Estia Villas - Vacation Rentals in Cheswolde
Apartment
10.0
(
7 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Hot Tub -
Parking -
Air Conditioner -
Internet
US $166
/Night
7 Nights - $1,165
Apartment
8.9
(
19 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
2002.09 ft²
-
Parking
-
Balcony/Terrace -
Air Conditioner
-
Internet
US $220
/Night
7 Nights - $1,540
Hotel
8.2
(
1003 Reviews
)
-
Parking
-
Kitchen -
Air Conditioner
-
Internet
US $163
/Night
7 Nights - $1,143
House
10.0
(
6 Reviews
)
5 Bedrooms
2 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $553
/Night
7 Nights - $3,873
Apartment
9.6
(
4 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $170
/Night
7 Nights - $1,189
House
9.4
(
31 Reviews
)
4 Bedrooms
3 Bathrooms
6 Guests
2300 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $379
/Night
7 Nights - $2,652
House
9.0
(
21 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
1792 ft²
-
Private Pool -
Hot Tub
-
Parking
-
Pool
US $389
/Night
7 Nights - $2,726
Apartment
9.0
(
4 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
750 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $161
/Night
7 Nights - $1,127
See More Cheswolde Vacation Rentals
Luxury Places to Stay in Cheswolde
Over 67+
Luxury Places to Stay in or Near Cheswolde
New
House
4 Bedrooms
3 Bathrooms
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,299
/Night
7 Nights - $9,090
House
10.0
(
6 Reviews
)
7 Bedrooms
4 Bathrooms
14 Guests
3000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $856
/Night
7 Nights - $5,993
House
8.0
(
9 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
1615 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $617
/Night
7 Nights - $4,322
House
4 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $504
/Night
7 Nights - $3,525
House
9.8
(
188 Reviews
)
3 Bedrooms
2 Bathrooms
5 Guests
1600 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $372
/Night
7 Nights - $2,603
New
House
3 Bedrooms
3 Bathrooms
8 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $344
/Night
7 Nights - $2,409
House
7.4
(
3 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $333
/Night
7 Nights - $2,330
Apartment
5 Bedrooms
3 Bathrooms
10 Guests
1292 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $332
/Night
7 Nights - $2,326
See More Cheswolde Luxury Vacation Rentals
Find More Cheswolde Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Cheswolde
Over 3+
Top-Rated Vacation Rentals with a Pool in or Near Cheswolde
Apartment
9.0
(
12 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
750 ft²
-
Parking
-
Pool
-
Kitchen
-
Air Conditioner
US $144
/Night
7 Nights - $1,010
House
6.8
(
4 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
1797.57 ft²
-
Oceanfront -
Hot Tub
-
Parking
-
Pool
US $217
/Night
7 Nights - $1,519
US $74
/Night
7 Nights - $515
Pet-Friendly Vacation Rentals in Cheswolde
Over 11+
Pet-Friendly Vacation Rentals in or Near Cheswolde
House
6 Bedrooms
7 Bathrooms
1 Guest
-
Air Conditioner
-
Internet
-
Pet Friendly -
Laundry
US $327
/Night
7 Nights - $2,291
Hotel
8.1
(
160 Reviews
)
441.32 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $143
/Night
7 Nights - $1,002
House
5 Bedrooms
2 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $175
/Night
7 Nights - $1,228
House
10.0
(
3 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $326
/Night
7 Nights - $2,284
House
10.0
(
1 Review
)
3 Bedrooms
3 Bathrooms
6 Guests
2000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $327
/Night
7 Nights - $2,289
House
5 Bedrooms
2 Bathrooms
10 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $343
/Night
7 Nights - $2,399
Apartment
2 Bedrooms
2 Bathrooms
6 Guests
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Child Friendly
US $287
/Night
7 Nights - $2,008
Apartment
3 Bedrooms
2 Bathrooms
6 Guests
1250 ft²
-
Hot Tub
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $220
/Night
7 Nights - $1,540
See More Pet-Friendly Vacation Rentals in Cheswolde on PetFriendly.io
Large Vacation Homes & Villas in Cheswolde
Over 5+
Large Vacation Homes & Villas in or Near Cheswolde
House
5.0
(
2 Reviews
)
5 Bedrooms
4 Bathrooms
10 Guests
-
Hot Tub
-
Parking
-
Internet
-
Child Friendly
US $464
/Night
7 Nights - $3,250
House
5 Bedrooms
4 Bathrooms
12 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Child Friendly
US $540
/Night
7 Nights - $3,780
House
9 Bedrooms
6 Bathrooms
9 Guests
5000 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $536
/Night
7 Nights - $3,754
US $230
/Night
7 Nights - $1,610
House
3 Bedrooms
2 Bathrooms
10 Guests
-
Kitchen
-
Air Conditioner
-
Child Friendly
-
Laundry
US $197
/Night
7 Nights - $1,379
See More Family Vacation Rentals in Cheswolde on FVR
Wheelchair Accessible Vacation Homes in Cheswolde
Over 13+
Wheelchair Accessible Vacation Homes in or Near Cheswolde
Hotel
10.0
(
1 Review
)
-
Breakfast -
Parking
-
Kitchen
-
Air Conditioner
US $126
/Night
7 Nights - $884
Hotel
7.9
(
284 Reviews
)
1146.36 ft²
-
Breakfast
-
Parking
-
Air Conditioner
-
Internet
US $124
/Night
7 Nights - $867
Hotel
8.0
(
1003 Reviews
)
-
Breakfast
-
Parking
-
Kitchen
-
Air Conditioner
US $128
/Night
7 Nights - $893
Hotel
7.0
(
2 Reviews
)
-
Breakfast
-
Parking
-
Kitchen
-
Air Conditioner
US $128
/Night
7 Nights - $898
US $128
/Night
7 Nights - $898
US $128
/Night
7 Nights - $898
Condo
5.0
(
4 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $193
/Night
7 Nights - $1,351
US $1,138
/Night
7 Nights - $7,963
Cheswolde Vacation Rentals and Airbnb Places to Stay Under $200
Over 20+
Cheswolde Vacation Rentals and Airbnb Places to Stay Under $200
House
1 Bedroom
1 Bathroom
2 Guests
-
Internet
-
Bedding/Linens -
Security/Safety
US $106
/Night
7 Nights - $743
US $90
/Night
7 Nights - $630
US $106
/Night
7 Nights - $740
House
4 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Internet
-
Child Friendly
-
Laundry
US $160
/Night
7 Nights - $1,118
Apartment
10.0
(
6 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $149
/Night
7 Nights - $1,040
House
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1700 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $163
/Night
7 Nights - $1,141
Apartment
8.0
(
4 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Kitchen
US $127
/Night
7 Nights - $889
Apartment
6.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
-
Air Conditioner
-
Child Friendly
US $79
/Night
7 Nights - $553
See More Cheswolde Vacation Rental Deals
Instantly Bookable Vacation Homes in Cheswolde
Over 14+
Instantly Bookable Vacation Homes in or Near Cheswolde
House
8.0
(
2 Reviews
)
4 Bedrooms
2 Bathrooms
6 Guests
1800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $512
/Night
7 Nights - $3,587
House
4 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $412
/Night
7 Nights - $2,886
Apartment
2 Bedrooms
1 Bathroom
7 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $242
/Night
7 Nights - $1,696
House
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $224
/Night
7 Nights - $1,568
Apartment
2 Bedrooms
1 Bathroom
4 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $224
/Night
7 Nights - $1,567
House
3 Bedrooms
1 Bathroom
6 Guests
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
US $217
/Night
7 Nights - $1,516
House
3 Bedrooms
3 Bathrooms
3 Guests
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
US $154
/Night
7 Nights - $1,079
House
2 Bedrooms
1 Bathroom
3 Guests
-
Parking
-
Kitchen
-
Internet
-
Child Friendly
US $120
/Night
7 Nights - $840
About Cheswolde Vacation Rentals
With more than 76 Cheswolde vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Cheswolde.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Cheswolde, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Cheswolde. Places to stay near Cheswolde are 490.78 ft² on average, with prices averaging US $302 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Cheswolde with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Cheswolde
| Type | Count |
|---|---|
| Vacation Homes | 41 |
| Holiday Apartments | 18 |
| Hotels | 16 |
Use these Quick Filters to Find a Vacation Rental in Cheswolde
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Cheswolde.
Weather in Cheswolde
View the weather forecast for Cheswolde before booking your Cheswolde Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Cheswolde, MD
Estiavillas offers a large selection of top attractions around Cheswolde. Research things to do on your vacation before you visit Cheswolde.
National Aquarium in Baltimore
Baltimore Cruise Terminal
Johns Hopkins University
Baltimore Convention Center
Johns Hopkins Hospital
Horseshoe Casino Baltimore
Baltimore Inner Harbor Marina
Arundel Mills Mall
M&T Bank Stadium
Oriole Park at Camden Yards
Maryland Live Casino
Towson University
Maryland Zoo
Merriweather Post Pavilion
Power Plant Live
Hippodrome Theatre
Baltimore Museum of Art
University of Maryland - Baltimore
Towson Town Center
White Marsh Mall
Cheswolde Vacation Rental Frequently Asked Questions
Which vacation homes in Cheswolde are best for families?
If you are looking for a family-friendly vacation home in Cheswolde, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cheswolde:
How many vacation rentals are available in Cheswolde?
Currently, the total number of properties listed in 2026 is over 76 in the Cheswolde area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Cheswolde.
