Pet-friendly holiday rentals in Sawyer

-The District 5 Schoolhouse-

The District 5 Schoolhouse was historically built "with not a single nail in the structure" in the 1800's. It still stands as a symbol of dedication to craftsmanship and community. Lovingly restored, preserving as much of the original soul as possible, it promises to be a luxury stay in understated sophistication with 100% linen sheets, beautiful kitchen/dining, lovely private outdoor space, tranquil idyllic work/recharge areas, and enough space to make your own history. You won't want to leave.

Charming Downtown Sawyer Home Close to the Dunes

Enjoy this charming home in the heart of downtown Sawyer. Venture out on foot, and you're a 2 min walk to Greenbush, Infusco, Section House and more. Hop in the car and be at Warren Dunes or Journeyman Distillery in under 10 mins. Centrally located to be close to everything Harbor Country has to offer. Inside you'll find all the comforts of home, including a full kitchen, plush queen beds, as well as a 55" Smart TV with many apps ready to go on the Apple TV. Kitchen & bathroom basics provided.

House of Zen: Peaceful Modern Cabin on Tryon Farm

The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, and close to Indiana Dunes National Park, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum stay during summer, but open up 2 night stays 1-2 weeks before if possible.

Casa Gitana - Boutique Style Stay in Three Oaks

Casa Gitana is a Boutique style stay in the quaint town of Three Oaks, MI. Just a short drive to the pristine beaches of Lake Michigan and walking distance to downtown, our home offers an eclectic & contemporary feel that is perfect for a relaxing getaway any time of the year. We personally manage & oversee the home before every stay, & take pride in putting thought & intention into every detail. We want our guests to feel at home, and most importantly enjoy a comfortable and relaxing stay. :)

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours

Welcome to "Lake 2 Grapes" Bridgman is a little gem located between St. Joe and Warren Dunes. Minutes to Lake Mi. beaches, craft breweries, and wine trails. Relax in the upper level of our bi-level vacation home w/private entrance. This 3 bedroom, 2 bath includes a beautiful Master suite! Enjoy the Hot tub and fire pit in the backyard. Wine Tour? Stay with us and you'll receive a discount with "Grape & Grain Tours" plus complimentary pick up and drop off. Must be 25 or older to book.

The treehouse at Warren Dunes

Looking for the perfect Harbor Country getaway? We've got you covered! Just 90 miles from Chicago and adjacent to Warren Dunes State Park, this beautifully remodeled home hidden in the trees is the perfect escape. With accommodations up to 6 on four levels of living space, you'll enjoy an indoor/outdoor living experience like no other. Conveniently just 200 yards from the beach with walking path access at the end of the street and easy access to all the activities this area has to offer.

Cozy Sawyer Beach Cottage walk to Warren Dunes

Beautiful renovated beach cottage on a quiet tree-lined street. Private comfortable home perfect for a winter weekend away! Enjoy the best of Pure Michigan, 2 mi from Sawyer & 0.5 mi to Warren Dunes State Park. Plenty of outdoor space to play, skylights to soak up the natural light and central to wineries, restaurants and the Dunes. Grab local farm fresh produce, s’mores for the firepit and a local natural wine to sip as you watch the sun set from the huge back deck and large backyard.

Cheerful 3BR 2BA Country Cottage Near Attractions

Your family will be close to everything when you stay at this centrally-located place. We have sought to equip our home to a high standard and to anticipate your needs by providing all the things you might want for a relaxing stay. There are games in the back yard that will interest all ages. Close to beaches, wineries, Four Winds Casino, cross country ski, South Bend football, South Haven and many other locations. We also provide a pass to Silver Beach and all other county parks.

Idyllic A-frame in Michigan’s Harbor Wine Country

Follow a wooded path to a secluded mid-century modern cottage constructed of stone and wood reclaimed wood from a historic St Joe's rollercoaster. Retro pink ceramic tiles line an open-plan main floor surrounded by sliding doors. You will be surrounded by the great outdoors while sitting cozy inside by our electric fireplace. Located about 10 minutes south of downtown St. Joe, our Idyllic A-frame is a perfect location for the escape to SW Michigan that you've been dreaming about.

The Dacha • Hot Tub, Family-and-Dog-Friendly House

A four-minute walk to town and a quick drive to everything Harbor Country has to offer! "Dacha" is the Ukrainian word for a country house where the whole family gathers. Relax in a hot tub facing the woods, watch your kids play from the deck, enjoy coffee and sunrise on the front porch, have a glass of wine on the screened-in back porch, roast s’mores at the fire pit, read quietly in one of our reading nooks - these are only some of your options when you stay at The Dacha.

Northwind Llama retreat “Chicken coop”

Tucked away on a peaceful working llama retreat—voted the #3 stay in the state of Michigan—this charming efficiency suite offers a cozy retreat surrounded by nature. The thoughtfully designed space features ample seating for relaxing after a day outdoors with a convenient kitchenette. Step outside to not one, but two private gardens. A truly unique and tranquil getaway that blends comfort with award-winning countryside charm.

Rainbows End 🌈 Puryear

Discover the tranquility of a charming cottage nestled on a 20-acre farm, surrounded by nature with walking trails that end up at the South Branch of the Galien River. Unwind on the patio with a cozy fire pit and enjoy all the amenities you'll need for a perfect getaway. Just 10 minutes away from the beautiful shores of Lake Michigan and only 3 miles from Four Winds Casino. Experience the peaceful countryside retreat—book now!