Vacation rentals with outdoor seating in Edgewater

Ravenswood Guest House Annex

The Annex is a private apartment in an 100+ year old wood frame home just north of Andersonville. The Annex is a typical Chicago style 'in-law' garden apartment - located on the first floor of the house where we live - it is bright and clean and well appointed with comfortable furniture. (see pictures). It has large windows that look out on our garden and yard. Our daughter's family also lives on the property in rear coach house. There is easy access to Lake Shore Drive, Evanston and downtown.

Bright & Modern Apt | Steps to Lake, Train, Food

This is the ideal location for your trip to Chicago! Steps from the Red Line Train, Foster Beach, Lake Shore Drive, Lake Front Trail, amazing Restaurants & a quality grocery store. You'll enjoy a clean & spacious 2 bedrooms apartment w/ friendly neighbors, flawless check-in & reserved parking. This place is safe & provides a beautiful & stocked apartment to relax after a busy day in the city. Short walk to Andersonville & Asia on Argyle for wonderful food options. The Riv &Aragon for concerts

Adorable Private Edgewater Suite

Cozy exposed brick, garden unit on a quiet street, perfect for relaxing after a night out in the city! Comfy, queen-sized bed, full kitchenette and gated private side entrance so its the perfect spot for your trip to Chicago! We are right by the exciting nightlife of Andersonville and a 10 minute walk to the beach/start of the Lakefront trail. Public Transit is close and easily accessible, the redline "L" can get you downtown in a half-hour train ride. Close to Loyola University, Go Ramblers!

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a new Metra stop at the end of the block and less than 10 miles from the heart of the city, your urban adventure awaits!

Walk to Foster Beach! 3 Bed Andersonville Duplex

Our charming three-bedroom duplex in trendy Andersonville is steps to Foster beach, antique shopping and so many food options. With a billiards table and wet bar in the lower level and two outdoor spaces, you may not want to leave! There are two bedrooms upstairs, one downstairs and two full bathrooms making it an ideal space for those traveling as a group or families. We're about a half-hour from the Loop on public transit and it's just a couple stops south to get to Wrigley Field-book today!

Gorgeous, cozy 1-bedroom Suite in Andersonville

Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

1910 Beautiful Restoration! Walk to Beach!

Welcome to this thoughtfully preserved 110 year old, original Chicago brick home, just 3 blocks from the Lake Michigan shoreline. Lots of charm and character in this storied home with a serene backyard oasis in the heart of the city! While this historical gem is the perfect private getaway for you & family, its location makes it easy to get around. You are: 1 Block to L train, Sushi, Thai, Coffee, Loyola 15 min: Wrigley 18 min: Downtown *We also have a 2nd unit to house a total of 16.

Private Coach house near Lincoln Square!

Lovely 625 Sq Ft detached, single-story coach house(100 years old) located in Bowmanville, nestled between Andersonville, and Lincoln Square. This little piece of heaven offers the privacy of a detached home with a fenced oversized yard perfect for puppies to run around in or enjoy a beer from one of our many local breweries. The house provides a full-size kitchen and bath with a walk Less than 1 mile to the closest CTA and 1.5 from Wrigley. Pets Allowed! Bathroom/Shower updated Feb 2025!

Andersonville Home for Groups!

Bring the whole family to this great place with lots of room. Two floors have 4 bedrooms, 2 bathrooms, 6 beds and tons of room to watch movies, play ping pong, and have a meal together. You literally cannot get closer to Andersonville center, and it’s a great home base to be not far from the lake, and Wrigleyville. The enormous back yard has fire table, and tons of room for games, kids, and dogs. We do have a strict quiet hours policy and backyard access is prohibited after 10pm.

Victorian House in Heart of Rogers Park

Newly restored Victorian house giving you a touch of Chicago's history with modern comfort. Feel at home away from home with fully equipped kitchen, entire house, and outdoor spaces with beautifully landscaped garden for lounging, grilling, and chilling. Large screen TV in living room and TVs in each bedroom. Fast Wi-Fi throughout the house. Walking distance to public transit, restaurants, bars, beach and shopping. Designated parking. #TheCatalpa

Andersonville's Secret Garden: 2 beds, 1 bath

This serene retreat is tucked away amongst the tree-lined streets of the Lakewood Balmoral historic district. Guests can venture just two blocks to dive into the hustle and bustle of Andersonville, with its incredible food scene and unique local shopping spots. Those looking to explore all that Chicago has to offer will enjoy easy access to the CTA redline, major bus routes, and Divvy stations (our shared bike provider).

Stylish 2BR Andersonville — Walk to Lake & Cafés

Steps to Chicago’s lakefront, cozy cafes, and Andersonville’s best shops. This bright 2BR blends vintage charm with fast Wi-Fi, plush bedding, and a fully stocked kitchen—ideal for couples, remote workers, and weekend explorers. Stroll tree-lined streets, explore the nearby lakefront, or curl up indoors as the seasons change. Enjoy Superhost hospitality for an effortless stay. We’d love to host your next Chicago escape.