Chestertown, MD Apartments For Rent
1,776 rentals
Use arrow keys to navigateNEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLY
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLYTotal price$2,024 - $3,267/mo
1-3 Beds
1-2 BathsMarlowe Gateway | 2790 Grand Ave,
Saint Petersburg, FL 33716
Use arrow keys to navigatePET FRIENDLY$2,203 - $4,668/mo1-3 Beds1-2 BathsMarina Club Apartment homes | 4341 34th St S,
Saint Petersburg, FL 33711
Use arrow keys to navigatePET FRIENDLYTotal price$1,719 - $3,613/moStudio-3 Beds1-2 BathsiMMix | 3201 34th St S,
Saint Petersburg, FL 33711
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLY$1,950 - $3,680/moStudio-2 Beds1-2 Baths1701 Central Apartments | 1701 Central Ave,
Saint Petersburg, FL 33713
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLY
Use arrow keys to navigateSPECIAL OFFERPET FRIENDLY$2,550 - $4,370/mo1-3 Beds1-2 BathsModera St. Petersburg | 201 17th St S,
Saint Petersburg, FL 33712
SPECIAL OFFERPET FRIENDLY$1,590 - $2,935/mo1-3 Beds1-2 BathsThe Courtney at Bay Pines | 4652 Miramar Dr,
Saint Petersburg, FL 33708
PET FRIENDLY
SPECIAL OFFERPET FRIENDLY$1,875 - $2,650/mo1-2 Beds1-2 BathsSur Club Apartments | 3301 32nd Ave S,
Saint Petersburg, FL 33712
PET FRIENDLY$1,395 - $2,350/mo1-3 Beds1-2 BathsFlagler Pointe Apartments | 2540 Roy Hanna Dr S,
Saint Petersburg, FL 33712
PET FRIENDLY$1,529 - $2,319/mo1-2 Beds1-2 BathsThe Preserve at Gateway | 11800 Dr Martin Luther King Jr St N,
Saint Petersburg, FL 33716
NEW - 1 DAY AGOSPECIAL OFFERPET FRIENDLY$1,312 - $2,045/mo1-2 Beds1-2 BathsTamarind Bay Apartments | 11400 4th St N,
Saint Petersburg, FL 33716
PET FRIENDLY
SPECIAL OFFERPET FRIENDLY$1,319 - $2,188/moStudio-2 Beds1-2 BathsThe Drake at St. Pete | 1699 68th St N,
Saint Petersburg, FL 33710
SPECIAL OFFERPET FRIENDLY
SPECIAL OFFERPET FRIENDLYTotal price$1,498 - $2,808/mo1-3 Beds1-2 BathsWest Port Colony | 190 112th Ave N,
Saint Petersburg, FL 33716
PET FRIENDLY$1,650 - $3,100/moStudio-2 Beds1-3 BathsElements on Third | 3201 3rd Ave N,
Saint Petersburg, FL 33713
SPECIAL OFFERPET FRIENDLY$1,321 - $2,283/mo1-3 Beds1-2 BathsShoreline Pointe Apartments | 501 116th Ave N,
Saint Petersburg, FL 33716
SPECIAL OFFERPET FRIENDLY$1,459 - $2,018/mo1-2 Beds1-2 BathsTrellis at the Lakes | 11401 Dr Martin Luther King Jr St N,
Saint Petersburg, FL 33716
PET FRIENDLYFURNISHED
PET FRIENDLY
SPECIAL OFFERPET FRIENDLY
SPECIAL OFFERPET FRIENDLY
PET FRIENDLY
SPECIAL OFFERPET FRIENDLY
SPECIAL OFFERPET FRIENDLYFURNISHED$1,404 - $1,852/mo1-2 Beds1-2 BathsInlet Bay at Gateway | 12000 4th St N,
Saint Petersburg, FL 33716
SPECIAL OFFERPET FRIENDLY$1,250 - $1,900/mo1-3 Beds1-2 BathsPark House Apartments | 3980 64th St N,
Saint Petersburg, FL 33709
SPECIAL OFFERPET FRIENDLYFURNISHEDTotal price$2,340 - $8,018/mo1-3 Beds1-3 BathsPark & Main | 221 Main St N,
Saint Petersburg, FL 33716
SPECIAL OFFERPET FRIENDLY
PET FRIENDLY$1,075 - $1,680/moStudio-2 Beds1-3 BathsReserve at Lake Pointe Apartments and Townhomes | 5800 Lynn Lake Dr S,
Saint Petersburg, FL 33712
PET FRIENDLY
PET FRIENDLYTotal price$1,983 - $2,656/mo1-2 Beds1-2 BathsAura at 4th | 10980 Oak St NE,
Saint Petersburg, FL 33716
PET FRIENDLY$2,100 - $3,200/mo1-2 Beds1-2 BathsMarina Walk Apartments | 3680 46th Ave S,
Saint Petersburg, FL 33712
SPECIAL OFFERPET FRIENDLY
NEW - 19 HRS AGOPET FRIENDLY$2,197 - $3,363/moStudio-2 Beds1-2 BathsCottonwood Bayview | 235 3rd Ave,
Saint Petersburg, FL 33701
PET FRIENDLY
SPECIAL OFFERPET FRIENDLY
PET FRIENDLY
SPECIAL OFFERPET FRIENDLY$1,689 - $2,775/mo1-3 Beds1-2 BathsTGM Bay Isle | 11850 Dr Martin Luther King Jr St N,
Saint Petersburg, FL 33716Explore by rental type - Single Family
NEW - 7 HRS AGOAPPLY INSTANTLY
APPLY INSTANTLYFURNISHED
NEW - 10 HRS AGOPET FRIENDLY
NEW - 11 HRS AGOPET FRIENDLY
NEW - 13 HRS AGOAPPLY INSTANTLYPET FRIENDLYFURNISHEDROOM FOR RENT
NEW - 13 HRS AGOPET FRIENDLY
NEW - 15 HRS AGOPET FRIENDLY
NEW - 15 HRS AGOPET FRIENDLY
APPLY INSTANTLYPET FRIENDLY
NEW - 16 HRS AGOAPPLY INSTANTLYPET FRIENDLYFURNISHED
Explore by rental type - Townhome
NEW - 1 DAY AGOAPPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLYPET FRIENDLY
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APPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLY
APPLY INSTANTLYPET FRIENDLYFURNISHED
Explore by rental type - Condo
APPLY INSTANTLY
NEW - 9 HRS AGOPET FRIENDLY
FURNISHED
FURNISHED
PET FRIENDLYFURNISHED
FURNISHED
FURNISHED
Explore by feature - Air Conditioning
SPECIAL OFFERPET FRIENDLYTotal price$1,782 - $2,590/mo1-3 bd1-2 baCortland Brighton Bay | 10901 Brighton Bay Blvd NE,
Saint Petersburg, FL 33716
SPECIAL OFFERPET FRIENDLY$2,167 - $2,882/moStudio-2 bd1-2 baThe Exchange | 555 S Dr Martin Luther King Jr St,
Saint Petersburg, FL 33705
PET FRIENDLY
PET FRIENDLYTotal price$2,178 - $3,691/moStudio-2 bd1-2 baBeacon 430 | 430 3rd Ave S,
Saint Petersburg, FL 33701
SPECIAL OFFERPET FRIENDLY
PET FRIENDLY
SPECIAL OFFERPET FRIENDLY
SPECIAL OFFERPET FRIENDLYTotal price$2,226 - $3,031/mo1-2 bd1-2 baWaterView Echelon City Center | 100 Main St N,
Saint Petersburg, FL 33716- SPECIAL OFFERPET FRIENDLY
SPECIAL OFFERPET FRIENDLY
Explore by feature - Pet Friendly
SPECIAL OFFERPET FRIENDLY- SPECIAL OFFERPET FRIENDLYTotal price$1,782 - $2,590/mo1-3 bd1-2 baCortland Brighton Bay | 10901 Brighton Bay Blvd NE,
Saint Petersburg, FL 33716 - SPECIAL OFFERPET FRIENDLY$2,167 - $2,882/moStudio-2 bd1-2 baThe Exchange | 555 S Dr Martin Luther King Jr St,
Saint Petersburg, FL 33705 
SPECIAL OFFERPET FRIENDLY- PET FRIENDLY
- PET FRIENDLYTotal price$2,178 - $3,691/moStudio-2 bd1-2 baBeacon 430 | 430 3rd Ave S,
Saint Petersburg, FL 33701 
PET FRIENDLY$1,606 - $2,105/mo2-3 bd1-2 baBridgewater Luxury Rentals | 115 112th Ave NE,
Saint Petersburg, FL 33716- SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLYTotal price$2,226 - $3,031/mo1-2 bd1-2 baWaterView Echelon City Center | 100 Main St N,
Saint Petersburg, FL 33716
Explore by feature - Garage
- SPECIAL OFFERPET FRIENDLYTotal price$1,782 - $2,590/mo1-3 bd1-2 baCortland Brighton Bay | 10901 Brighton Bay Blvd NE,
Saint Petersburg, FL 33716 - SPECIAL OFFERPET FRIENDLY
- PET FRIENDLYTotal price$2,178 - $3,691/moStudio-2 bd1-2 baBeacon 430 | 430 3rd Ave S,
Saint Petersburg, FL 33701 - PET FRIENDLY$1,606 - $2,105/mo2-3 bd1-2 baBridgewater Luxury Rentals | 115 112th Ave NE,
Saint Petersburg, FL 33716 - PET FRIENDLY
- SPECIAL OFFERPET FRIENDLYTotal price$2,226 - $3,031/mo1-2 bd1-2 baWaterView Echelon City Center | 100 Main St N,
Saint Petersburg, FL 33716 - SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
NEW - 2 DAYS AGOPET FRIENDLYTotal price$2,047 - $3,347/moStudio-2 bd1-2 baSole on Central | 1560 Central Ave,
Saint Petersburg, FL 33705
PET FRIENDLY
Explore by rental type - Single Family
- NEW - 7 HRS AGOAPPLY INSTANTLY
- APPLY INSTANTLYFURNISHED
- NEW - 10 HRS AGOPET FRIENDLY
- NEW - 11 HRS AGOPET FRIENDLY
- NEW - 13 HRS AGOAPPLY INSTANTLYPET FRIENDLYFURNISHEDROOM FOR RENT
- NEW - 13 HRS AGOPET FRIENDLY
- NEW - 15 HRS AGOPET FRIENDLY
- NEW - 15 HRS AGOPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
- NEW - 16 HRS AGOAPPLY INSTANTLYPET FRIENDLYFURNISHED
Explore by rental type - Townhome
- NEW - 1 DAY AGOAPPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLYPET FRIENDLY
- APPLY INSTANTLY
- APPLY INSTANTLYPET FRIENDLYFURNISHED
Explore by rental type - Condo
- APPLY INSTANTLY
- NEW - 9 HRS AGOPET FRIENDLY
- FURNISHED
- FURNISHED
- PET FRIENDLYFURNISHED
- FURNISHED
- FURNISHED
Explore by feature - Air Conditioning
- SPECIAL OFFERPET FRIENDLYTotal price$1,782 - $2,590/mo1-3 bd1-2 baCortland Brighton Bay | 10901 Brighton Bay Blvd NE,
Saint Petersburg, FL 33716 - SPECIAL OFFERPET FRIENDLY$2,167 - $2,882/moStudio-2 bd1-2 baThe Exchange | 555 S Dr Martin Luther King Jr St,
Saint Petersburg, FL 33705 - PET FRIENDLY
- PET FRIENDLYTotal price$2,178 - $3,691/moStudio-2 bd1-2 baBeacon 430 | 430 3rd Ave S,
Saint Petersburg, FL 33701 - SPECIAL OFFERPET FRIENDLY
- PET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLYTotal price$2,226 - $3,031/mo1-2 bd1-2 baWaterView Echelon City Center | 100 Main St N,
Saint Petersburg, FL 33716 - SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
Explore by feature - Pet Friendly
- SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLYTotal price$1,782 - $2,590/mo1-3 bd1-2 baCortland Brighton Bay | 10901 Brighton Bay Blvd NE,
Saint Petersburg, FL 33716 - SPECIAL OFFERPET FRIENDLY$2,167 - $2,882/moStudio-2 bd1-2 baThe Exchange | 555 S Dr Martin Luther King Jr St,
Saint Petersburg, FL 33705 - SPECIAL OFFERPET FRIENDLY
- PET FRIENDLY
- PET FRIENDLYTotal price$2,178 - $3,691/moStudio-2 bd1-2 baBeacon 430 | 430 3rd Ave S,
Saint Petersburg, FL 33701 - PET FRIENDLY$1,606 - $2,105/mo2-3 bd1-2 baBridgewater Luxury Rentals | 115 112th Ave NE,
Saint Petersburg, FL 33716 - SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLYTotal price$2,226 - $3,031/mo1-2 bd1-2 baWaterView Echelon City Center | 100 Main St N,
Saint Petersburg, FL 33716
Explore by feature - Garage
- SPECIAL OFFERPET FRIENDLYTotal price$1,782 - $2,590/mo1-3 bd1-2 baCortland Brighton Bay | 10901 Brighton Bay Blvd NE,
Saint Petersburg, FL 33716 - SPECIAL OFFERPET FRIENDLY
- PET FRIENDLYTotal price$2,178 - $3,691/moStudio-2 bd1-2 baBeacon 430 | 430 3rd Ave S,
Saint Petersburg, FL 33701 - PET FRIENDLY$1,606 - $2,105/mo2-3 bd1-2 baBridgewater Luxury Rentals | 115 112th Ave NE,
Saint Petersburg, FL 33716 - PET FRIENDLY
- SPECIAL OFFERPET FRIENDLYTotal price$2,226 - $3,031/mo1-2 bd1-2 baWaterView Echelon City Center | 100 Main St N,
Saint Petersburg, FL 33716 - SPECIAL OFFERPET FRIENDLY
- SPECIAL OFFERPET FRIENDLY
- NEW - 2 DAYS AGOPET FRIENDLYTotal price$2,047 - $3,347/moStudio-2 bd1-2 baSole on Central | 1560 Central Ave,
Saint Petersburg, FL 33705 - PET FRIENDLY
What Locals Say about Chestertown
Average Rent Trends in Chestertown, MD
Rent in Chestertown, MD varies by number of bedrooms and home type. Use these charts to quickly see how rent changes.
Average rent decreased in Aug 2026 compared to the previous month. Rent previously peaked in Sep 2025.
| Month | Average rent |
|---|---|
| Sep 2025 | $2,400 |
| Oct 2025 | $2,100 |
| Nov 2025 | $2,100 |
| Dec 2025 | $2,000 |
| Jan 2026 | $1,575 |
| Feb 2026 | $1,900 |
| Mar 2026 | $2,000 |
| Apr 2026 | $2,000 |
| May 2026 | $1,520 |
| Jun 2026 | $2,050 |
| Jul 2026 | $2,000 |
| Aug 2026 | $1,920 |
Average Rent By Bedroom and Home Type
In August 2026, Apartments and Condos were the most affordable home type to rent compared with Houses.
| 1 bed | 2 beds | 3 beds | 4 beds | All | |
|---|---|---|---|---|---|
| All home types | $1,319 | $1,820 | $1,850 | — | $1,820 |
| Apartments and Condos | $1,319 | $1,820 | — | — | $1,400 |
| Houses | — | $2,400 | $1,783 | — | $1,900 |
Frequently Asked Questions about Rentals in Chestertown, MD
- What is the average rent of an apartment in Chestertown, MD?The average rent of an apartment in Chestertown, MD is $1,319 per month. This is about 33% lower than the national average.
- When is the average rent cheapest in Chestertown, MD?In the last year, the average rent in Chestertown, MD was lowest in Jan 2025 when it was $1,400 per month.
- When is the average rent most expensive in Chestertown, MD?In the last year, the average rent in Chestertown, MD was highest in Sep 2025 when it was $2,400 per month.
- How does the rent of a 1 bedroom apartment compare to a studio apartment in Chestertown, MD?The average rent of a 1 bedroom apartment in Chestertown, MD is $1,319 per month. That is about $344 more than the cost of a studio apartment.
- How many available rental listings are in Chestertown, MD?There are 7 available rental listings in Chestertown, MD.
- What are some zip codes in Chestertown, MD?
- What are some cities near Chestertown, MD?Some nearby cities include: Worton, Still Pond, Rock Hall, Church Hill, Kennedyville. These cities may have more rental options to explore.
View this page in Spanish: Chestertown, MD Apartments For Rent - 3,118 Rentals | Trulia