Best Vacation Homes in Chestertown
Apartment
10.0(56 Reviews)
1 Bedroom
1 Bath
2 Guests
525 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $227/Night
7 Nights - US $1,589
Bed & Breakfast
9.6(19 Reviews)
13 Bedrooms
13 Baths
26 Guests
457.05 ft²
Breakfast- Parking
- Balcony/Terrace
View
US $359/Night
7 Nights - US $2,510
Cabin
8.0(94 Reviews)
1 Bedroom
1 Bath
- Parking
Pool- Balcony/Terrace
- View
US $137/Night
7 Nights - US $960
Apartment
10.0(31 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
Internet
US $385/Night
7 Nights - US $2,696
House
5 Bedrooms
3 Baths
10 Guests
2497.23 ft²
Hot Tub- Parking
- Balcony/Terrace
- Internet
US $701/Night
7 Nights - US $4,907
House
10.0(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
967 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $261/Night
7 Nights - US $1,828
Apartment
9.6(119 Reviews)
1 Bedroom
1 Bath
3 Guests
Private Pool- Parking
- Pool
Ocean View
US $169/Night
7 Nights - US $1,182
House
10.0(315 Reviews)
3 Bedrooms
3 Baths
8 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $564/Night
7 Nights - US $3,949
Chestertown Luxury Rentals
House
9.8(25 Reviews)
6 Bedrooms
6 Baths
14 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $1,659/Night
7 Nights - US $11,616
House
10.0(28 Reviews)
6 Bedrooms
4 Baths
13 Guests
6000 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,437/Night
7 Nights - US $10,060
House
10.0(61 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,421/Night
7 Nights - US $9,949
House
10.0(3 Reviews)
5 Bedrooms
2 Baths
7 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,337/Night
7 Nights - US $9,356
New
House
9.4(25 Reviews)
4 Bedrooms
4 Baths
14 Guests
3232 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,033/Night
7 Nights - US $7,232
House
10.0(40 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $945/Night
7 Nights - US $6,618
House
9.8(28 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $809/Night
7 Nights - US $5,665
House
4 Bedrooms
5 Baths
14 Guests
3229.17 ft²
- Parking
- Pool
- Balcony/Terrace
- Internet
US $799/Night
7 Nights - US $5,591
Chestertown Pet Friendly Vacation Rentals
Cottage
10.0(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $496/Night
7 Nights - US $3,470
House
4 Bedrooms
3 Baths
9 Guests
1959.03 ft²
- Parking
- Internet
Pet Friendly
Child Friendly
US $291/Night
7 Nights - US $2,037
Hotel
7.2(464 Reviews)
1 Bath
- Parking
- Kitchen
- Air Conditioner
- Internet
US $75/Night
7 Nights - US $524
Cabin
9.8(25 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $269/Night
7 Nights - US $1,885
House
2 Bedrooms
2 Baths
6 Guests
968.75 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
US $252/Night
7 Nights - US $1,762
House
10.0(93 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Parking
Spa- Ocean View
- Balcony/Terrace
US $591/Night
7 Nights - US $4,140
New
House
10.0(75 Reviews)
5 Bedrooms
4 Baths
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $543/Night
7 Nights - US $3,802
Apartment
10.0(104 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $209/Night
7 Nights - US $1,462
Chestertown Large Vacation Homes
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
Oceanfront- Parking
- Spa
- Ocean View
US $721/Night
7 Nights - US $5,050
House
10.0(31 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $575/Night
7 Nights - US $4,022
House
9.6(15 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $622/Night
7 Nights - US $4,351
New
House
3 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $468/Night
7 Nights - US $3,277
House
10.0(39 Reviews)
5 Bedrooms
4 Baths
15 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $933/Night
7 Nights - US $6,530
House
10.0(2 Reviews)
5 Bedrooms
2 Baths
10 Guests
2500 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $756/Night
7 Nights - US $5,292
House
5 Bedrooms
3 Baths
11 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,042/Night
7 Nights - US $7,296
House
4 Bedrooms
3 Baths
12 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $270/Night
7 Nights - US $1,892
Why Choose Rent By Owner for your Chestertown Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Chestertown
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here ensures you can fully enjoy the region's unique charm, whether you're seeking vibrant local events or a peaceful retreat in this scenic destination.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this time, you can enjoy warm weather and longer daylight hours, making it ideal for exploring the scenic surroundings and engaging in outdoor activities.
Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
Early Fall (September to October)
This period offers mild temperatures and vibrant fall foliage, providing a perfect backdrop for relaxing stays and sightseeing in the region.
Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
Off-Season Highlights
Winter (December to February)
You’ll find fewer visitors during the colder months, offering a quiet retreat with the chance to enjoy cozy stays in this destination’s charming ambiance.
Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F
Late Fall (November)
The off-peak period in late fall allows for peaceful visits as the area transitions into winter, with crisp air and fewer crowds for a more relaxed experience.
Average Temperature Daytime: 50-60°F - Nighttime: 35-45°F
Weekly Weather Forecast for Chestertown
How to Book Your Chestertown Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas perfect for meals with a view of the surrounding scenery.
- Relax in a spacious backyard or garden area to unwind after exploring the region.
- Make the most of private patios or decks for entertaining friends or family gatherings.
- Take advantage of access to scenic walking trails or nature paths nearby.
- Host barbecues or cookouts with provided outdoor grilling facilities.
- Experience waterfront views from properties situated near local waterways.
- Utilize expansive yards suitable for outdoor games and activities in this charming destination.
Top Attractions Around Chestertown
What attractions are nearby?
During your stay, you'll find a variety of activities nearby that showcase the region's natural beauty and local charm, making it an ideal destination for outdoor adventures and cultural exploration.
Family Activities
- Chestertown Maritime Museum: Dive into the region’s rich maritime history and explore exhibits that are perfect for family learning adventures.
- Washington College Campus Tours: Take a leisurely stroll through one of the area's historic campuses and enjoy its scenic beauty and educational atmosphere.
- Chew Creek Park: Spend quality time outdoors by enjoying picnicking, playground fun, or relaxing along the creek with your loved ones.
- Historic Downtown Chestertown: Experience family-friendly shopping and dining in this charming area filled with local shops and cultural attractions.
Adult Activities
- Sailing and Boating: Explore the scenic waters around the region by renting a boat or booking a sailing excursion to enjoy the tranquil Chesapeake Bay views.
- Historic District Tours: Discover the area's rich history through guided walking tours that highlight centuries-old architecture and local heritage in the heart of this charming destination.
Visit the bustling local markets for fresh produce, handcrafted goods, and regional specialties, experiencing the area's vibrant community spirit. - Art Galleries and Cultural Experiences: Immerse yourself in the regional arts scene by exploring galleries featuring local artists and attending cultural events that celebrate the area's creative heritage.
Other Places to Stay in Chestertown, MD
Great Oak Landing
Kent County
Tolchester Beach
Pomona
Fairlee
Wilmer Park
River Arts Chestertown
Garfield Center for the Arts at the Prince Theater
Historical Society of Kent County Maryland
Washington College
Rolphs Wharf Marina
Georgetown
Chestertown Travel Tips
How Can You Make the Most of Your Stay?
- Explore the local waterfront attractions: Take advantage of the area’s scenic waterways by visiting the nearby rivers and marinas, which offer relaxing boat rides and picturesque views to enhance your stay.
- Visit charming historic districts: Discover the region's rich history by strolling through its quaint streets, where unique shops and welcoming cafes provide a true taste of the local culture.
- Participate in seasonal outdoor events: Check out community festivals, outdoor markets, or outdoor concerts that showcase the vibrant spirit of this destination throughout the year.
- Plan day trips to nearby natural parks: Utilize the proximity to natural reserves and parks to enjoy hiking, birdwatching, or picnicking amid scenic landscapes that define the area.
Transportation Options
- Car Rentals: Renting a car gives you the flexibility to explore this charming region at your own pace, with local agencies conveniently located near the area.
- Public Transit: Public transportation options, including buses and shuttles, connect visitors to key points within the destination and surrounding areas for easy travel.
- Taxis and Rideshare Services: Taxis and popular rideshare services provide convenient, on-demand transportation throughout here, making short trips simple and reliable.
- Bike Rentals: For a scenic and eco-friendly way to experience the region, bike rentals are available, allowing you to enjoy the area's picturesque views up close.
Local Customs Options
- Kent County Fair: Embrace the local community spirit by participating in or observing the annual fair, a cherished tradition here that showcases regional crafts and entertainment.
- Waterfront Hospitality: Respect the region’s maritime heritage by following proper etiquette when enjoying the scenic waterways and waterfront parks.
- Folk Music Traditions: Experience the area's rich musical heritage through local folk music events that celebrate the region's cultural roots.
- Historic Preservation: Appreciate and adhere to the customs of preserving historic buildings and landmarks that reflect the area's Colonial past.
Chestertown Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Chestertown?
There are a lot of options in Chestertown. If you plan on staying in the Chestertown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chestertown:
- Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
- Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
- Circa 1900 Home in the Heart of Historic Downtown Chestertown
- Wren Retweet- Country Estate in Center of C’Town
- Eagles Point Landing-Private Pool, Dock, Pickleball
- Historic Downtown Garden Oasis with Private Patio
- Breathtaking waterfront home on the Chester River
- Harbor View Haven | Waterfront w/Hot Tub + Dock!
- Newly restored apartment in the heart of Chestertown
2. Which vacation homes in Chestertown are best for families?
If you are looking for a family-friendly vacation home in Chestertown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chestertown:
3. How many Rentbyowner vacation rentals are available in Chestertown?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 70 in the Chestertown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chestertown.
4. What is the cancellation policy for a vacation rental in this region?
Cancellation policies vary by property. You should review the specific listing details or contact the property owner directly to understand the terms and any potential fees or restrictions.
5. Are there any additional fees I should be aware of when booking here?
Additional fees such as cleaning, service charges, or security deposits may apply. These will be clearly outlined in the listing, so it’s advisable to review all details before completing your reservation.
6. How do I secure my reservation at a vacation rental in this destination?
Reservations are typically secured through a secure booking process on the listing page. For confirmation, ensure all required information is provided and communicate with the property owner if needed.
7. What amenities can I expect at a vacation rental in the area?
Amenities vary by property, but many rentals offer features like Wi-Fi, fully equipped kitchens, parking, and outdoor spaces. Check the listing details for specific amenities available at your chosen property.
8. Is there a minimum stay requirement for booking a vacation rental in this region?
Minimum stay requirements depend on the property owner’s policies and the time of year. Review each listing carefully or contact the owner to confirm the minimum stay before booking.
Chestertown Top Rated Vacation Rentals
US $119/Night
7 Nights - US $833
Hotel
8.0(248 Reviews)
1 Bath
345.64 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $206/Night
7 Nights - US $1,442
House
10.0(61 Reviews)
4 Bedrooms
4 Baths
8 Guests
4000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $1,025/Night
7 Nights - US $7,173
House
10.0(8 Reviews)
11 Bedrooms
9 Baths
30 Guests
10000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,873/Night
7 Nights - US $20,108
House
9.8(22 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $1,166/Night
7 Nights - US $8,162
