful beach. Kitchen is workable. Wish they had a few more drinking glasses and a can opener but stores were very close by and we were able to pick some up."
Manor and Mutts #2 (3-Bedroom Cottage) - Pets Allowed by RedAwning
Cottage On Famous Chincoteague Island-Famous Wild Ponies
9.8 out of 10, Exceptional, (53)
"This property had a plumbing issue at the time we were to be there. Christine moved us to another property, oyster haven. She couldnt have been nicer to accommodate us. Cute place! Convenient as well."
Cottage On Famous Chincoteague Island-Famous Wild Ponies
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (103)
"Really enjoyed the house and it’s location, perfect for a couples weekend!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
SeaLaVie!!!
10.0 out of 10, Exceptional, (20)
"Great little place. Everything we needed for a weekend getaway!"
SeaLaVie!!!
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, (151)
"Quaint yet period correct. Plenty of room with decent kitchen. Especially love location and screaned back porch. Have stayed in house several times and does not disappoint!! Will go again for sure!"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath
8.4 out of 10, Very Good, (37)
"The ceiling was low, bathroom sink was clogged. Bathroom floor needs work. Property was clean and beds were comfortable. Loved being at the beach. They have a different Property i stayed at on an earlier date that was great. Although we didnt care for the mentioned things, the process was easy and the owners were good to deal with."
The price is $179
$356 total
includes taxes & fees
May 2 - May 3
Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath
Cozy Cottage of Alexandria Privacy Parking Metro Full Kitchen Laundry Patio WiFi
9.6 out of 10, Exceptional, (170)
"Property and house was in a great neighborhood and very comfortable"
Cozy Cottage of Alexandria Privacy Parking Metro Full Kitchen Laundry Patio WiFi
The Hideaway Cottage
10.0 out of 10, Exceptional, (68)
"Enjoy Don's cottage - the screened in patio was lovely to enjoy coffee and do some light office work. Kitchen had enough of everything to heat or prepare simple meals. Hot water was plentiful and pressure good in the shower. Bed was comfortable. The area is very quiet at night but during the day there is a small business next door that you do hear light people chatter/deliveries. I would say this location is like a modern cabin - just enough of everything but still feels rustic."
The Hideaway Cottage
Cozy 3-bedroom cottage - fenced yard, 4 TVs, dogs OK, W/D
10.0 out of 10, Exceptional, (18)
"This is a GREAT house with awesome owners. We were in Norfolk to visit family, very cute home with a really good floor plan and fenced backyard. Nice, quiet neighborhood and close to everything we needed, we will definitely be back!"
Cozy 3-bedroom cottage - fenced yard, 4 TVs, dogs OK, W/D
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (63)
"My husband and I stayed at the Weems creek cottage for a childless getaway weekend. Everything was excellent, from communication with Jim, to the gorgeous property and the time we had in the city of Annapolis. Not to mention the weather was nice! We spent Friday and most of Saturday in the city of Annapolis. On Saturday evening we just enjoyed our stay at the cottage, we had two fires, relaxing in the Adirondack chairs overlooking the water. THIS was exactly what we needed and what we enjoy...
Amazing views, short walks to great dining!
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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.

Other property types in Chesapeake Bay

Holiday Inn Washington Capitol - Natl Mall, an IHG Hotel
3.0 star property
8.4 out of 10, Very Good, (3674)
"Was exactly what I needed for an active, recreational trip. Good staff and housekeeping. AC was noisy but everything else was very good. "
The price is $160
$186 total
includes taxes & fees
May 27 - May 28
Holiday Inn Washington Capitol - Natl Mall, an IHG Hotel
Glover Park - Georgetown
4.0 star property
8.8 out of 10, Excellent, (1985)
"I stayed for 3 days, never had housekeeping come. I asked for towel, the man had an attitude with me. Otherwise the place was great. I always tip housekeeping, not this time"
The price is $183
$213 total
includes taxes & fees
May 26 - May 27
Glover Park - Georgetown
The Dupont Circle Hotel
4.5 star property
9.4 out of 10, Exceptional, (1192)
"The staff was excellent and catered to our every need. Without a doubt we would stay there again in a heartbeat. They made every effort make us feel special. "
The price is $275
$319 total
includes taxes & fees
May 3 - May 4
The Dupont Circle Hotel
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.

Chesapeake Bay Cottages information

Number of reviews
1,653
Accommodation
35 Cottages
Lowest Price
$175
Highest Price
$199

Frequently asked questions

How much do cottages in Chesapeake Bay cost?
You’ll pay between $175 and $199 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 35 cottages in Chesapeake Bay and then choose your favorite. Whether you’re embarking on a family vacation or a break with pals, your ideal stay is just clicks away with Expedia.
Why book your cottage in Chesapeake Bay with Expedia?
Reserving a cottage in Chesapeake Bay is as simple as working out your travel dates and selecting an ideal place for outdoor fun and relaxation. From chic retreats to affordable properties and cottages that include perks like a hot tub, Expedia has something for all traveler styles. As for awesome deals? We’ve got them as well!
How can I find cheap cottages in Chesapeake Bay?
A wonderful way to compare cheap cottages in Chesapeake Bay is with Expedia’s convenient filter tool. Fine-tune your search results by star rating, budget and amenities to discover unbeatable bargains in just a few clicks.
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.

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