Rock Hall vacation rentals

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Top-rated vacation rentals in Rock Hall

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

Guest favorite
Home in Chestertown
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.
Mar 30 – Apr 6
$155 per night
4.94 out of 5 average rating, 127 reviews
Guest favorite
Cottage in Rock Hall
Cottage by the Bay in Rock Hall, MD
Sunny cottage in quiet waterside town of Rock Hall. Easy walk into downtown: grocery store, cafe, gift shop with beautiful housewares, gifts and jewelry, styling salon, quilt shop, ice cream shop, and local produce market. Gas fireplace, screened porch, stone patio, deck, several bicycles, tv for dvd's. Restaurants, crabs, Eastern Neck Wildlife Refuge, and nearby Tolchester and downtown Chestertown. Public pool, small beach (& picnic gazebos), bike around town...come to relax year round!
Jul 9 – 16
$212 per night
4.99 out of 5 average rating, 102 reviews
Guest favorite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.
Apr 5 – 12
$109 per night
4.99 out of 5 average rating, 189 reviews

Popular amenities for Rock Hall vacation rentals

Stay near Rock Hall's top sights

Waterman's Crab House33 locals recommend
Harbor Shack25 locals recommend
Bay Wolf Restaurant10 locals recommend
Bayside Foods Inc8 locals recommend
Java Rock14 locals recommend
Osprey Point Inn7 locals recommend

Other great vacation rentals in Rock Hall

Guest favorite
Camper/RV in Chestertown
Cozy Airstream on a beautiful horse farm
Jun 4 – 11
$113 per night
4.89 out of 5 average rating, 122 reviews
Guest favorite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
Aug 18 – 25
$131 per night
4.99 out of 5 average rating, 124 reviews
Guest favorite
Apartment in Chester
Cozy Waterfront Apartment Chester, MD
Feb 18 – 25
$104 per night
4.97 out of 5 average rating, 233 reviews
Guest favorite
Farm stay in Chestertown
Blue Heron Farm Waterfront Chalet
Feb 8 – 15
$266 per night
4.93 out of 5 average rating, 120 reviews
Guest favorite
Guesthouse in White Marsh
Bird River Bottega - A Waterfront Oasis!
Sep 6 – 13
$77 per night
4.97 out of 5 average rating, 137 reviews
Guest favorite
Apartment in Chestertown
Quiet escape in center of town.
Jun 16 – 23
$161 per night
4.97 out of 5 average rating, 182 reviews
Guest favorite
Guesthouse in Easton
Chill in The Crib! Easton, Maryland
Oct 22 – 27
$125 per night
4.99 out of 5 average rating, 539 reviews
Guest favorite
Cottage in Glen Burnie
Home away from home
Nov 9 – 16
$69 per night
4.93 out of 5 average rating, 133 reviews
Guest favorite
Home in Grasonville
River Front, Private Single Family Home
Sep 8 – 15
$441 per night
4.94 out of 5 average rating, 217 reviews
Guest favorite
Apartment in Pasadena
Sea Dreamer aka Phenomenal Hospitality
Oct 2 – 9
$83 per night
4.99 out of 5 average rating, 536 reviews
Guest favorite
Guesthouse in Glen Burnie
The Crab House - a Private, Waterfront Guest House
May 7 – 14
$200 per night
4.94 out of 5 average rating, 255 reviews
Guest favorite
Apartment in Crownsville
“River Sweet" Private Apartment
Mar 18 – 25
$86 per night
4.98 out of 5 average rating, 160 reviews

Other great vacation rentals in Rock Hall

Guest favorite
Vacation home in Rock Hall
Quaint 3 bedroom, 1.5 bath home in Rock Hall
Oct 21 – 28
$155 per night
5.0 out of 5 average rating, 30 reviews
Guest favorite
Apartment in Rock Hall
Inspiration Guest Suite - Cinnamon By The Bay
Jul 3 – 10
$132 per night
5.0 out of 5 average rating, 77 reviews
Guest favorite
Home in Rock Hall
Eastern Neck Water Paradise w/Brick oven & Beach
Dec 18 – 25
$709 per night
5.0 out of 5 average rating, 27 reviews
Guest favorite
Home in Rock Hall
Charming Cape By The Bay!
Nov 26 – Dec 3
$207 per night
4.9 out of 5 average rating, 40 reviews
Guest favorite
Home in Rock Hall
In Town, Rock Hall, Fenced-In Yard, 1 blk to Water
Nov 8 – 15
$179 per night
5.0 out of 5 average rating, 56 reviews
Guest favorite
Townhouse in Rock Hall
Walking Distance to Marinas & Main St!
Mar 22 – 29
$187 per night
4.91 out of 5 average rating, 44 reviews
Guest favorite
Home in Rock Hall
Rockfish Keeper
Apr 21 – 28
$174 per night
4.91 out of 5 average rating, 23 reviews
Guest favorite
Home in Rock Hall
The Blue Jimmy
Oct 23 – 30
$180 per night
4.95 out of 5 average rating, 19 reviews
Guest favorite
Home in Rock Hall
Bayside cottage steps from the harbor
Apr 18 – 25
$179 per night
4.89 out of 5 average rating, 27 reviews
Guest favorite
Home in Rock Hall
Eastern Shore Escape in the Heart of Rock Hall
Jul 24 – 31
$188 per night
4.95 out of 5 average rating, 19 reviews
Guest favorite
Home in Rock Hall
Spacious Victorian close to everything in RH!
May 5 – 12
$262 per night
4.89 out of 5 average rating, 18 reviews
Guest favorite
Home in Rock Hall
The Bay House - just a few steps to the bay!
Aug 20 – 27
$229 per night
5.0 out of 5 average rating, 27 reviews

Quick stats about vacation rentals in Rock Hall

Total rentals

40 properties

Wifi availability

30 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

1K reviews

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Rock Hall?

    Four-legged friends are welcome in Rock Hall. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Rock Hall?

    Yes! Work meets play with ease at over 10 vacation rentals in Rock Hall featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Rock Hall have a bbq area?

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

  • Do house rentals in Rock Hall have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Rock Hall. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Rock Hall?

    Rock Hall has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Rock Hall have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Rock Hall. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

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