Holiday rentals with a kayak in Berrien County

Sunrise Cottage on Clear Lake!

Welcome to Sunrise Cottage on Clear Lake! This 1960s charmer features knotty pine walls, vaulted ceilings, a cozy wood-burning fireplace, and a fully stocked eat-in kitchen. With two queen bedrooms, a shower bath, and a limestone patio with a gas grill and firepit, it’s the perfect retreat for couples, small families, and bring your pup! In the winter, it transforms into a magical wonderland—perfect for cozy fireside evenings and snowy adventures. Relax, explore, and make unforgettable memories!

Relax on the shores of Lake Chapin

Beautiful private self-contained Guesthouse on the shore of Lake Chapin all sports lake. Enjoy our kayaks, paddle boat & canoe. Play in the water or relax on a float just steps from the back door. New furniture & Kitchen Remodeling completed. Enjoy the fire pit or relax and watch the beautiful scenery. Enjoy the walk out deck with a wonderful view of the lake. Morning coffee with the wildlife or evening tea watching the sunset. 2022 Brand New Central A/C Installed. Pets welcome for a small fee.

Riverfront Oasis with Private Boat Dock

Welcome to your Riverfront Getaway - 40 minutes from Notre Dame stadium! Nestled on a quiet stretch of the river, our home offers the perfect blend of serenity and accessibility. Whether your coming for a Fighting Irish game, a weekend on the water, or just a peaceful retreat, you'll love what our space has to offer! River Life Perks - Private Boat/Jet ski docks (kayaks provided). Peaceful decks for morning coffee or evening drinks. Firepit and outdoor dining by the water. Book your stay today!

FARM 10 acres, pond, Hot tub, king bed 30 min ND

Come to the farm for peace, quiet, nature walks, bird watching, and fishing in the spring-fed 3-acre pond and find a new sense of calm. All you need is to build a fire, then sit back and relax. Winter or summer, the farm offers 10 acres of space to run around with your pups or bags, frisbee, and even a bit of golf. Kayak or canoe, too! So many wineries, bike trails, and parks are close by. End your day with a relaxing, stargazing hot tub overlooking the pond. Enjoy! 10 min east of Three Oaks.

Dog-Friendly Lake-View Cottage Near Wineries

Less than 2 hrs from Chicago & a short walk to Little Paw Paw Lake, enjoy the charming vibes of our quaint and completely private cottage. With a stunning view of the lake, indoor/outdoor fire areas, and a serene yard, our home is perfect for a weekend away, a Michigan staycation, or even as an overflow home when visiting family. Our cottage exudes old charm with its rustic hardwood floors and cabin-like porch, yet it has the right amount of modernity with high-speed WiFi and newer appliances.

Quiet Walk to Lake Michigan Beach - Seaside Smores

So close to Chicago and yet in a world of its own! Adorable two bedroom cottage is located on a quiet wooded lane about a half-mile walking distance to the world class beach on Lake Michigan. Enjoy nearby park with playground, basketball, volleyball, and tennis courts, performing arts theatre, horseback riding stables, golf course, and more - all within a block or two of the cottage. See our other nearby listings, too! Relax in simple comfort — you made a great choice to stay at the cottage.

Heron's Rest Hideaway, nature lovers' dream

Privacy on 11 acres of conservancy-protected land including two lakes, river access, woods. Rowboat available. Fishing on site. Nature lovers dream! Minutes from Michigan’s most popular beach, breweries, wineries, antique malls, farm-to-table restaurants. Fully equipped kitchen, gas fireplace. Private fire pit, deck, and gas grill. Kayak, bike, hike nearby. Separated from our home by a breezeway. Private entrance, quiet road, dark nights. Daytime woodworking noise possible. Limit of 4 guests.

4 Bedroom home w/pool in St. Joseph

This home is all about having fun with the family. Open concept kitchen, living room & dining room. Deck off the dining for eating al fresco. Family room & game room area with large screen TV, Nintendo switch, game table with lots of board games & a dart board. Walkout to the pool (unheated) and fire pit area for fun in the sun and evening campfires to roast marshmallows. Outdoor games include bag toss, ladder ball, ring toss. Home is five miles to Silver Beach and downtown Saint Joseph.

Hot tub! Starlight cottage in Lakeside!

Feel relaxed, refreshed, & recharged! Our home is the perfect blend of comfort & cottage charm!Home is 2450 sq. ft., 3 bdrm,3 bth (2 BR, 2 BA in main home),updated & features a full kitchen, laundry room,6 TV’s,WiFi, & 2 eating areas.Attached guest apt. has 1 bdrm,1 bth upstairs w/ full kitchen,w/d,king bed, kids cubby w/ queen size gel mattress, & 2 TV’s.Guest apt. is attached & is perfect for people in your party requiring privacy!Close to everything but “socially distanced” in Lakeside!

Historic 2 bedroom converted church on Lake MI

Spend your holidays at the lake! We cooked (not really), we decorated (really), we made it nice (definitely). Less than a quarter mile away from Lake Michigan, this 2500 square foot, 100 year old church has been converted to include two bedrooms, one bathroom, full kitchen, and a large, open living area. Located between St. Joseph and South Haven with a dozen public beaches along the stretch. Feel remote while being close to everything! Off season guests can access the private beach.

Riverfront Haven: Hot Tub, 5 Beds, Kayaks & More

RiverEdge is a luxury riverfront retreat on the St. Joseph River, perfect for families and groups of up to 10 guests. Enjoy a private, peaceful setting with upscale amenities, cozy indoor spaces, and scenic river walks—ideal for weekend getaways or extended stays. Enjoy cozy evenings inside or venture out for refreshing river walks. Whether it’s a 2-day getaway or a 30-day stay, RiverEdge promises a winter experience filled with warmth, relaxation, and cherished family moments.

Pool, Hot tub, Kayaks, Waterfront, SW Michigan

Waterfront property with a private hot tub, pool, and tennis court, making it an ideal destination for those seeking both relaxation and recreation. Visit beautiful Southwest Michigan and stay at the St. Joe Overlook. Take a swim in the pool, unwind in the hot tub, take the kayaks out for a river cruise, or sit by the fire. Enjoy this stunning location and top-notch amenities. A trip to the St Joe Overlook is the perfect place to gather & reconnect. Maximum Guest Count 16.