Vacation rentals in Chestertown

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Top-rated vacation rentals in Chestertown

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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

R3,767 ZAR per night

Guest favorite

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!

Jul 14 – 21

R2,149 ZAR 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 17 – 24

R4,012 ZAR per night

Guest favorite

Cabin in Chestertown

4.98 out of 5 average rating, 215 reviews

Rivershore Retreat

Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

Dec 4 – 11

R5,917 ZAR 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.

Jul 11 – 18

R3,676 ZAR 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!

Feb 10 – 17

R2,616 ZAR 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.

Oct 7 – 14

R1,700 ZAR 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.

Jan 10 – 17

R1,878 ZAR per night

Guest favorite

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.

Feb 9 – 16

R10,546 ZAR 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

R2,677 ZAR per night

Guest favorite

Guesthouse in Easton

4.99 out of 5 average rating, 545 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for two individuals (No children under 8 years of age.), and please limit your visit to one vehicle only.

Jan 25 – 30

R2,756 ZAR 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.

Aug 5 – 12

R2,495 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chestertown vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Chestertown's top sights

Fish Whistle23 locals recommend

Luisa's Cucina Italiana27 locals recommend

Procolino's Pizza15 locals recommend

ACME Markets13 locals recommend

98 Cannon Riverfront Grille9 locals recommend

Uncle Charlie's Bistro14 locals recommend

Other great vacation rentals in Chestertown

Guest favorite

Apartment in Pasadena

4.99 out of 5 average rating, 547 reviews

Sea Dreamer aka Phenomenal Hospitality

Nov 14 – 21

R1,810 ZAR per night

Guest favorite

Home in Chestertown

4.92 out of 5 average rating, 166 reviews

Historic Chestertown

Jan 19 – 26

R6,444 ZAR per night

Guest favorite

Guesthouse in Grasonville

4.9 out of 5 average rating, 203 reviews

Eastern Shore Charm on Winchester Creek

Oct 2 – 9

R2,526 ZAR per night

Guest favorite

Apartment in Chesapeake City

4.93 out of 5 average rating, 142 reviews

Bohemia Vista CC Horse Farm Apartment

May 3 – 10

R2,494 ZAR per night

Guest favorite

Home in Annapolis

4.96 out of 5 average rating, 109 reviews

Historic Downtown in-law suite

Apr 15 – 22

R2,330 ZAR per night

Guest favorite

Apartment in Crownsville

4.98 out of 5 average rating, 163 reviews

“River Sweet" Private Apartment

Aug 16 – 23

R2,050 ZAR per night

Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 68 reviews

Waterfront historic district 1BR Apartment

Jan 24 – 31

R3,077 ZAR per night

Guest favorite

Apartment in Chestertown

4.92 out of 5 average rating, 97 reviews

Downtown Studio Apartment

Feb 23 – Mar 2

R2,641 ZAR per night

Show all

Other great vacation rentals in Chestertown

Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 46 reviews

Bright, new apartment in the heart of Chestertown

Nov 12 – 19

R4,659 ZAR per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 13 reviews

NEW Chestertown Retreat

Apr 12 – 19

R4,032 ZAR per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 24 reviews

125 High - Luxury Historical Brick Victorian

Apr 8 – 15

R6,606 ZAR per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 75 reviews

River front cottage with private dock & water fun

Nov 15 – 22

R9,916 ZAR per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 37 reviews

Waterfront house with private dock & kayaks!

Jul 11 – 18

R4,929 ZAR per night

Guest favorite

Home in Chestertown

4.93 out of 5 average rating, 30 reviews

Harbor View Haven | Waterfront w/ HOT TUB + Dock!

Dec 5 – 12

R9,350 ZAR per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 51 reviews

Lovely, Recently-Renovated Home in Chestertown

Nov 20 – 27

R3,902 ZAR per night

Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 20 reviews

In Town Chestertown Rancher (1 Block to College)

Sep 5 – 12

R4,348 ZAR per night

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Quick stats about vacation rentals in Chestertown

Total rentals
40 properties
Wifi availability
40 properties include access to wifi
Rentals with dedicated workspaces
20 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
2.5K reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Chestertown?
Yes! Work meets play with ease at over 20 vacation rentals in Chestertown featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Chestertown?
Four-legged friends are welcome in Chestertown. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Chestertown have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Chestertown. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chestertown have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Chestertown. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chestertown have wifi?
Absolutely! We offer over 20 house rentals with wifi in Chestertown. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Chestertown?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a bbq area, over 20 homes with wifi, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Chestertown

Top-rated vacation rentals in Chestertown

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Chestertown vacation rentals

Stay near Chestertown's top sights

Other great vacation rentals in Chestertown

Apartment in Pasadena

Home in Chestertown

Guesthouse in Grasonville

Apartment in Chesapeake City

Home in Annapolis

Apartment in Crownsville

Apartment in Chestertown

Apartment in Chestertown

Other great vacation rentals in Chestertown

Apartment in Chestertown

Home in Chestertown

Home in Chestertown

Home in Chestertown

Home in Chestertown

Home in Chestertown

Home in Chestertown

Home in Chestertown

Quick stats about vacation rentals in Chestertown

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Chestertown?

Are there pet-friendly vacation rentals in Chestertown?

Do house rentals in Chestertown have a bbq area?

Do house rentals in Chestertown have self check-in?

Do house rentals in Chestertown have wifi?

What are the most popular amenities for House Rentals in Chestertown?

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