Holiday houses in Rock Hall

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Top-rated holiday rentals in Rock Hall

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Guest favourite

Home in Chestertown

4.94 out of 5 average rating, 128 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.

4–11 May

$378 NZD per night

Guest favourite

Apartment in Pasadena

4.99 out of 5 average rating, 547 reviews

Sea Dreamer aka Phenomenal Hospitality

Stunning sunrises free in a tranquil, riverfront, apartment with front entrance. Split foyer home, I am upstairs, you are downstairs. 2 separate bedrooms, one overlooking the river. Living room includes dining area, office space, comfy seating, and a massage chair!. Full bath, best showerhead, soaps, shampoos, and towels. Pull out sofa bed for larger parties. Kitchenette has everything necessary to cook with. BWI 20 min, 40 Annapolis, 60 to DC. Patio, fire pit, grill, deck and beach walks.

14–21 Nov

$179 NZD per night

Guest favourite

Guest suite in Arnold

4.96 out of 5 average rating, 565 reviews

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

14–21 Jul

$212 NZD per night

Guest favourite

Cottage in Rock Hall

4.99 out of 5 average rating, 102 reviews

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 Oct

$419 NZD per night

Guest favourite

Guest suite in Chestertown

4.99 out of 5 average rating, 130 reviews

Chestertown - Eastern Shore Getaway

"A little slice of Americana" (commented one of our guests) This century-old three-story home is in the beautiful historic district of Chestertown, which sits on the majestic, unspoiled Chester River, on Maryland's famous Eastern Shore. We are right across the street from Washington College and just blocks from the quaint ambiance of High Street. The commercial district is equally accessible, with banks, grocery and liquor stores, restaurants, and more, a few blocks up Washington Avenue.

11–18 Jul

$346 NZD per night

Guest favourite

Casa particular in Chestertown

4.93 out of 5 average rating, 102 reviews

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

10–17 Feb

$249 NZD per night

Guest favourite

Guesthouse in White Marsh

4.97 out of 5 average rating, 140 reviews

Bird River Bottega - A Waterfront Oasis!

Private entrance studio located on a waterfront property. The Bottega is perfect for couples, solo travelers, and business professionals; best suited for two travelers. Enjoy your morning coffee by the water and watch the Ospreys, herons, ducks, hawks, and bald eagles galore. Whether you are fishing, lounging, or kayaking the Bird River (home to the Chesapeake Bay), you are bound for relaxation. Surrounded by a plethora of eateries, shopping, and entertainment all within a 25 minute drive.

7–14 Oct

$186 NZD per night

Guest favourite

Guesthouse in Annapolis

4.9 out of 5 average rating, 206 reviews

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

10–17 Jan

$204 NZD per night

Guest favourite

Guest suite in Chestertown

4.99 out of 5 average rating, 191 reviews

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.

1–8 Oct

$263 NZD per night

Guest favourite

Apartment in Crownsville

4.98 out of 5 average rating, 163 reviews

“River Sweet" Private Apartment

River Sweet has everything you need for a fun and relaxing getaway. Cozy and clean, River Sweet provides all the comforts of home, including your own driveway and entrance. You'll delight in privacy while enjoying a safe, waterfront neighborhood. A local mini mart and restaurant are close by. And, you are centrally located between Annapolis, Baltimore and Washington for fun excursions! Please let us know if you need a long-term stay. We would be happy to accommodate you.

16–23 Aug

$213 NZD per night

Guest favourite

Cottage in Rock Hall

4.95 out of 5 average rating, 133 reviews

The Blissful Retreat @theblissfulretreat

Serene space nestled in the woods; with water views. You have your own private cottage on our 10 acre property to watch the sunsets and enjoy the nature all around. You'll spot deer, bunnies, frogs, turtles, birds and so much more from the lovely front porch! As a Nurse I can guarantee our space has always been cleaned and sanitized to the highest standards. Check us out on insta for more blissfulness - theblissfulretreat and FB- theblissfulretreatrockhall

14–21 Dec

$507 NZD per night

Guest favourite

Campervan/RV in Chestertown

4.89 out of 5 average rating, 123 reviews

Cozy Airstream on a beautiful horse farm

You'll love this cozy 32' 1989 Airstream Excella 1000. It's got a comfy queen size bed in the bedroom and a couch that converts to a full size bed that could sleep another adult comfortably or a couple of kids. The farm is beautiful - you'll feel like you're on vacation. We have a fire pit out front and an 8' galvanized shallow trough pool in the summer. Complete with stove, fridge, microwave, gas grill and Keurig.

5–12 Aug

$246 NZD per night