Holiday rentals near Chesapeake Employers Insurance Arena
We found 1,070 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of Chesapeake Employers Insurance Arena, scroll through and discover holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the amenities that you need and want, which might include parking and a fireplace. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Chesapeake Employers Insurance Arena
Showing deals for:7 Nov - 14 Nov
Image gallery for Rare find! Chic cottage, salt water heated pool May 15-Oct15.
1010 out of 10 rating
Exceptional
(52 reviews)
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Arnold, MD
12% off
Price is S$7,576
S$7,576
S$1,082 per night
includes taxes & fees
Image gallery for Welcome to our newly built house
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Welcome to our newly built house
Glen Burnie, MD
8% off
Price is S$3,767
S$3,767
S$538 per night
includes taxes & fees
Image gallery for Annapolis Entertainment Complex
1010 out of 10 rating
Exceptional
(90 reviews)
Annapolis Entertainment Complex
Arnold, MD
8% off
Price is S$6,831
S$6,831
S$976 per night
includes taxes & fees
Image gallery for Chesapeake Cottages- 2 Quaint Waterfront Retreats
9.69.6 out of 10 rating
Exceptional
(22 reviews)
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena, MD
8% off
Price is S$4,496
S$4,496
S$642 per night
includes taxes & fees
Image gallery for Mins to Annap; Luxury Townhome
1010 out of 10 rating
Exceptional
(5 reviews)
Mins to Annap; Luxury Townhome
Arnold, MD
7% off
Price is S$5,055
S$5,055
S$722 per night
includes taxes & fees
Image gallery for Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
1010 out of 10 rating
Exceptional
(22 reviews)
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
Severna Park, MD
7% off
Price is S$4,056
S$4,056
S$579 per night
includes taxes & fees
Image gallery for The Santi Paradise
1010 out of 10 rating
Exceptional
(15 reviews)
The Santi Paradise
Glen Burnie, MD
8% off
Price is S$7,238
S$7,238
S$1,034 per night
includes taxes & fees
Image gallery for Airy & Spacious Modern Farmhouse
9.69.6 out of 10 rating
Exceptional
(30 reviews)
Airy & Spacious Modern Farmhouse
Reisterstown, MD
33% off
Price is S$6,173
S$6,173
S$882 per night
includes taxes & fees
Image gallery for The GRACE Villa - a homey affair!
8.68.6 out of 10 rating
Excellent
(18 reviews)
The GRACE Villa - a homey affair!
Reisterstown, MD
14% off
Price is S$5,129
S$5,129
S$733 per night
includes taxes & fees
Image gallery for Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio
1010 out of 10 rating
Exceptional
(5 reviews)
Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio
White Marsh, MD
12% off
Price is S$3,653
S$3,653
S$522 per night
includes taxes & fees
Image gallery for Annapolis waterfront "tiny house" in garden setting
1010 out of 10 rating
Exceptional
(236 reviews)
Annapolis waterfront "tiny house" in garden setting
Annapolis, MD
8% off
Price is S$1,537
S$1,537
S$220 per night
includes taxes & fees
Image gallery for Modern Smart Home w/Gourmet Kitchen, Peloton & King Suite with Rooftop Deck
1010 out of 10 rating
Exceptional
(5 reviews)
Modern Smart Home w/Gourmet Kitchen, Peloton & King Suite with Rooftop Deck
Baltimore, MD
8% off
Price is S$9,972
S$9,972
S$1,425 per night
includes taxes & fees
Image gallery for ✨ Stunning ✨ 7BR Lux House in Baltimore
1010 out of 10 rating
Exceptional
(6 reviews)
✨ Stunning ✨ 7BR Lux House in Baltimore
Baltimore, MD
8% off
Price is S$7,227
S$7,227
S$1,032 per night
includes taxes & fees
Image gallery for Beautifully Renovated row House in Trendy Canton, private parking driveway
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Beautifully Renovated row House in Trendy Canton, private parking driveway
Baltimore, MD
14% off
Price is S$2,685
S$2,685
S$384 per night
includes taxes & fees
Image gallery for Stylish 4-bedroom whole house with plenty of parking
9.29.2 out of 10 rating
Wonderful
(24 reviews)
Stylish 4-bedroom whole house with plenty of parking
Catonsville, MD
8% off
Price is S$3,520
S$3,520
S$503 per night
includes taxes & fees
Image gallery for New luxury apartment in Baltimore City near JHU and the heart of Hampden
1010 out of 10 rating
Exceptional
(12 reviews)
New luxury apartment in Baltimore City near JHU and the heart of Hampden
Baltimore, MD
11% off
Price is S$1,370
S$1,370
S$196 per night
includes taxes & fees
Image gallery for Rock Creek Cottage, Waterfront, Serene Views
1010 out of 10 rating
Exceptional
(6 reviews)
Rock Creek Cottage, Waterfront, Serene Views
Pasadena, MD
7% off
Price is S$2,557
S$2,557
S$365 per night
includes taxes & fees
Image gallery for 6 Mi to Inner Harbor - Family Home w/ Fenced Yard!
1010 out of 10 rating
Exceptional
(15 reviews)
6 Mi to Inner Harbor - Family Home w/ Fenced Yard!
Baltimore, MD
12% off
Price is S$2,152
S$2,152
S$307 per night
includes taxes & fees
Image gallery for Waterfront Apartment with Fantastic Views
1010 out of 10 rating
Exceptional
(162 reviews)
Waterfront Apartment with Fantastic Views
Pasadena, MD
17% off
Price is S$1,816
S$1,816
S$259 per night
includes taxes & fees
Image gallery for Spacious Private Basement
1010 out of 10 rating
Exceptional
(6 reviews)
Spacious Private Basement
Severn, MD
8% off
Price is S$1,045
S$1,045
S$149 per night
includes taxes & fees
Image gallery for A Unique & Private Single Family Home with 5 acres of privacy.
9.69.6 out of 10 rating
Exceptional
(64 reviews)
A Unique & Private Single Family Home with 5 acres of privacy.
Cockeysville, MD
12% off
Price is S$5,739
S$5,739
S$820 per night
includes taxes & fees
Image gallery for Beautiful New Renovated Home on 3 Acres Between Annapolis/DC/Balt
1010 out of 10 rating
Exceptional
(6 reviews)
Beautiful New Renovated Home on 3 Acres Between Annapolis/DC/Balt
Gambrills, MD
11% off
Price is S$2,855
S$2,855
S$408 per night
includes taxes & fees
Image gallery for Pasadena, MD close to Annapolis/WDC/Baltimore
1010 out of 10 rating
Exceptional
(35 reviews)
Pasadena, MD close to Annapolis/WDC/Baltimore
Pasadena, MD
14% off
Price is S$2,551
S$2,551
S$364 per night
includes taxes & fees
Image gallery for Big 3 story house near stadiums, aquarium, museums, 5 bedrooms, parking
1010 out of 10 rating
Exceptional
(16 reviews)
Big 3 story house near stadiums, aquarium, museums, 5 bedrooms, parking
Baltimore, MD
8% off
Price is S$4,920
S$4,920
S$703 per night
includes taxes & fees
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Find the best place to stay - Chesapeake Employers Insurance Arena
Charming 3-bedroom townhome with AC, WiFi in marvelous Baltimore
Sleeps 6 · 3 bedrooms · 1 bathroom
Charming townhome with WiFi and fitness room in lovely Woodlawn
Sleeps 2 · 1 bedroom · 1 bathroom
7.47.4 out of 10
Goodgood
3 reviews(3 reviews)
Top floor palace #3
Sleeps 6 · 3 bedrooms · 1 bathroom
Delightful 4-Bed Whole House with Easy Parking
Sleeps 8 · 4 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Federal Hill - Central, fully renovated townhouse. Close to restaurants and bars
Sleeps 90 · 2 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
The Baltimore Nest, Stadium Walkable, Big Rowhouse
Sleeps 10 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value