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.

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Guest favorite

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.

May 4 – 11

G$41,009 GYD per night

Guest favorite

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.

Feb 22 – Mar 1

G$19,702 GYD per night

Guest favorite

Guest suite in Arnold

4.96 out of 5 average rating, 563 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!

Jul 8 – 15

G$23,390 GYD per night

Guest favorite

Apartment in Chestertown

4.97 out of 5 average rating, 193 reviews

Quiet, pet frienly, escape in center of town

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in every window. Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, and Keurig/coffee makers. Comfortable king bed with luxury linens, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

Dec 15 – 22

G$43,583 GYD per night

Guest favorite

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!

Jul 29 – Aug 5

G$50,853 GYD per night

Guest favorite

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.

Sep 12 – 19

G$28,067 GYD per night

Guest favorite

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!

Jan 18 – 25

G$28,448 GYD per night

Guest favorite

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.

Dec 25 – Jan 1

G$20,446 GYD per night

Guest favorite

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.

Dec 15 – 22

G$18,818 GYD per night

Guest favorite

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.

Oct 1 – 8

G$29,265 GYD per night

Guest favorite

Cottage in Rock Hall

4.95 out of 5 average rating, 132 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

Feb 17 – 24

G$57,289 GYD per night

Guest favorite

Camper/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.

Jul 23 – 30

G$27,156 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Rock Hall vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

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

Guesthouse in Easton

4.99 out of 5 average rating, 543 reviews

Chill in The Crib! Easton, Maryland

Nov 10 – 15

G$30,004 GYD per night

Guest favorite

Apartment in Rock Hall

4.96 out of 5 average rating, 47 reviews

Bayside bungalow cottage by the sea

Jul 13 – 20

G$29,518 GYD per night

Guest favorite

Apartment in Rock Hall

5.0 out of 5 average rating, 15 reviews

Traveler Guest Suite - Cinnamon By The Bay

Dec 4 – 11

G$22,990 GYD per night

Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 16 reviews

Chesapeake Bay Retreat w/ Views!

Nov 21 – 28

G$59,707 GYD per night

Guest favorite

Vacation home in Rock Hall

5.0 out of 5 average rating, 35 reviews

Quaint 3 bedroom, 1.5 bath home in Rock Hall

Mar 17 – 24

G$37,129 GYD per night

Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 65 reviews

Cozy 1920's Bungalow Near Water/Local Attractions

Mar 12 – 19

G$42,237 GYD per night

Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 62 reviews

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

Oct 19 – 26

G$43,221 GYD per night

Guest favorite

Townhouse in Rock Hall

4.91 out of 5 average rating, 45 reviews

Walking Distance to Marinas & Main St!

Jul 26 – Aug 2

G$46,670 GYD per night

Show all

Other great vacation rentals in Rock Hall

Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 27 reviews

The Bay House - just a few steps to the bay!

Dec 23 – 30

G$55,014 GYD per night

Guest favorite

Home in Rock Hall

4.89 out of 5 average rating, 28 reviews

Bayside cottage steps from the harbor

Jul 23 – 30

G$58,495 GYD per night

Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 28 reviews

Eastern Neck Water Paradise w/Brick oven & Beach

May 4 – 11

G$170,344 GYD per night

Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 67 reviews

Waterfront historic district 1BR Apartment

Jul 22 – 29

G$34,419 GYD per night

Guest favorite

Home in Rock Hall

4.91 out of 5 average rating, 23 reviews

Rockfish Keeper

Sep 24 – Oct 1

G$48,998 GYD per night

Guest favorite

Home in Rock Hall

4.89 out of 5 average rating, 18 reviews

Spacious Victorian close to everything in RH!

Dec 25 – Jan 1

G$63,125 GYD per night

Guest favorite

Bungalow in Rock Hall

4.94 out of 5 average rating, 32 reviews

Welcome to Mermaid Haven!

Feb 27 – Mar 6

G$66,694 GYD per night

Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 8 reviews

Waterfront w/upper sundeck and kayaks/paddleboad

Feb 9 – 16

G$239,617 GYD per night

Show all

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
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
920 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 10 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.

Rock Hall vacation rentals

Top-rated vacation rentals in Rock Hall

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Rock Hall vacation rentals

Stay near Rock Hall's top sights

Other great vacation rentals in Rock Hall

Guesthouse in Easton

Apartment in Rock Hall

Apartment in Rock Hall

Home in Rock Hall

Vacation home in Rock Hall

Home in Rock Hall

Home in Rock Hall

Townhouse in Rock Hall

Other great vacation rentals in Rock Hall

Home in Rock Hall

Home in Rock Hall

Home in Rock Hall

Apartment in Chestertown

Home in Rock Hall

Home in Rock Hall

Bungalow in Rock Hall

Home in Rock Hall

Quick stats about vacation rentals in Rock Hall

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there pet-friendly vacation rentals in Rock Hall?

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

Do house rentals in Rock Hall have a bbq area?

Do house rentals in Rock Hall have air conditioning?

Are there family-friendly house rentals in Rock Hall?

Do house rentals in Rock Hall have wifi?

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