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Compare 61 Cottages in Chester with updated reviews, rates, and availability.

Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Cottage on a quite creek of the Chesapeake Bay with private pool.

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Front of house from St. Michaels harbor looking across Town Park

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

9.6 out of 10, Exceptional, (112)
"Our stay in St Michael's was wonderful. The location of this property could not be better. Close to marina, parks, restaurants, historic downtown and the maritime museum. We never needed to use our car! Tom is an excellent host. "
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Property grounds

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"We thoroughly enjoyed our long weekend stay. We spent great time together in the cozy and spacious living room, as well as enjoying the nice waterfront outdoor areas. The house is unique, well equipped, very clean, and with great attention to details in every room. Host was very proactive and responsive in the communication. Canoes and bikes are available, what we enjoyed. Views from the house were wonderful, including a beautiful sunrise. It was a very relaxing family weekend and we can’t wait...
The price is SAR 1,686
SAR 3,559 total
includes taxes & fees
23 Nov - 24 Nov
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
Exterior detail

Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,

10.0 out of 10, Exceptional, (80)
"My husband and son really loved their stay at Pat & Ken's VRBO house! They enjoyed going on walks around the neighborhood, visiting the local restaurants, and sitting in the hot tub. It was perfect for our family. Pat & Ken are such gracious hosts, and we will definitely stay here again!"
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

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

10.0 out of 10, Exceptional, (204)
"Very cozy and clean. Beautiful surroundings with direct view of the water. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Front and side of W Melson House

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

9.6 out of 10, Exceptional, (115)
"Waters edge is just a few steps away to sit and watch boats come in and out. So cute and the most amazing artifacts decorating the place made it even more captivating. Short walk to coffee, food and shopping local. The owner was responsive and kind as well as super easy to work with. Will definitely return."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
The Heron's Nest at Atlantic Marina
Family Room with Water View

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (286)
"We booked this property, along with the other property at the marina for our wedding weekend and WOW - we LOVED our stay. The views from this cute little cottage are phenomenal. We woke up each morning to watch the sunrise. The hosts were extremely accommodating and even helped secure our cake topper that we accidentally left behind in the whirlwind of check-out. This was the perfect spot for our first look as well. I would highly recommend booking this place for a cute romantic stay!"
The Heron's Nest at Atlantic Marina
Eastern Shore Waterside Cottage Near St. Michaels
wrap around porch with rockers and dining area

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Had a great visit. House was perfect and the area is absolutely gorgeous"
Eastern Shore Waterside Cottage Near St. Michaels
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Front and side view of Blades House from Locust St.

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

9.6 out of 10, Exceptional, (134)
"We loved this house, it was perfect for exploring town and as a base for things further afield. Comfortable, thoughtfully and well stocked with lots of charm."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Exterior

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

9.8 out of 10, Exceptional, (33)
"A beautiful stay on the Chesapeake."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
House w/Water Views of Rock Creek 2BA 2BA Cottage
Exterior detail

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

10.0 out of 10, Exceptional, (22)
"Very quiet street, our stay was relaxing and just what we needed! "
House w/Water Views of Rock Creek 2BA 2BA Cottage
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Blue heron sunset

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

10.0 out of 10, Exceptional, (7)
"“Point of View” waterfront cottage did not disappoint. In fact, it was beyond expectations. Maria’s (the host) personal touches made the cottage feel like home. We used “Point of View” as overflow for a family reunion we were having. It is perfectly situated for easy walking to anything you need or want to do on Tilghman Island. The views from the cottage are amazing. Being on the entrance to Dogwood Harbor provides you with a real time experience of what a waterman’s life is truly all...
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Room

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

10.0 out of 10, Exceptional, (24)
"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,
Cottage at Goose Neck Point
Living area

Cottage at Goose Neck Point

10.0 out of 10, Exceptional, (31)
"We loved everything about this sweet cottage on the water! The decor was top notch, and so welcoming! We stayed 3 nights, and can’t say enough about this beautiful area of Maryland. Great restaurants, shoppes, and delicious crabs! We also did the ferry ride over to Oxford. Had an amazing time at this property! The host also left some yummy treats, and a bottle of champagne for our anniversary! Can’t wait to come back!"
Cottage at Goose Neck Point
Pet-friendly Annapolis Home: Walk to Beach!
Property grounds

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
Amazing views, short walks to great dining!
"The cottage is lovely—vintage charm in perfect combination with the best modern updates. I was comfortable every minute I spent there..." Darcy - June 2021

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (73)
"Perfect for a romantic weekend away!"
Amazing views, short walks to great dining!
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Property grounds

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (97)
"My wife and I, and our daughter's family (including our grandkids (ages 5 and 8) spent an amazing long weekend at Spring Cove Farm. We all loved our stay so much. The house was spotlessly clean and had everything we needed and the pier/water was gorgeous with ample kayaks and paddle boards. The kids fished from the pier for hours upon hours each day, and were thrilled at the selection of toys. Our daughter and son-in-law were working remotely and the Wi-Fi and Internet worked perfectlu. Dr....
Secluded Waterfront Cottage on 200 acre farm near Queenstown
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (156)
"This was a great place to relax, have time to disconnect, and time to enjoy the company of my good friend. Loved the location and walked to the winery for a fabulous afternoon picnic. "
The Yellow Cottage on Harness Creek
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Front of Carpenter St. Cottage

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

9.8 out of 10, Exceptional, (168)
"We went to St. Michael’s for a wedding. The cottage was great. Very charming. The location was perfect. We could walk everywhere. We had great communication with the host. He was very accommodating. We will stay there again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Updated North Beach Cottage: Pet Friendly!
North Beach Vacation Rental | 3BR | 2BA | 1,440 Sq Ft | Stairs Required to Enter

Updated North Beach Cottage: Pet Friendly!

10.0 out of 10, Exceptional, (11)
"We came into town over the weekend for a family funeral. The house was perfect. So cute and clean. Location is great. House has everything you need and comfy beds. Would definitely stay here again."
Updated North Beach Cottage: Pet Friendly!
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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Other property types in Chester

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Ready to Relax and Enjoy the Water and Sunset Views?

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!

10.0 out of 10, Exceptional, (8)
"Overall it was a wonderful stay for me and 4 of my friends. Plenty of space for everyone to spread out and enjoy the wonderful view of the water while we were between wedding events. The home was off the beaten path, which added to the relaxing feeling of the house. Also it was never more than a 20 min drive to get to our events accross the island. The host was very responsive and more than accommodating for my group. The only very minor suggestion I'd like to make is that the trash in the...
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Private rear courtyard

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (20)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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.

Frequently asked questions

How much do cottages in Chester cost?
Rates for cottages in Chester range between SAR 1,686 and SAR 1,686 per night. No matter your budget, you’re sure to find the ideal place to touch base 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.
How many cottages are there in Chester?
Enjoy nature’s beauty in one of the 61 cottages waiting for you in Chester. To help you choose your ideal place, click on our handy filters to search for must-have perks or amenities.
Why book your cottage in Chester with Expedia?
We think that a vacay should be easy, so if you’re in search of cottages in Chester at a competitive rate, Expedia can help. Keep costs down and select an economical option surrounded by nature, or splurge on a luxury cottage to pamper your loved ones.
How can I find cheap cottages in Chester?
With Expedia’s useful filter tool, sourcing cheap cottages in Chester is easy. To discover accommodations that are friendly on the wallet, tailor your search results by amenities, budget and star rating.