Holiday houses in Rogers Park, Chicago

5 out of 5 average rating, 141 reviews

Spacious 3BR with Parking Option, Steps to Metra!

Newly renovated, the Greenleaf is the entire second floor of a two-flat on a residential street. It has been thoughtfully designed for comfort and convenience. Great location for Loyola and Northwestern University visits or downtown sight-seeing. The Metra stop for trains to the Loop or the North Shore suburbs is ON OUR BLOCK. Lake Michigan free beaches are a mile away. Easy walk to a variety of small restaurants or 10-minute drive to Evanston or Andersonville for amazing dining and shopping.

4.84 out of 5 average rating, 213 reviews

Cozy Northside Apt near Transp&Beach&Free St Prkng

PRIVATE Entrance, One Bedroom Apt w/ LVG RM near Lake Michigan in beautiful, residential & diverse neighborhood. FREE on street PARKING, OR driveway spot for Addt fee. Sleeps up to 6. *It has a Kitchenette, Full Bath, WiFi, Cable TV, in unit W/D. Close to METRA TRAIN (1 block & 18 min to loop/city center), Bus Stop 1 block & the CTA "L" (elevated) Red Line to City 7 blocks away. Enjoy our proximity to Public Transit, Beaches, Loyola & NW Universities. Great for family, friends & kids.

Guesthouse in East Rogers Park

4.97 out of 5 average rating, 124 reviews

A bit of the North Woods on Chicago's North Side!

Looking to get away from it all but not TOO far away? Ours is a quiet, screen-free property perfect for a writer’s or artist’s retreat. NU/Loyola parents or alums, stay here when you visit your kids/alma mater. Fantastic renovated livery barn with lots of light, privacy and amenities. Located in Rogers Park, a short walk to Metra and the Red line. Ample street parking nearby. Created for comfort with a splash of Swedish design, enjoy the deck overlooking a tree-filled garden and waterfall.

4.93 out of 5 average rating, 28 reviews

Spacious & Elegant N Side Apt Near Beach & Transit

This spacious 1-bedroom apartment, just 1 minute from Marion Majony Griffin Beach, offers comfort and convenience for solo travelers, couples, or small families. Enjoy a fully equipped kitchen, cozy pull-out couch, and a dedicated workspace perfect for remote work or studying. Free street parking is available, or take public transit just a block away to the Red Line for easy access to the city. With its prime location and thoughtful amenities, we warmly welcome all travelers to our listing.

4.98 out of 5 average rating, 109 reviews

The Ramblers Inn, Northside NEW Reno w/parking!

Our family 2-flat has been completely gutted to the studs renovated with new everything! This top floor 3 bed 1 bath home has CENTRAL A/C, in unit washer/dryer, and free parking on-site. This prime location is a short walk to Loyola University, beaches/playgrounds, public transportation and award-winning restaurants. Lake shore trail is less than a mile away. We are steps away from a large local grocery store. Your urban stay will feel like a relaxing retreat because of these conveniences.

5 out of 5 average rating, 132 reviews

Remodeled, Near Loyola, Beach and Subway

Stylish and sophisticated, this remodeled 3 bedroom, 2 bath private apartment is in a prime location, 3 blocks from Hartigan Beach, and 2 blocks to the Loyola Red Line "L" station to take you to Wrigley Field, downtown & many locations in between. We are 2 blocks from Loyola University & about 4 miles to Northwestern University. Located on a quiet, residential tree-lined street, we are a 2 block walk from all manner of restaurants & conveniences associated with our proximity to Loyola.

4.97 out of 5 average rating, 60 reviews

Jarvis Gardens - 1BR/BEACH/Wine patio/fire pit

Welcome to Jarvis Gardens. A hidden gem in the heart of Chicago's Rogers Park northside neighborhood, located 8 miles north of downtown. Live like a true Chicagoan in this beautifully appointed and recently renovated apartment. Just 1 block to Lake Michigan's Jarvis beach, 1/2 block to Jarvis Square (shops/restaurants/bars/wine stores), and the Jarvis Redline train to Wrigley Field or the 147 bus to the famed Michigan Avenue shopping. No car is necessary for this vacation destination.

4.88 out of 5 average rating, 296 reviews

Beautiful Three Bedroom Apartment Near Loyola

Welcome to our beautiful 3 bedroom apartment just blocks from Loyola University. Fully furnished apartment with one queen bed, two full beds, and one pull-out futon. Amenities include full kitchen, dining room, and 2 bathrooms. WiFi, cable, 3 televisions throughout the apartment and sunroom and back yard too! Close to public transportation, the lake, and dozens of dining options within walking distance. One (1) City Street Parking Pass will be provided for each night of your stay.

4.91 out of 5 average rating, 64 reviews

1 bedroom apt near Michigan Lake

Escape to your urban oasis by the shores of Lake Michigan! This charming one-bedroom apartment is your haven in the heart of the vibrant Loyola Park neighborhood. Unwind in a cozy retreat that blends modern comforts with the energy of city living. Savor the warmth of the inviting decor and cook up a storm in the well-equipped kitchen. Step out to revel beaches of Lake Michigan and enjoy effortless access to public transport. Come to relaxation and excitement-all in one!

4.99 out of 5 average rating, 288 reviews

Cozy 3BR on Chicago's North Side & Free Parking

Enjoy this charming 3-bedroom condo with free on-site parking just three blocks from Lake Michigan. Convenient access to public transit, including the express bus to downtown (9 miles), Navy Pier, and Grant Park. The CTA Jarvis station is only three blocks away. Perfect for families, business travelers, and couples, this condo is also close to Loyola (1.5 miles) and Northwestern universities (2.5 miles). A great home base to explore all that Chicago has to offer!

4.93 out of 5 average rating, 241 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This cozy AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed, TV, dining table, & partial kitchenette. NOTE: No full kitchen.

4.98 out of 5 average rating, 100 reviews

Home in East Rogers Park

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

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Other great holiday rentals in Rogers Park, Chicago

4.95 out of 5 average rating, 41 reviews

Private Room in Rogers Park

HenryRating, 5 stars6 days ago

Victor and Rudia are very communicative and provide clear instructions. The room is clean, and I had an enjoyable stay!

Private room in West Rogers Park

4.99 out of 5 average rating, 153 reviews

At the junction of comfort and care

KristinaRating, 5 stars1 month ago

William is an amazing host who is very accommodating and helpful with all questions relating to parking and transit to downtown Chicago. He was very responsive to all my communications and was clear on expectations. Fantastic person and place!

4.97 out of 5 average rating, 105 reviews

The Stained Glass Apt. Edgewater #2

SandraRating, 5 stars1 week ago

I loved Felice’s home. It is decorated with great taste and artistry. The house is quiet, all the spaces are uniquely decorated, the kitchen is a wonderful work of craftsmanship, and although my room was small, it is very comfortable. I slept well. The area is very walkable and pretty, with lots of lined trees on the neighborhood streets. It is close to neighborhood shops and walking distance to the lake. Felice is a wonderful host. She is accesible and very friendly. She made me feel right at home.

4.98 out of 5 average rating, 52 reviews

Renovated Sunny Oasis Steps From the Lake

Henry A.Rating, 5 stars1 week ago

OMG Tammy was the best hostess. She and the whole family had me feeling right at home. As time progressed, I felt even more at home, each of us learning more of the other. I received great local advice from she and Scott, her husband… which by the way saved me lots in parking fees. Was escorted to a local market… and was advised by Scott’s mom to go to the lake right away to see the most beautiful moonrise. Meals were shared, information of all kinds of subjects were exchanged, and even motivation given. I would have no reservation staying with Tammy and the crew in the future.

4.91 out of 5 average rating, 137 reviews

Short stay-Warm and Cozy room in Beautiful Condo

SwaroopRating, 5 stars4 months ago

Barbara & James have been excellent hosts. They are kind, friendly and mindful, and overall incredible people. They have immediately made me feel welcome in their home and were ready to help every step of the way in the transition to my new life in Chicago. I had a comfortable stay in a clean and cozy home. I had a great time here. I cannot recommend Barbara’s place highly enough.

4.96 out of 5 average rating, 55 reviews

Rogers Park Penthouse

TaylorRating, 5 stars1 day ago

I absolutely loved my stay! Michael was super helpful for a first time traveler to the city. He assisted me with my bags and would always check in on how everything was going. I really appreciated the hospitality. Definitely will keep Michael's place in mind when I visit again.

Private room in North Park

4.97 out of 5 average rating, 38 reviews

Lovely master bedroom with private bath

LenaRating, 5 stars2 weeks ago

The apartment was beautiful and comfortable along with being in a nice spot just outside of downtown. Samuel was also very friendly and accommodating which is a definite plus! I would definitely stay with him again.