House holiday rentals in Rock Hall

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Top-rated house rentals in Rock Hall

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Guest favourite

Home in Chestertown

4.94 out of 5 average rating, 129 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

$372 NZD per night

Guest favourite

Home in Shady Side

5.0 out of 5 average rating, 118 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!

18–25 Jan

$849 NZD per night

Guest favourite

Home in Rock Hall

5.0 out of 5 average rating, 63 reviews

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

9–16 Dec

$394 NZD per night

Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 155 reviews

Nicely refurbished historic house near town center

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.

18–25 Jan

$612 NZD per night

Guest favourite

Home in Grasonville

4.94 out of 5 average rating, 226 reviews

River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

17–24 Nov

$800 NZD per night

Guest favourite

Home in Glen Burnie

4.97 out of 5 average rating, 398 reviews

Secluded acre near BWI and Baltimore

Secluded suburban acre 8 minutes from BWI Airport, 15 minutes from Baltimore's Inner Harbor and from Fort Meade, and 45 minutes from Washington DC. Private house attached to host house has 1220 square feet of cozy comfort--4 times the size of a hotel room! House includes 2 bedrooms (one queen, one double), 1.5 baths, living room, foyer, dining room, full kitchen, and washer/dryer. The one-acre lot has hundreds of trees and is great for pets. Level 2 charging station is good for all EVs.

25 Jun – 2 Jul

$282 NZD per night

Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 104 reviews

Waterfront w/Pier &Walking Distance to Chestertown

This 4 bedroom, 3 bath waterfront home is a terrific place to enjoy time with family and friends. This home has amazing amenities; from the stylish updated renovations and furnishings (some antiques), the screened porch, patio, fire pit, hot tub (Oct - April), sporting equipment, to the spacious, comfortable, indoor & outdoor gathering spaces. The kitchen is well-appointed with gourmet appliances, and plenty of hosting and culinary supplies to savor wonderful meals together at the house.

3–10 Jan

$999 NZD per night

Guest favourite

Home in Annapolis

4.89 out of 5 average rating, 182 reviews

Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

27 Sep – 4 Oct

$350 NZD per night

Guest favourite

Home in Annapolis

4.99 out of 5 average rating, 199 reviews

Cape St Claire waterfront getaway

This is a private over the garage apartment located in Cape St Claire, about 5 miles from downtown Annapolis, 2 miles to the Bay Bridge. Private entrance, on site parking, 1- 2 guests. We encourage our guests to enjoy the large back yard patio with magnificent views of the Magothy River and Chesapeake Bay ! Approximately 30 miles to Washington, and Baltimore. 30 minutes to BWI airport. TV and internet. A community beaches just a short walk away. ADULTS ONLY, NO SMOKING, NO PETS.

1–8 Aug

$268 NZD per night

Guest favourite

Home in Rock Hall

5.0 out of 5 average rating, 18 reviews

Chesapeake Bay Retreat w/ Views!

Step into a relaxing retreat at this picturesque vacation rental on Chesapeake Bay! Complete with 2 bedrooms and 2 bathrooms, this spacious home offers a cozy fireplace and a stunning deck overlooking the water — perfect for enjoying the sunset! Explore the nearby Eastern Neck National Wildlife Refuge or take a scenic drive to the quaint shops and seafood restaurants in town. Whether you're seeking outdoor adventures or a peaceful coastal getaway, you’ll love this Rock Hall property!

3–10 Oct

$715 NZD per night

Guest favourite

Home in Rock Hall

5.0 out of 5 average rating, 66 reviews

Cozy 1920's Bungalow Near Water/Local Attractions

Updated 1920's bungalow near all Rock Hall has to offer. Blocks away from the Bay, marinas and center of town. Coffee shop, grocery and other shops 2 blocks away. Walk to several restaurants. Cozy and very comfortable. Quiet street, and peaceful at night. This house is an ideal Rock Hall location. This home is well stocked, so most condiments, coffee, tea, sodas and water are included. There are also many toiletry and first aid products. No need to bring soap or shampoo.

20–27 Aug

$451 NZD per night

Guest favourite

Home in Chestertown

4.94 out of 5 average rating, 102 reviews

Classic Victorian in Chestertown

A delightful hideaway all to yourself! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet kitchen, two porches, antiques, rugs, and several writing spaces. Dual zone HVAC, washer & dryer, high-speed internet. Plenty of on-street parking. Professional cleaning before every visit (alcohol and/or bleach solution), combined with complete ventilation of the house 24 hours ahead of arrival.

20–27 Sep

$382 NZD per night