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Three Oaks Vacation Rentals

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Vacation Rentals in Three Oaks

The Sycamore Cottage - 2 BR & 1.5 Bath - Hot Tub - Steps to Downtown

Three Oaks
10.0 out of 10, Exceptional, (76)
"Hot tub was amazing, great location, walking distance to everything! "
United States
kelsy p.
$283 nightly
The price is $294
Nov 9 - Nov 10
Total with taxes and fees
The Sycamore Cottage - 2 BR & 1.5 Bath - Hot Tub - Steps to Downtown

Ellie`s Cottage with Cherry Beach

Three Oaks
8.4 out of 10, Very Good, (25)
"Very nice house and the outside screened porch is great!"
United States
Nicole P.
Ellie`s Cottage with Cherry Beach

The Neighborhood Hotel - Grand Beach

4.0 star property
New Buffalo
9.6 out of 10, Exceptional, (63)
"Great stay for a large family, stayed in the 3 bedroom suite. "
United States
Mario-Julie
The Neighborhood Hotel - Grand Beach

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Michigan City
9.6 out of 10, Exceptional, (121)
"the house was very spacious and clean. "
United States
Haley G.
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

Michigan City
9.6 out of 10, Exceptional, (242)
"We enjoyed our stay. Everything was picturesque and would definitely recommend staying here."
United States
Carrie H.
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

Sunset Dunes Vacation Villas

3.0 star property
Bridgman
9.6 out of 10, Exceptional, (12)
"This is an attractive, comfortable, well-maintained, and conveniently located rental. We enjoyed our stay and would stay here again."
United States
Blithe
Sunset Dunes Vacation Villas

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Michigan City
9.4 out of 10, Exceptional, (124)
"The location was PERFECT. Just a 5 minute walk down a sandy path to a beautiful beach and Lake Michigan! The tiny cottage was perfect for two people. The bed however is very very hard. If you’re young you’d be okay, but us older folks don’t do well on firm beds lolOther than that our weekend stay was perfect!"
United States
Natasha W.
$248 nightly
The price is $278
Nov 9 - Nov 10
Total with taxes and fees
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

New Buffalo
10.0 out of 10, Exceptional, (79)
"Our stay at Red Oak was wonderful! The house was beautiful! Mary was an excellent host!"
United States
Kelly D.
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Arcade Game Barn

2.0 star property
Sawyer
10.0 out of 10, Exceptional, (28)
"House was perfect for our multi family family vacation! Amenities were wonderful and its clear that Tim is passionate about hosting a wonderful saty for all his guests! "
United States
Kristy D.
Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Arcade Game Barn

Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

Michigan City
9.8 out of 10, Exceptional, (149)
"My family has rented this property for a number of years now and always enjoy our time. Plenty of space and amenities for all. We were blessed with great weather, which always adds to vacation time. We will do it again!"
United States
Mari S.
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

Lakefront! Secluded, HotTub, Fire Pit, Private Dock&boats 90 Min from Chicago

Union Pier
10.0 out of 10, Exceptional, (132)
"Very comfortable, steps to a dock, use of canoe, fishing, hot tub, Firepit for roasting marsh mellows. Very pleasant stay."
United States
Kenneth
Lakefront! Secluded, HotTub, Fire Pit, Private Dock&boats 90 Min from Chicago

Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

New Buffalo
9.2 out of 10, Wonderful, (70)
"Great backyard space to hang out. Awesome location to walk and explore the area and an easy drive to other spots along the lake. The few minor issues we had were quickly communicated and addressed with the owner, so the trip went on without a hitch."
United States
Laura P.
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

Charming & cozy in-town retreat in the heart of New Buffalo

Downtown New Buffalo
10.0 out of 10, Exceptional, (167)
"What a perfect getaway! The house was spotless, super comfy, and in the best location. Our two dogs were in heaven with the fenced yard, and we all loved the dog beach at Warren Dunes just 20 minutes away. So many little touches made our stay extra special. We can’t wait to come back!"
United States
Enid H.
Charming & cozy in-town retreat in the heart of New Buffalo

BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES

Michigan City
9.6 out of 10, Exceptional, (327)
"Hidden treasure! Wish the path to the beach was easier…lugging equipment was a workout! Realized that it costs as much to stay here as it would have on the beach walk (more modern and new). But kids loved the games in the apartment!"
United States
Lenna M.
BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES

The 1888 House-Beach Town Luxury

Benton Harbor
9.2 out of 10, Wonderful, (7)
"Great two bedroom house nearby downtown St Joesph. The only complaints were that there was little to no handsoap, very little paper towels, and no hooks to hang up shower towels. Overall not a bad house, great host."
United States
Sean K.
$311 nightly
The price is $328
Nov 9 - Nov 10
Total with taxes and fees
The 1888 House-Beach Town Luxury

VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!

Michigan City
8.8 out of 10, Excellent, (23)
"Good location great pool host was nice to deal with. Had a good time"
United States
T H.
$464 nightly
The price is $520
Nov 9 - Nov 10
Total with taxes and fees
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!

Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

Michigan City
10.0 out of 10, Exceptional, (203)
"Super host, great amenities and really nice home for 6 adults and 4 children. "
United States
Judith M.
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!

Downtown New Buffalo
10.0 out of 10, Exceptional, (182)
"Great house for our family! It was clean and spacious and very convenient to everything fun in New Buffalo!"
United States
Amelia F.
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!

On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views

Michigan City
9.6 out of 10, Exceptional, (75)
"Fabulous, private, quiet. Two minute walk to beach (literally). Well outfitted kitchen. Favorite spot was the porch! Everything needed for a beach vacation was provided. Throughly and absolutely enjoyed our stay. "
United States
Katie M.
$502 nightly
The price is $510
Nov 9 - Nov 10
Total with taxes and fees
On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views

7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!

Michigan City
9.0 out of 10, Wonderful, (64)
"We were a large group- 5 families. We all fit in the house with plenty of room. Kitchen and eating area work well for big meals. Beach access was perfect. House is a little run down, but all just cosmetic and what I expect from a vacation rental. I would rent again."
United States
Eliza B.
7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Three Oaks Hotel Reviews

Find out more about Three Oaks

Everything you need to know about Three Oaks vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Three Oaks vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Three Oaks vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Three Oaks vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Three Oaks. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Three Oaks in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $278 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Three Oaks rentals

At Expedia, we put the best Three Oaks vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Three Oaks rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Three Oaks vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Three Oaks. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Three Oaks?

Yes, we give you a choice of vacation rentals near the most popular local attractions in Three Oaks, or you can choose a more secluded option if you're looking for relaxation. Three Oaks is known for its waterfront.

What are some of the best vacation rentals in Three Oaks?

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!: This vacation home rental outside of Three Oaks is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Three Oaks?

Choose from 72 Expedia vacation rentals in Three Oaks for a memorable vacation.

What’s there to see and do in Three Oaks?

Enjoy the outdoors at Cherry Beach and Chikaming Township Park and Preserve, or simply take in cultural attractions like The Acorn and Vickers Theatre. Other places in town to visit include Three Oaks Township Hall and Warren Woods State Park.

What’s a vacation rental in Three Oaks like?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Three Oaks. Vacation rentals offer extras such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.