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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Cottages in Chester

The Heron's Nest at Atlantic Marina
Exterior

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (292)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (211)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
View from property

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (45)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (182)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
The Yellow Cottage on Harness Creek
Smart TV, DVD player, books

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (159)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Property grounds

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (6)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Secluded Cozy Cottage in Historic Downtown
Terrace/patio

Secluded Cozy Cottage in Historic Downtown

9.8 out of 10, Exceptional, (11)
"Perfect little cottage for 4 adults and an infant. Loved its location! "
The price is SAR 1,875
SAR 3,031 total
includes taxes & fees
6 Jul - 7 Jul
Secluded Cozy Cottage in Historic Downtown
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Marina

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (119)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Peaceful getaway convenient to local amenities including beach, boating & food
Beach towels

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (112)
"Great location and local restaurants. Perfect side for small group to do paper crafting. Would definitely book this place again. "
Peaceful getaway convenient to local amenities including beach, boating & food
Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly
On the beach, sun loungers, beach towels

Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly

10.0 out of 10, Exceptional, (31)
"Really like this place "
Water taxi just mins to Downtown Annapolis from waterfront home with a beach, dog-friendly
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Terrace/patio

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

10.0 out of 10, Exceptional, (27)
"Great location and very clean property. Cyndi was responsive and a great host. Would definitely stay again."
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Rock Creek Cottage, Waterfront, Serene Views
Fridge, microwave, oven, stovetop

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (3)
"My husband and I enjoyed our stay. The property was actually quite beautiful. The view was lovely as the home sits on a creek. The home provided everything we needed. Shopping and restaurants were very close. If you need to be in the Baltimore/Annapolis area as we had, this property is perfect."
Rock Creek Cottage, Waterfront, Serene Views
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun loungers, beach towels

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (99)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Perfect location for USNA Commissioning Week
View from property

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (82)
"Nice small property. Great for get aways and amazing service."
Perfect location for USNA Commissioning Week
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Miscellaneous

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (11)
"The home was so well appointed and walking distance to stores, restaurants, quaint museums and beautiful nature. The host was so friendly and helpful with quick responses. We had high winds and lots of rain, but stayed cozy and warm. What a friendly Island of people!!"
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

9.6 out of 10, Exceptional, (139)
"A lovely cottage to stay in. Lots of old world charm and location is unbeatable when want to stay in St. Michaels"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Cottage at Goose Neck Point
Sun loungers, beach towels

Cottage at Goose Neck Point

10.0 out of 10, Exceptional, (35)
"Wonderful hosts, great before and during stay communication, very friendly and welcoming. Cottage was cozy, well appointed and had the best view from the screened porch for morning coffees and evening glasses of wine!"
Cottage at Goose Neck Point
Chesapeake Cottage
1 bedroom, iron/ironing board, WiFi, bed sheets

Chesapeake Cottage

Chesapeake Cottage
Charming Waterfront Cottage Retreat near St. Michaels
Fridge, microwave, oven, stovetop

Charming Waterfront Cottage Retreat near St. Michaels

10.0 out of 10, Exceptional, (6)
"Our stay at this beautiful cottage was truly unforgettable! The space was clean, cozy, and well-appointed, with every detail carefully considered. Nestled right on the water’s edge, every inch of the house was tastefully decorated and had all the amenities you could ask for. The tasteful decor, fully stocked kitchen, and comfortable bed made us feel right at home from the moment we arrived.The hosts went above and beyond to make this an enjoyable stay, with excellent communication and thoughtful...
Charming Waterfront Cottage Retreat near St. Michaels
House w/Water Views of Rock Creek 2BA 2BA Cottage
Terrace/patio

House w/Water Views of Rock Creek 2BA 2BA Cottage

10.0 out of 10, Exceptional, (28)
"The house is nice, open & very clean. The host is great with communication & very responsive. The street is really quiet which was great for us, we were just hanging out for the weekend & checking out Annapolis for something to do. Great place for two couples or a small friend group!!"
House w/Water Views of Rock Creek 2BA 2BA Cottage
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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Frequently asked questions

How much do cottages in Chester cost?
Rates for cottages in Chester range between SAR 1,875 and SAR 1,875 per night. No matter your budget, you'll find the ideal place to reconnect with nature. These prices were 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.
Why book your cottage in Chester with Expedia?
We think that vacays should be a piece of cake, so if you're in search of cottages in Chester at a great price, Expedia is here to help. Keep the budget in check and go for a wallet-friendly option far from the hustle and bustle, or book a 5-star cottage to spoil the ones you love most.
How can I find cheap cottages in Chester?
With Expedia's handy filter tool, getting your hands on cheap cottages in Chester is easy. To view properties that are very pocket friendly, refine your search results by star rating, amenities and budget.