Holiday houses in North Shore Beach

5 out of 5 average rating, 30 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

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Condo in Chicago

4.82 out of 5 average rating, 141 reviews

Marvelous Condo w/ Pri Prkng Cls to Transit &Beach

Our 3 bedroom and 2 bathroom condo has a perfect open layout for any size group that is traveling together. You'll love the natural light. You'll have a ton of open space to share and feel at home, while also choosing from 3 bedrooms to get some privacy as well. Each bedroom has a queen size bed, while the master bedroom also has its own full size private bathroom. Feel free to stay in and cook with a fully equipped kitchen, enjoy the 55 inch Sony TV and/or gather around the very large island.

4.96 out of 5 average rating, 68 reviews

The Holiday House by the Lake! 2br/2bth

Come enjoy the holidays at this incredibly festive and modern 2 br/2 bth garden unit steps from the beach! Large kitchen, perfect for entertaining. Bth 1 has body sprays & rain head shower and Bth 2 has a jetted bath. Walking distance to local bars, restaurants, Loyola & the Red line train stop. Garage parking is avail for $25 per night. You must reserve at the time of booking by sending a request as spaces are limited. Large vehicles may not fit-please send host vehicle’s model name/size

4.97 out of 5 average rating, 124 reviews

Guesthouse in Chicago

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.

4.97 out of 5 average rating, 110 reviews

Condo in Chicago

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, 133 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

Condo in Chicago

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.

5 out of 5 average rating, 11 reviews

Apartment on the Lake

Lakeside Retreat with Stunning Views & Direct Lake Michigan Access Serene 2-bedroom, 2-bathroom apartment, complete with a private pier offering direct access to Lake Michigan. ✨ Amenities & Features: Shared outdoor terrace Onsite parking & EV charging station Steps from scenic parks—ideal for morning strolls or picnics by the lake. Prime location: Short Drive to Downtown Chicago, Wrigley Field, and top universities like Loyola University Chicago and Northwestern University.

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.

4.92 out of 5 average rating, 39 reviews

Sheridan Beach Apartment

Keep it central at this place! This basement apartment not only comes fully stocked with an in-unit washing machine, but a full kitchen with all new appliances. The unit is a PRIVATE apartment in a single-family home that is 10 steps away from the nearest CTA Bus stop, 2 blocks away from the redline, and ONLY 100 STEPS AWAY FROM THE BEACH on Lake Michigan 😄 Any and all drug use is a prohibited here. Any and all pets are prohibited here as this is a clean and newer construction.

4.92 out of 5 average rating, 36 reviews

cozy grand studio 2nd floor/near lake/public tran.

Welcome to your cozy urban retreat by the shores of Lake Michigan! Nestled in the lively neighborhood near Loyola Park, this charming studio apartment offers a delightful blend of modern comfort and vibrant city living. The decor welcoming and will create a pleasant atmosphere. Kitchen provides everything you need to prepare meals! Enjoy the sandy shores of Lake Michigan. Our convenient location offers access to public transportation, grocery stores, a variety of dining options!

4.96 out of 5 average rating, 138 reviews

Apartment in Evanston

Cozy Neighborhood Escape | Near NU-Chicago-Beaches

This is a beautiful, newly renovated apartment that is cozy and contemporary! This unit is located in Evanston’s arts district, surrounded by local shops, tree lined streets, and is a short distance to restaurants, the lakefront, and Northwestern University. Evanston is a suburb just north of Chicago with easy access to the city either by car or public transit. This apartment sleeps up to 4 people and is a 1 bedroom, 1 bath with a sofa sleeper. Don’t miss out. Book Now!

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Other great holiday rentals in North Shore Beach

4.95 out of 5 average rating, 41 reviews

Private Room in Rogers Park

NathanaelRating, 5 starstoday

Rudia and Victor are fantastic hosts. They're proactive and clear in communications of their place and their place is clean, quiet, and in a great location

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.

5 out of 5 average rating, 132 reviews

Easily accessible Uptown room

MarinaRating, 5 stars3 weeks ago

We absolutely loved starting at Cameron’s place! It was so clean, beautiful and in the perfect location for us. Cameron was so kind and helpful and really set the bar for what an Airbnb host should be. We would definitely book to stay there again!

4.98 out of 5 average rating, 93 reviews

Private Suite-Beautiful Historic Chicago Red Brick

SuzanneRating, 5 stars1 week ago

Tracy's gorgeous suite was one of my favorite airbnb's I've ever stayed at. Very tastefully decorated with all the amenities I could need. Her family is wonderful and I felt right at home in this peaceful space that a lot of love and care went into. Having a designated parking spot in the city was amazing. I'd return in a heartbeat!

4.95 out of 5 average rating, 262 reviews

Great Edgewater/Andersonville private suite

JacobRating, 5 stars2 weeks ago

Great location, great accomodations, and most importantly amazing hosts! Tripp and Todd were so welcoming, I felt right at home. They provided helpful suggestions for meals, activities, transport, etc. Hosts were in communication from the moment I landed to coordinate checkin, and allowed me to drop off my bags early when I arrived prior to the check in time. The location is great, only a few minutes walk to Clark Street which is well populated and has many restaurants and independent shops. Do yourself a favor and book with Tripp and Todd if you ever find yourself in Andersonville/Edgewater!

4.96 out of 5 average rating, 56 reviews

Rogers Park Penthouse

KendraRating, 5 stars1 day ago

The loft is picture-esque and super cozy! It has everything you need for a short stay. The location was close to public transport and we could easily walk to restaurants and bikes. The neighborhood is super cute and calm! There are winding stairs to get to the loft so if you have mobility issues or a lot of heavy luggage, think carefully! Additionally, it was too hot inside for our temperature preferences. It took hours to make it cool once we put on AC and fans. We did come on the hottest day of the year so that may be why — but again, just something to keep in mind depending on the time of year you visit. Michael was an amazingly accommodating host who gave great recommendations and offered to take us out multiple nights!

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.