Holiday rentals with a kayak in Berrien County

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.

Location · Outdoor spaces · Access

Cabin with POOL in family resort!

Nestled within a gated 67-acre resort and just minutes from the shores of Lake Michigan, this charming cabin offers a peaceful retreat ideal for couples, families, or solo travelers, blending rustic décor with modern comforts. Guests can spend their days exploring nearby nature trails, lounging by the pool, paddling across the lake, or unwinding on the porch. The perfect vacation for exploring nearby orchards and countryside, catching live music or theater, or just slowing down and recharging!

Location · Value · Cleanliness

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!

Location · Outdoor spaces · Air conditioning

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.

Location · Outdoor spaces · Quiet

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.

Value · Outdoor spaces · TV

Riverfront Oasis with Private Boat Dock

Welcome to your Riverfront Getaway – Escape to this charming two-bedroom riverfront retreat, where relaxing water views are always within reach. Enjoy your morning coffee or evening sunsets from the spacious decks overlooking the river. Unwind on the large patio or bring your boat and take advantage of the private dock. Perfect for couples, families, or friends looking for a peaceful waterfront getaway with all the comforts of home. Firepit and outdoor dining by the water. Book your stay today!

Location · Outdoor spaces · Hot tub

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.

Value · Location · Hospitality

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.

Location · Outdoor spaces · Check-in

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!

Location · Outdoor spaces · Kitchen

Updated Cozy Cottage Near Lakes, Wineries & Trails

Deer Cottage is a warm and cozy retreat near Big & Little Paw Paw Lakes—perfect for a romantic getaway or family stay. This renovated lake home sleeps 4 with a queen bed and sleeper sofa, a fully remodeled kitchen and bath, indoor gas fireplace, and 2 smart TVs. Just a short drive away, guests can explore nearby wineries, kayak the river, or relax at Lake Michigan. Indy grandparents created this sweet escape to be near their granddaughters—complete with deer sightings right from the yard.

Location · Outdoor spaces · Comfort

Sun Sand and Tee Times

Located in the SW Michigan beach community of Harbor Shores, this property overlooks the 6th hole of the award winning Harbor Shores Golf Club, a Jack Nicklaus design. Just minutes from Jean Klock Beach & the iconic North Pier Lighthouse at Tiscornia Park. Miles of scenic walking and biking paths begin right outside your front door. Not to mention kayaking and paddleboarding on the Paw Paw river. This 4 bdr home is perfect for those who love the outdoors and want the comforts of home.

Outdoor spaces · Location · Quiet

Wrap-Around Beach Bunker/Autumn getaway

Enjoy nature at its finest, a beautiful custom built home complete with all modern amenities, our place is a perfect year-round, wooded retreat. You'll love the huge wraparound front porch with ample seating. The gourmet kitchen flows into the living room for entertaining. The ample basement living area is a great game room for the kids. We are close to Lake Michigan beaches, restaurants, shopping and family activities. Perfect for large families, or friends wanting to stay together.

Outdoor spaces · Location · Nearby