Holiday rentals in Rock Hall

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Top-rated holiday 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.
15–22 AprIndividual Host,
£178 per night
4.94 out of 5 average rating, 127 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!
22–29 JulIndividual Host,
£212 per night
4.99 out of 5 average rating, 102 reviews
Guest favourite
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.
21–28 JunIndividual Host,
£124 per night
4.99 out of 5 average rating, 189 reviews

Popular amenities for Rock Hall holiday 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 holiday rentals in Rock Hall

Guest favourite
Houseboat in Grasonville
Cass-Away A Luxury Houseboat
30 Jan – 6 FebProfessional Host,
£163 per night
4.99 out of 5 average rating, 111 reviews
Guest favourite
Home in Rock Hall
Cozy 1920's Bungalow Near Water/Local Attractions
29 Mar – 5 Apr
£144 per night
5.0 out of 5 average rating, 63 reviews
Guest favourite
Flat in Rock Hall
Bayside bungalow cottage by the sea
16–23 Oct
£129 per night
4.96 out of 5 average rating, 47 reviews
Guest favourite
Home in Rock Hall
Chesapeake Bay Retreat w/ Views!
14–21 OctIndividual Host,
£298 per night
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Rock Hall
Inspiration Guest Suite - Cinnamon By The Bay
22–29 NovProfessional Host,
£99 per night
5.0 out of 5 average rating, 77 reviews
Guest favourite
Holiday home in Rock Hall
Quaint 3 bedroom, 1.5 bath home in Rock Hall
28 Jan – 4 FebIndividual Host,
£153 per night
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Rock Hall
Eastern Neck Water Paradise w/Brick oven & Beach
10–17 Dec
£641 per night
5.0 out of 5 average rating, 27 reviews
Guest favourite
Townhouse in Rock Hall
Walking Distance to Marinas & Main St!
25 Nov – 2 DecIndividual Host,
£187 per night
4.91 out of 5 average rating, 44 reviews
Guest favourite
Home in Rock Hall
Charming Cape By The Bay!
1–8 Jan
£222 per night
4.9 out of 5 average rating, 40 reviews
Guest favourite
Home in Rock Hall
In Town, Rock Hall, Fenced-In Yard, 1 blk to Water
29 Apr – 6 May
£188 per night
5.0 out of 5 average rating, 56 reviews
Guest favourite
Home in Rock Hall
The Blue Jimmy
23–30 Aug
£175 per night
4.95 out of 5 average rating, 19 reviews
Guest favourite
Home in Rock Hall
Rockfish Keeper
21–28 Apr
£186 per night
4.91 out of 5 average rating, 23 reviews

Quick stats about holiday 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