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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Cottages in Chester

The Heron's Nest at Atlantic Marina
Terrace/patio

The Heron's Nest at Atlantic Marina

9.8 out of 10, Exceptional, (307)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (120)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Exterior

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

9.6 out of 10, Exceptional, (124)
"We had a wonderful stay. This was our second time staying here and we loved it. Very quay, cozy and clean. Everything as advertised. Location is perfect as it is a very walkable town. This place is right in the middle. The owner was very friendly, open and communicative. And I had a big surprise when we returned. My neck pillow I had forgotten and left it 2 years ago was still there sitting in a closet. We hope to return next year. "
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Exterior

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (105)
"Secluded"
Secluded Waterfront Cottage on 200 acre farm near Queenstown
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Exterior

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

10.0 out of 10, Exceptional, (11)
"We had a wonderful stay at the Point of a View Cottage! The views are spectacular and we also enjoyed how easy it was to walk to places to eat and the local market. Recommendations for places to eat were spot on and also appreciated a message over the weekend notifying us of the local craft market held Sunday morning. Would love to come again one day! "
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Peaceful getaway convenient to local amenities including beach, boating & food
Exterior

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

9.8 out of 10, Exceptional, (119)
"Great property to relax and stroll around town"
Peaceful getaway convenient to local amenities including beach, boating & food
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Outdoor dining

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is SAR 1,350
SAR 2,492 total
includes taxes & fees
6 Oct - 7 Oct
Chesapeake Cottages- 2 Quaint Waterfront Retreats
The Middle Point Cabin in Saint Michaels
Outdoor dining

The Middle Point Cabin in Saint Michaels

9.8 out of 10, Exceptional, (51)
"We had a great stay. The cottage is just like the pictures. Nice area…lots of things to do."
The Middle Point Cabin in Saint Michaels
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Exterior

Beachfront Home Minutes to Downtown Annapolis Dogs OK

9.8 out of 10, Exceptional, (37)
"We wanted to celebrate my wife’s birthday with some friends, and a bushel of crabs…and what an incredible house to host a special occasion. The kids had the water/mini beach and plenty of yard space to play; there was a space outside to eat the crabs; and the house was incredibly clean and inviting. "
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Chesapeake Cottage
Exterior

Chesapeake Cottage

10.0 out of 10, Exceptional, (4)
"Great place close to key locations on kent"
Chesapeake Cottage
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Property grounds

Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills

9.4 out of 10, Exceptional, (3)
"We had a great stay! Ryan was a great host, and the cottage was perfect for our needs. We would certainly stay here again."
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (234)
"We had a lovely stay here.Place was VERY clean.Visited St. Michael’s and relaxed on the porch & pier.It met our expectations."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Exterior

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

9.8 out of 10, Exceptional, (187)
"Excellent accommodations. Comfortable, good location.One way you could improve is to furnish wash cloths and hand towels. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Exterior

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

9.6 out of 10, Exceptional, (143)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Outdoor dining

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

10.0 out of 10, Exceptional, (218)
"We had a wonderful time. Hosts were very kind and responsive! Beautiful property "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Secluded Cozy Cottage in Historic Downtown
Exterior detail

Secluded Cozy Cottage in Historic Downtown

9.6 out of 10, Exceptional, (15)
"We had a very lovely stay . This is an excellent location . "
The price is SAR 1,688
SAR 2,809 total
includes taxes & fees
2 Nov - 3 Nov
Secluded Cozy Cottage in Historic Downtown
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Exterior

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

10.0 out of 10, Exceptional, (9)
"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
The Yellow Cottage on Harness Creek
Exterior

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (168)
"A lovely property in the perfect location! We will definitely rent again!"
The Yellow Cottage on Harness Creek
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Terrace/patio

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
The price is SAR 1,571
SAR 3,415 total
includes taxes & fees
1 Nov - 2 Nov
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!
Exterior

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!

10.0 out of 10, Exceptional, (97)
"Thanks for a great stay. The backyard was perfect for the whole family, and the house is lovely - clean, comfortable, and very well stocked! "
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!
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 Chester Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Great"
BRIAN 2-night trip
Posted 2 days ago
Hilton Garden Inn Annapolis Downtown

Frequently asked questions

How much do cottages in Chester cost?
Rates for cottages in Chester range between SAR 2,492 and SAR 3,415 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.