Compare Chester Cottage Rentals

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Featured Chester Cottages

The Heron's Nest at Atlantic Marina

The Heron's Nest at Atlantic Marina

Guests staying at this cottage can enjoy an outdoor pool, barbecue grills, and a garden.
Pool
Kitchen
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

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

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Secluded Waterfront Cottage on 200 acre farm near Queenstown

Secluded Waterfront Cottage on 200 acre farm near Queenstown

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

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

At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
Peaceful getaway convenient to local amenities including beach, boating & food

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

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Kitchen
Washer
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats

$583 nightly
The price is $665 total per night
$665 total
Oct 13 - Oct 14
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
The Middle Point Cabin in Saint Michaels

The Middle Point Cabin in Saint Michaels

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

At this cottage, guests have access to a gym, laundry facilities, and barbecue grills. This beach cottage also has a garden.
Kitchen
Washer
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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.

Hotel Options in Chester

    Historic Inns of Annapolis

    Historic Inns of Annapolis

    58 State Circle, Annapolis, MD
    $145 nightly
    The price is $166 total per night from Nov 3 to Nov 4
    $166 total
    Nov 3 - Nov 4
    Total with taxes and fees
    8.8/10 Excellent! (1,833 reviews)
    Graduate by Hilton Annapolis

    Graduate by Hilton Annapolis

    126 West St, Annapolis, MD
    $183 nightly
    The price is $209 total per night from Oct 30 to Oct 31
    $209 total
    Oct 30 - Oct 31
    Total with taxes and fees
    9.2/10 Wonderful! (1,002 reviews)
    Sonesta ES Suites Annapolis

    Sonesta ES Suites Annapolis

    170 Admiral Cochrane Dr, Edgewater, MD
    $92 nightly
    The price is $105 total per night from Oct 29 to Oct 30
    $105 total
    Oct 29 - Oct 30
    Total with taxes and fees
    8.8/10 Excellent! (906 reviews)

Cottages

Book a cottage in Chester
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Chester. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Chester better.

Cottage apartments in Chester range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Chester
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Chester and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Chester cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Chester. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Chester Cottages essential information

Accommodation
84 Cottages
Lowest Price
$105
Highest Price
$665
Popular accommodation
The Heron's Nest at Atlantic Marina, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, Secluded Waterfront Cottage on 200 acre farm near Queenstown, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Peaceful getaway convenient to local amenities including beach, boating & food, Chesapeake Cottages- 2 Quaint Waterfront Retreats, The Middle Point Cabin in Saint Michaels, Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK