Holiday rentals in New Trier Township

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Top-rated holiday rentals in New Trier Township

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Top guest favourite
The ranch style home is set against a backdrop of vibrant autumn foliage. A large tree with orange leaves stands prominently in the front yard, complemented by well-maintained landscaping. A driveway leads to an attached garage, while outdoor seating is visible on a neatly manicured lawn.
Home in Northbrook
4.98 out of 5 average rating, 124 reviews

*King bed *Outdoor Living *Sought-After Area

Welcome to our sophisticated ranch style home, nestled in the serene, central Chicago neighborhood of Northbrook. This carefully curated home offers a peaceful retreat in a walkable neighborhood with nearby shopping and dining. With its elegant decor, comfortable furnishings, and modern amenities, the home provides a haven of relaxation. Whether you're enjoying a cup of coffee on the private patio or exploring the area, this home provides the perfect backdrop for a memorable vacation experience.

Top guest favourite
Home in Wilmette
4.98 out of 5 average rating, 204 reviews

Unique porcelain-enamel paneled "Lustron" home

This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

Top guest favourite
Flat in Evanston
4.99 out of 5 average rating, 107 reviews

Evanston 2BR 2Bth 1 Blk to Beach

With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

Guest favourite
Flat in Evanston
4.91 out of 5 average rating, 181 reviews

New 3bd/1.5 bth Apt w/private prkg

A perfect hideaway! This quiet, secluded unit is nestled in lush greenery within walkng dist (1.5M) to NWU. Enjoy our renowned restaurants and theaters, plus easy access to downtown Chgo’s many attractions via the Metra; Sleeps up to 7 guests, with 2 queen beds, 2 single beds, and an 8-foot couch in Liv rm; Ultra-modern kitchen equipped with everything; Dedicated parking space in rear of the bldng; free high-speed Wi-Fi is included. Host lives nearby and responds promptly to any inquiries

Top guest favourite
The exterior entrance features a spacious covered porch with a stone pathway leading to a set of glass doors. Surrounding greenery, including hanging flower pots and blooming plants, enhances the welcoming aesthetic of the house.
Guest suite in Riverwoods
4.95 out of 5 average rating, 479 reviews

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

Top guest favourite
A circular cedar hot tub is set on a wooden deck, surrounded by greenery and sunlight filtering through trees. Nearby, two chairs and a table are positioned beside a potted plant, providing a cozy relaxation space. Bamboo privacy screens add a touch of seclusion.
Treehouse in Schaumburg
4.94 out of 5 average rating, 872 reviews

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

Guest favourite
The historic manor house features a rich red brick facade adorned with lush green ivy. The spacious porch extends from the building, complemented by well-maintained gardens that enhance the inviting exterior. Large windows provide ample natural light, creating an open and airy ambiance.
Guest house in Evanston
4.93 out of 5 average rating, 134 reviews

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house.

Top guest favourite
The exterior of the house features a charming two-story structure with light-colored siding and blue doors. A welcoming front porch is adorned with red, white, and blue bunting. Lush green landscaping surrounds the entrance, with flower beds contributing to the inviting scene.
Flat in Evanston
4.97 out of 5 average rating, 540 reviews

Charming, Sunny Apartment with Backyard Garden

House of the Blue Doors Enjoy staying with us in this spacious 1st floor flat. Furnished by the resident designer in tasteful neutrals, original curated artwork, one of a kind furniture and accent pieces. Sip morning coffee or a glass of wine in the sunlit kitchen or front porch, fire up the backyard grill for a barbecue. Soak in the award winning Chicago ceramic artist designed and made floor in the bathroom. Close to Northwestern, Chicago, Lake Michigan, everything Evanston offers.

Guest favourite
A private backyard oasis features a green lawn bordered by vibrant yellow flowers. A small path winds through the garden, leading to a door set into a light-colored wall. A decorative planter sits on a stone pedestal, and wooden trellises are visible in the background.
Home in Evanston
4.87 out of 5 average rating, 226 reviews

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

Guest favourite
Flat in Evanston
4.94 out of 5 average rating, 160 reviews

NEW Fam-Frndly 3 bd 1 bth w/ EZ Parking near NU

Relax with the whole family or explore the city at this peaceful newly renovated 3bd/1bth apartment with plenty of free parking and in-unit washer/dryer. You’ll be close to everything when you stay at this centrally-located place. Only 2 mins from DT Evanston and 25 mins from DT Chicago! Just mins away from Northwestern and Loyola Universities. Enjoy the 65in and 55in Smart TVs, listen to your favorite tunes w/ the voice enabled Amazon Echo Alexa speaker, or enjoy family games.

Top guest favourite
The historic home exterior is showcased, featuring a vibrant red facade with white accents. A charming porch adorned with lattice and railings provides an inviting entrance. Lush greenery surrounds the property, complemented by a white picket fence and vibrant landscaping.
Flat in Wilmette
4.9 out of 5 average rating, 294 reviews

Spacious Garden Apartment with Sauna and Fireplace

English garden apartment in historic Wilmette home with a private entrance, sauna, washer/dryer, kitchenette, dining area, recreation room with pool table, vintage pinball machine, and a wood-burning fireplace with gas igniter. Two queen beds, 1 full-size sleeper sofa, and a single mattress are available for large families. Ideal access to Northwestern University for all events. **Please note the apartment is located on the garden level and does NOT include the entire home.**

Top guest favourite
Apartment in East Rogers Park
4.99 out of 5 average rating, 299 reviews

Your Chicago Retreat

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!

Popular amenities for New Trier Township holiday rentals