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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare 420 Vacation Homes in Chestertown with updated reviews, rates, and availability.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Terrace/patio

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
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, (206)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Freshly renovated 3-story home 1 block from USNA!

Freshly renovated 3-story home 1 block from USNA!

10.0 out of 10, Exceptional, (29)
"Best property we’ve stayed at in Annapolis by far. We look forward to our next stay. The property was spacious, well stocked, cozy and full of beautiful light! Central location to everything you need. Friendly neighborhood and great location. "
The price is SAR 555
SAR 2,411 total
includes taxes & fees
17 Feb - 18 Feb
Freshly renovated 3-story home 1 block from USNA!
Pet-Friendly Home on Chester River w/ Dock!
Chestertown Vacation Rental | 4BR | 4.5BA | 6 Steps Required | 3,232 Sq Ft

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (4)
"An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!"
Pet-Friendly Home on Chester River w/ Dock!
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Annapolis Vacation Rental | 4BR | 3.5BA | 2,900 Sq Ft | Stairs Required

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Walk to Lake & Boat Ramp: Central Gem in Annapolis
Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning
Living area

Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning

3.0 star property
Historic Rowe House 2br 2.5ba Cityscape View 2 Bedroom Home by RedAwning
Charming Historic Townhouse Steps From USNA
Interior

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (21)
"I love this property and host! Incredible place to stay close to museums the Naval Academy, local shopping, excellent restaurants and the airport. I will highly recommend this property to friends & family. "
Charming Historic Townhouse Steps From USNA
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Living/Kitchen

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (16)
"One of if not the best VRBO I have ever stayed in. Incredible property and host"
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Netflix, Hulu, Disney+ Available

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

10.0 out of 10, Exceptional, (13)
"This property from website fit the beds and bathrooms we needed so everyone got their own bed. When we opened the front door it was better looking in person than on web.Would absolutely recommend this place and we will definitely be back."
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Baseball Lovers Paradise!
Bathroom

Baseball Lovers Paradise!

9.4 out of 10, Exceptional, (6)
"Difficult getting in touch with and not timely responses with host. The house was clean….but the bedspreads and throw pillows need washing. They smell and are very dirty. There were no wash clothes to shower with. The house was not dirty itself. Bathrooms, bedrooms, and kitchen were clean. The location was great for our needs and very close to Ripken. Directions and address to the location need to be better communicated. Overall, I would stay there again and we do travel there a lot. I would...
Baseball Lovers Paradise!
Cozy 5 bedroom house with attached guest suite
Exterior

Cozy 5 bedroom house with attached guest suite

Cozy 5 bedroom house with attached guest suite
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront with private pier and great views

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Circa 1700 Chesapeake Colonial home on the National Register.
Pool

Circa 1700 Chesapeake Colonial home on the National Register.

9.8 out of 10, Exceptional, (50)
"Very cool house with great host. Very spacious. Excellent kitchen and very cozy. It would have been helpful to know about the staircases. We had an 8 month pregnant woman and 2 year old that were not able to come but it would have been an issue as getting to the single bed rooms is challenging."
Circa 1700 Chesapeake Colonial home on the National Register.
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Living area

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

10.0 out of 10, Exceptional, (21)
"Convenient to restaurants and a warm, comfortable place to gather and relax after a hard, cold waterfowl hunt"
The price is SAR 295
SAR 953 total
includes taxes & fees
19 Feb - 20 Feb
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
Pool

Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

8.8 out of 10, Excellent, (11)
"The location is spectacular with expansive views of the Chesapeake Bay and the Bay Bridge. The house itself is immaculate and had lots of space for our family. I would imagine it's even better in the summer when the pool is available.One caution: the playhouse is really cool but not a place to let younger kids play unsupervised."
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
Luxury 3 bed row home in the heart of downtown Fells Point

Luxury 3 bed row home in the heart of downtown Fells Point

10.0 out of 10, Exceptional, (14)
"The house is nice and clean. Close to shops and restaurants. We will stay here again."
Luxury 3 bed row home in the heart of downtown Fells Point
BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (33)
"The bay cottage's porch was a perfect spot to enjoy a bottle of wine and snacks provided by the thoughtful hosts. Clever decor , furnishings, and sauna made our stay special and warm. Had crab dinner viewing sunset over the bay at dockside suggested by hosts. we hope to return. "
The price is SAR 656
SAR 994 total
includes taxes & fees
16 Feb - 17 Feb
BAYSIDE BUNGALOW
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Exterior

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!

10.0 out of 10, Exceptional, (18)
"Good location."
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Home w/ Patio & Large Yard in Parkville
Parkville Vacation Rental | 4BR | 2BA | 2,400 Sq Ft | Stairs Required

Home w/ Patio & Large Yard in Parkville

Home w/ Patio & Large Yard in Parkville
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 Chestertown

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Terrace/patio

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
'At Fells Point' CitySide - 'Tons better than a hotel!'
CitySide Living Room & Sofa Bed

'At Fells Point' CitySide - 'Tons better than a hotel!'

9.8 out of 10, Exceptional, (185)
"The property is compact but cute. They have a door that slides across doorway between the bedroom and the living room that blocks noise from the outside. We did find the property chilly but when we contacted the owner, he had one of his staff come over, wait a few minutes for us outside, and provide us with space heaters that warmed the place up very effectively and quietly. We felt valued and cared for. I highly recommend this cozy little place and the people who manage it!"
The price is SAR 330
SAR 771 total
includes taxes & fees
18 Feb - 19 Feb
'At Fells Point' CitySide - 'Tons better than a hotel!'
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
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.