Vacation rentals in Chestertown

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Top-rated vacation rentals in Chestertown

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Home in Chestertown

4.94 out of 5 average rating, 127 reviews

CHESAPEAKE SUNSETS

Escape to a quaint bayside cottage with sweeping views of the Chesapeake. Relax and enjoy beautiful sunsets from the bayside sundeck, screened porch or from the comfort of your home. Less than 2 miles to the seasonal Shanty Bar at Tolchester Marina featuring live music, dining and its own beach. One mile from a private community boat ramp to launch your water toys. 800 sq ft 2 bedroom 1 bath house is on Maryland’s Eastern Shore less than 2 hours from Washington, Baltimore and Philadelphia.

Aug 6 – 13

$170 per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 151 reviews

Historic house, near town center, pet friendly

Renovated 19th century home with all modern conveniences. First floor bedroom with private bath. Hi speed internet. Pets welcome! Located in the historic district of Chestertown, a 3 block walk from both Washington College and the C'town waterfront. 2 primary bedroom suites (one on the second floor has a king bed) 2 more bedrooms with queen beds. 1 loft which is connected to the a 2nd story bedroom has 2 twins. Fenced yard and over an acre of totally private gardens. Fire pit.

Dec 10 – 17

$307 per night
Guest favorite

Cabin in Chestertown

4.98 out of 5 average rating, 215 reviews

Rivershore Retreat

Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

Apr 4 – 11

$268 per night

Popular amenities for Chestertown vacation rentals

Stay near Chestertown's top sights

Fish Whistle23 locals recommend
Luisa's Cucina Italiana27 locals recommend
Procolino's Pizza15 locals recommend
ACME Markets13 locals recommend
98 Cannon Riverfront Grille9 locals recommend
Uncle Charlie's Bistro15 locals recommend

Other great vacation rentals in Chestertown

Guest favorite

Apartment in Pasadena

4.99 out of 5 average rating, 542 reviews

Sea Dreamer aka Phenomenal Hospitality

Nov 16 – 23

$83 per night
Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 202 reviews

Calico Cottage Guest House, king bed, free parking

Nov 14 – 21

$85 per night
Guest favorite

Home in Grasonville

4.94 out of 5 average rating, 221 reviews

River Front, Private Single Family Home

Dec 22 – 29

$466 per night
Guest favorite

Home in Annapolis

4.96 out of 5 average rating, 103 reviews

Historic Downtown in-law suite

Jan 9 – 16

$106 per night
Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 64 reviews

Waterfront historic district 1BR Apartment

Feb 3 – 10

$141 per night
Guest favorite

Apartment in Chestertown

4.92 out of 5 average rating, 95 reviews

Downtown Studio Apartment

Jan 4 – 11

$120 per night
Guest favorite

Guest suite in Chestertown

4.93 out of 5 average rating, 45 reviews

Historic Downtown Garden Oasis with Private Patio

Sep 10 – 17

$144 per night
Guest favorite

Casa particular in Chestertown

4.93 out of 5 average rating, 99 reviews

Red, White & Waterview Studio Apt with pool

Nov 26 – Dec 3

$119 per night
Guest favorite

Home in Chestertown

4.96 out of 5 average rating, 69 reviews

Cozy 3-bedroom home w/ screened in porch & firepit

Jan 14 – 21

$172 per night
Guest favorite

Home in Chestertown

4.98 out of 5 average rating, 40 reviews

2 Beds, 2.5 Baths, Perfect Downtown Location

May 8 – 15

$160 per night
Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 44 reviews

Bright, new apartment in the heart of Chestertown

Dec 2 – 9

$191 per night
Guest favorite

Home in Chestertown

4.88 out of 5 average rating, 25 reviews

Beautifully remodeled home in Historic Chestertown

Jun 27 – Jul 4

$155 per night

Other great vacation rentals in Chestertown

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 14 reviews

Down by the River

Oct 13 – 20

$700 per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 50 reviews

Lovely, Recently-Renovated Home in Chestertown

Oct 22 – 29

$150 per night
Guest favorite

Apartment in Chestertown

4.92 out of 5 average rating, 62 reviews

1-br apt in downtown Chestertown

Apr 10 – 17

$141 per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 23 reviews

Magnolia House ~Historic Downtown w/Private Garden

Oct 24 – 31

$522 per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 19 reviews

In Town Chestertown Rancher (1 Block to College)

Jun 4 – 11

$196 per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 16 reviews

Goose Haven, new waterfront house on Fairlee Creek

Jun 21 – 28

$482 per night
Guest favorite

Apartment in Chestertown

4.98 out of 5 average rating, 87 reviews

RIVER WATCH

Aug 16 – 23

$237 per night
Guest favorite

Apartment in Rock Hall

4.96 out of 5 average rating, 47 reviews

Bayside bungalow cottage by the sea

Aug 20 – 27

$125 per night
Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 11 reviews

Chesapeake Bay Retreat w/ Views!

Aug 13 – 20

$238 per night
Superhost

Cottage in Betterton

4.8 out of 5 average rating, 51 reviews

Cottage By the Chesapeake

May 13 – 20

$107 per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 23 reviews

Private Cottage, Chestertown - "Cliff Pines"

Jul 23 – 30

$225 per night
Guest favorite

Home in Greensboro

4.95 out of 5 average rating, 44 reviews

Cozy 2 bedroom home on wooded private lane

Feb 5 – 12

$113 per night

Quick stats about vacation rentals in Chestertown

Total rentals

50 properties

Wifi availability

50 properties include access to wifi

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

2.4K reviews

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Chestertown?

    Yes! Work meets play with ease at over 20 vacation rentals in Chestertown featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Chestertown?

    Four-legged friends are welcome in Chestertown. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Chestertown have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Chestertown. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chestertown have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in in Chestertown. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chestertown have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Chestertown. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Chestertown?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 10 homes with self check-in, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Kent County
  5. Chestertown