Vacation rentals in Rock Hall

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Top-rated vacation rentals in Rock Hall

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

Guest favourite
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.
Jun. 16 – 23
$303 CAD per night
4.94 out of 5 average rating, 127 reviews
Guest favourite
Apartment in Rock Hall
Inspiration Guest Suite - Cinnamon By The Bay
Inspiration is a cozy, bright studio with a full-size bed, seating area, kitchenette, and workspace. It is located upstairs in Cinnamon By The Bay's in-town suites. Main Street shopping, Java Rock coffee shop, and The Mainstay music venue are right outside the front entrance. Ferry Beach, Eastern Neck Wildlife Refuge, museums, charter fishing, kayaking, and marinas are a short walk or drive. Enjoy stunning sunsets and lively conversations on the community deck. Suite is limited to 2 guests.
Aug. 23 – 30
$229 CAD per night
5.0 out of 5 average rating, 77 reviews
Guest favourite
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!
Oct. 9 – 16
$336 CAD per night
4.99 out of 5 average rating, 102 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 favourite
Home in Rock Hall
In Town, Rock Hall, Fenced-In Yard, 1 blk to Water
Jul. 24 – 31
$320 CAD per night
5.0 out of 5 average rating, 57 reviews
Guest favourite
Home in Rock Hall
Charming Cape By The Bay!
Oct. 11 – 18
$340 CAD per night
4.9 out of 5 average rating, 40 reviews
Guest favourite
Home in Rock Hall
The Blue Jimmy
May 16 – 23
$299 CAD per night
4.95 out of 5 average rating, 19 reviews
Guest favourite
Home in Rock Hall
Rockfish Keeper
Jul. 22 – 29
$390 CAD per night
4.91 out of 5 average rating, 23 reviews
Guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
Dec. 4 – 11
$200 CAD per night
4.93 out of 5 average rating, 99 reviews
Guest favourite
Home in Rock Hall
Bayside cottage steps from the harbor
Apr. 18 – 25
$288 CAD per night
4.89 out of 5 average rating, 27 reviews
Guest favourite
Home in Rock Hall
Eastern Neck Water Paradise w/Brick oven & Beach
Jan. 8 – 15
$1,212 CAD per night
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Rock Hall
The Bay House - just a few steps to the bay!
Sep. 24 – Oct. 1
$401 CAD per night
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Rock Hall
Waterfront w/upper sundeck and kayaks/paddleboad
Nov. 17 – 24
$857 CAD per night
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Rock Hall
Eastern Shore Escape in the Heart of Rock Hall
Jun. 6 – 13
$340 CAD per night
4.95 out of 5 average rating, 19 reviews
Guest favourite
Apartment in Chestertown
Waterfront historic district 1BR Apartment
Nov. 13 – 20
$229 CAD per night
5.0 out of 5 average rating, 63 reviews
Guest favourite
Home in Rock Hall
Spacious Victorian close to everything in RH!
Jun. 7 – 14
$466 CAD per night
4.89 out of 5 average rating, 18 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

Destinations to explore

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