House holiday rentals in Gaylord

Retro Retreat right on Main Street Gaylord!

Make some memories at this unique and family-friendly home. This Retro vibe makes you feel like you are visiting Grandmas, especially with all the fun to be had! Not only is it close to all the down town action but it is less than a mile from 500 miles of snowmobile and bike trails spanning 8 counties. Ostego golf club and skiing is less than a mile away. Treetops resort is 7 miles, Boyne mountain and 20 plus golf courses within 30 minutes. Ostego Lake and Burt Lake are all less than 30 minutes!

Value · Family · Getting around

Anni's Cozy Cottage

Welcome to Anni’s Cozy Cottage, a lakeside retreat nestled on beautiful Otsego Lake, Gaylord, MI. This charming getaway is perfect for every season — whether you're looking to fish from the dock, enjoy morning coffee with lake views, or hit the nearby slopes in winter. Step outside and onto the snowmobile/bike trail for year-round adventure. Enjoy boating, swimming, fishing, golf, snowmobiling and skiing. Anni’s Cozy Cottage offers the perfect blend of comfort, convenience, and Up North charm.

Location · Family · Pets

Stunning Cabin - Arcade & Pickleball - sleeps 13

Welcome to Porcupine Lodge, relax with the family or enjoy some time away with your friends! Located 1 mile into Michaywé golf community and 12 minutes from Downtown Gaylord, our cottage provides ample privacy with empty lots on both sides, but easy access to 17 golf courses, 2 ski resorts, miles of snow mobile trails, along with dozens of bars and restaurants. Enjoy the multiple entertaining areas, brand new kitchen, natural gas grill and the Michaywé indoor/outdoor pools, hot tub and sauna.

Family · Value · Air conditioning

The A-Frame at Finch Creek - Secluded w/ Hot Tub

Welcome to the A-frame at Finch Creek. A one-of-a-kind Northern Michigan getaway overlooking Finch Creek and completely surrounded by the Grass River Natural Area. We renovated this 1970s cabin from the ground up and designed it to feel open and connected to the landscape. With 20-foot vaulted ceilings, massive picture windows, a fireplace to curl up next to, and just minutes from some of the most stunning lakes in the state, it’s the perfect home base for exploring or doing nothing at all.

Location · Value · Skiing

Beautiful Sonshine Corner

Escape to serenity in this rental home located in the countryside less than two miles from Treetops and Otsego Resort, both offering premier skiing and golf. It is also walking distance from Sonshine Barn Wedding & Event Center, and has a three-mile access to shopping and restaurants. Includes: - Grill - Horse shoes - Ping pong table - Pool table - Fully stocked kitchen - Washer & dryer - Attached garage - Heat & A/C - Back deck with furniture - Bonfire pit with chairs and wood provided

Family · Location · Hospitality

Keene Acres

Come enjoy this peaceful piece of country nestled in Maple Forest Township. Centrally located between Grayling, Gaylord, Traverse City and Alpena. Plenty of lakes, rivers, and ORV in the area.Plenty of room for family and pets to explore the great outdoors. All season paradise. Close to snowmobile, ORV, cross country ski trails. Great inland lakes and fly fishing in Au Sable and Manistee Rivers. Kayak and canoe liveries nearby. Surrounded by 700 acres State Land. Located 2 mi. off I75.

Family · Location · Kitchen

The Main House

Welcome to The Main House. Location is everything when it comes to getting around Northern Michigan. Centrally located in Gaylord, quick access to local golf/ski resorts, short drive to many up north tourist activities, and even perfectly located in our Alpine Village. Walk to downtown and enjoy Gaylord's night life. Tastefully updated 5 bedroom home perfect for large groups and families. Enjoy our outdoor spaces as well, fenced back yard, large porches and beautiful flowers.

Value · Location · Sleep quality

Golf | A-Frame | Hot Tub | Sauna | 2 King Beds

Sunshine Chalet Gaylord is a Charming A-Frame ski haus featuring treehouse views. Just minutes from Otsego Resort, Treetops Resort, and a short drive to Boyne Mountain, this is the perfect location for winter enthusiasts or golf retreats. Charming downtown Gaylord's restaurants, pubs, and shopping is just around the corner. Experience a true up-north stay with valley views, and; *Hot Tub *Sauna *Double Decks *Fire Pit *Fire Table *Gas Grill & Charcoal Grill *Coffee Bar *Hammock

Location · Family · Accuracy

Timber Valley Chalet Ask about seasonal discounts

Timber Valley Chalet provides 4 seasons of rest, relaxation and outdoor fun. 3 bd/2ba +basement to sleep 14 . 5G wifi, full kitchen, fireplace, deck, firepit, backyard that opens up to the woods...everything you need. Easy access to all outdoor activities: ski (downhill & x-country), golf, snowmobile, fish, hunt, hike, bike, boat, swim, atv, snowshoe, ice skate...all in Gaylord. Centrally located in the top of the Mitt, we are also an easy drive to much of northern Michigan.

Location · Value · Air conditioning

Up North Living - Outdoor Fun w/Friends and Family

Up North Living is set up perfectly to fit all your family & friends under one roof to have fun, relax, enjoy the fresh air and most importantly make memories! The colorful Fall & sparkly winter are great for tearing up the ATV & snowmobile trails, skiing/sledding at Treetops or just hanging at the house with some boardgames! Summers here are full of adventure with a quick drive to Mackinac, Traverse City, or Michigan’s north coast beaches. Must be 21 or older to book!

Location · Family · Getting around

Secluded Hot Tub Hide-A-Way Retreat

Kick back and relax in this calm, stylish space. Very secluded on 6 private Acres. Relax around a camp fire in the evening or listen to the birds in the morning (you can often hear the loons early in the morning). This was built new in spring of 2025 and ready for your up north experience. Just 3 miles from Bellaire, 6 miles from Schuss Mountain for golf and skiing. 45 minutes from Traverse City and Petoskey. The perfect launching point for all NW Michigan has to offer.

Value · Location · Check-in

Kassuba Lake Retreat

Escape to Kassuba Lake Retreat, a four-season lakefront vacation rental in Gaylord, Michigan, just minutes from Treetops and Otsego Resort. This peaceful 2-bedroom home sleeps 6 and features private lake access, a dock, kayaks, fishing, a fully stocked kitchen, WiFi and beautiful Kassuba Lake views. Perfect for golf trips, ski and snowmobile weekends, summer lake vacations, or a relaxing Northern Michigan getaway.

Value · Family · Accuracy