Holiday rentals in Chain-O-Lakes

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Top-rated holiday rentals in Chain-O-Lakes

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

Cottage in Union Pier

4.98 out of 5 average rating, 220 reviews

"The Pines" in Union Pier: Year-round getaway

Under towering pine trees that feel more like the Northwoods, you're in the heart of Harbor Country. About 1.25 miles from the shore, minutes from New Buffalo & Three Oaks. Newly updated cabin-style home offers rustic feel with luxury comforts & highspeed WiFi, and great indoor & outdoor space. Garage plus add'l parking. Enjoy the area's beaches, restaurants, outdoor activities, breweries & wineries. Southwest Michigan at it's best! Please see policies for pets & children in house rules.

Top guest favourite

Home in Sawyer

4.96 out of 5 average rating, 79 reviews

Here and Now

Beautifully decorated home that has been featured in magazines on Interior Design. Fantastic location right next to the Warren Dunes and walking distance to the lake. Beautiful landscaping from every window. Professionally designed home features an upscale interior with a fun twist and a fabulous screened in porch. The perfect spot to enjoy a getaway in style , look no further. 2 separate buildings on the acre property , this rental is for the front building. Wi fi included but can be weak.

Superhost

Flat in New Buffalo

4.92 out of 5 average rating, 25 reviews

Charming 2BR/2BA Cottage with Full Kitchen & Patio

The cottages, or townhouses, are situated steps away from the main inn, providing an added sense of privacy while still feeling the vibe of the community. This cottage has two bedrooms (one with a queen bed in the downstairs bedroom + another with 2 twin beds in the upstairs bedroom). Two bathrooms (one upstairs, one downstairs) keep things fresh with a queen sleeper sofa. The upstairs loft space provides extra room for rest. An in-unit washer/dryer and high speed WiFi makes things easy.

Guest favourite

Home in Three Oaks

4.82 out of 5 average rating, 96 reviews

Three Oaks Creek House Perfect

3BR, 2 bath contemporary house on Spring Creek--a spawning waterway and spectacular architectural screenhouse (4th BR) at water's edge. Open floorplan, stone fireplace, gourmet kitchen and 4000CDs for spontaneous entertaining. Tempur-Pedic King master BR/office suite with lots of storage and large desk Queen 2nd BR w/standing desk, dresser, books. Full 3d BR w/ 3/4ba en-suite. Wi-fi throughout, Roku, DirecTV with HBO. Spectacular privacy, quiet and tons of specialty ameneties!

Top guest favourite

Home in Grand Beach

5 out of 5 average rating, 110 reviews

Superhost, hot tub, golf cart, fire pit, large!

Newly renovated 5 bed, 2 bath home in the quaint village of Grand Beach. Golf cart included with rental (in season - May thru mid-Nov). Home is situated on a large lot, high on a sand dune that overlooks the 6th fairway and park area. Enjoy two large decks and year-round eight person hot tub. The property is very private, on secluded street and fully stocked for a great stay. It's a great place to enjoy some down time in an idyllic village in the heart of Michigan's "Harbor Country."

Guest favourite

Home in Stevensville

5 out of 5 average rating, 13 reviews

Cozy Bluebird Cott. w/ Hot Tub!

Escape to our cozy retreat in Stevensville, MI, just minutes from Glenlord Beach Park and Lake Michigan’s stunning views. Enjoy local shops, award-winning bakeries, wineries, and golf courses nearby. Relax in the hot tub, unwind by the fire pit, or enjoy a movie night with Netflix. Our family-friendly home sleeps 5, featuring a fully equipped kitchen, outdoor deck and games. Perfect for a peaceful getaway or exploring Southwest Michigan’s best attractions. Book your stay today!

Top guest favourite

Home in Lakeside

5 out of 5 average rating, 57 reviews

Beautiful New Retreat in Lakeside - Walk to Beach

Our sunny Harbor Country home is surrounded by woods at the end of a private street and is walkable to Lake Michigan. 7-day Saturday to Saturday rental only, please. We are a 15-min walk from the Union Pier/Berrien public beach, 5-min drive from New Buffalo & Sawyer, 10-min drive from Three Oaks. There is even a pickleball court outside the front door! Occasional trains only add to the atmosphere. Owners stay on premises in their separate, upstairs studio from time to time.

Guest favourite

Home in Michigan City

4.89 out of 5 average rating, 113 reviews

Roomy and Private Getaway for Families & Friends

Perfect for Gatherings, Families, Birthdays, Group Outings: Enjoyment & Tranquility in Nature. Nestled on two acres of picturesque land, the property boasts a fully-equipped six-bedroom house. Conveniently located within a 5-minute drive to popular attractions such as the beach, casino, and outlet mall. Formerly a church, the house has been transformed into an inviting Airbnb rental, featuring a renovated interior, fire pit, gazebo, and many amenities.

Guest favourite

Cottage in Three Rivers

4.97 out of 5 average rating, 88 reviews

A hideaway retreat on a private lake for relaxing.

An extremely comfortable retreat experience for recharging yourself with water, sun, nature and quiet. This new cottage is on seven secluded acres, ideal for remote working or small reunions. The spring fed lake is wonderful for swimming, kayaking , fishing, pontooning or simply relaxing on the large decks. Kayaks, row boat, paddle boards, and pontoon INCLUDED. Ideal for introducing children to tent camping, wildlife and fishing.

Guest favourite

Flat in Michigan City

4.94 out of 5 average rating, 136 reviews

Charming apartment in Arts District

Walk to outlet mall, art galleries, parks, restaurants, and Lake Michigan beach. Walk or drive to casino. This is a 2nd-story apartment in Michigan City's historic homes. A full 1,400 sq ft of space! Fully appointed, clean and beautifully decorated. Newly renovated kitchen and bath. WIFI. Access to beautiful back yard patio and deck. Great proximity to attractions. Great for couples, solo adventurers, and families with children.

Top guest favourite

Cabin in Benton Harbor

4.99 out of 5 average rating, 267 reviews

Charming Cabin-Private Beach & Golf

Why the rave reviews? This cabin is a unique and charming 2 bedroom retreat that sits atop a hill and is surrounded by elegantly sculpted terrain of Harbor Shores golf course and walking trails. The private beach on Lake Michigan is steps away. It is located in a quiet neighborhood and is close to family fun activities in St. Joe/Benton Harbor, fantastic restaurants, wine tasting, art galleries and quaint shops.

Guest favourite

Cottage in Three Oaks

4.91 out of 5 average rating, 112 reviews

Private, Sun-filled Union Pier Cottage

Sunny, private cottage set on a half-acre facing woodlands. Quick drive to everything - beaches, hiking, restaurants, wineries, breweries, etc. High-speed internet available and desk with two monitors. Please be advised: reservation requests from first-time AIRBNB renters will be declined. You must have rented through AIRBNB in the past and received a high rating.