Vacation rentals with a pool in New Buffalo

Designer Cottage - walking distance to downtown

Dream cottage getaway just over an hour from downtown Chicago. Walking distance from the beach, restaurants and all of downtown New Buffalo. Close to the casino, wineries and breweries. Whether driving in or taking the train, The Bradford is a relaxing yet sophisticated getaway. Eat, drink, and enjoy the beach, the pool, the shops and incredible summer sunsets, all within walking distance! Please note pool/bathhouse open late May - September and is shared with our association.Permit C22-0051

Experience Fall Beauty & Harbor Country Charm!

Important notes: - Home is in HARBERT by the lakefront, NOT in Three Oaks - Hot tub open all year - Pool closes October 10, 2024 through Memorial Day 2025 After a day of exploring the waters of Lake Michigan, Warren Dunes, or nearby wineries, find your sanctuary at Mae's Place. Recharge by soaking in the inviting hot tub, sizzle up a delicious meal on the grill or in the kitchen and end the evening roasting marshmallows around the fire pit or watching an outdoor movie on the pool deck.

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Beautiful home in the heart of Beachwalk, across the street from Lake Kai, pools, basketball & tennis courts and 2 blocks to Lake Michigan. This home is bursting with charm. Front porch runs the width of the house. Dining area opens up to family room with a lovely fireplace. Stunning master bedroom w/walk-in closet and beautiful new bathroom with all the finishes. 3 more bedrooms upstairs, one with full bathroom attached and the other 2 sharing bathroom. 5th bedroom on the lower level.

Modern 5-Bedroom New Buffalo Lakeside Escape

Escape to this stylish and spacious 5-bedroom house in New Buffalo, ideal for large families or groups. This home is perfectly located just a short stroll (3 blocks) from the vibrant shops and restaurants of downtown New Buffalo and within easy walking distance (6 blocks) of the beautiful beach. Enjoy the quiet of a serene dead-end street in a charming neighborhood, relaxing on the covered front porch or enclosed back porch. Guests have access to the pool within the neighborhood.

'Pool Barn Camper' w/Hot Tub near Indiana Dunes

Hot tub open all year! Pool will reopen May 1. Fully equipped RV sleeps 5, has bathroom w/shower, stove, microwave, TV, heat & A/C, & running water all year. Located on the bike trail & only minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hike in the Indiana Dunes National Park along the Little Calumet River & the historic Bailley homestead, only 1 block from the RV. Enjoy our large pool, hot tub, grill, campfire, & playground too. Schedule your visit today!

Cozy 1BR/1BA Retreat w/ Pool Access + Near Beach

This airy space holds warmth in the details — wooden accents, walls the color of pine and sage, the faint smell of a campfire. One king bed features a cushy Casper mattress topped with plush Sferra linens. The bathroom, complete with Malin+Goetz bath products, keep things fresh. A small but mighty kitchenette is home to your morning coffee thanks to a Moccamaster coffee machine, fridge + microwave. If you must remain connected to the real world, the WiFi and TV are solid.

Designer Cottage Relax Pool Beach & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, community pool, private hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax and unwind in this luxurious updated getaway with plenty of sun filled space for all to enjoy year-round. Professional Wolf stove for the chefs. Book your stay today! Create lasting memories!

NEW! 1BR Cottage w/ Pool, Firepit, Walk to Beach

Presenting Townie 1 - The Ivy, part of the unique Townie Cottages collection. This newly built lakeside luxury home was designed exclusively by Kate Marker Interiors (recognized by Architectural Digest and Luxe Home). Located in Union Pier, these exquisite cottages blend rustic charm and modern elegance for an unforgettable stay. Immerse yourself in a meticulously curated interior with high-end finishes and chic furnishings, creating a sophisticated yet homey atmosphere.

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

Autumn at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. Equal parts sanctuary and playground, this designer-owned haven offers both deep seclusion + an open-format layout that invites connection, healing + memory-making. Whether you’re gathering with family, reuniting with old friends, or seeking a rejuvenating escape, we deliver an experience that’s as comfortable + stylish as it is energetically charged.

Couples getaway with hot tub!

Come for a relaxing getaway in the country. Cook in our small kitchenette or use our Blackstone or fire pit. Located in a small hobby farm setting with sheep roaming the pasture. We also have a couple cats that claim the pool area as their own. The long driveway and gravel road are perfect for a leisurely stroll to enjoy the great outdoors. Take a swim in the pool or a soak in the hot tub and let the worries of life melt away during your stay.

Sauna | Hot Tub | Heated Pool | Beach Walk

Welcome to Little Arches, a 5,000-sq-ft Fisher 3 luxury retreat in Grand Beach. 6 beds | 4.5 baths | sleeps 12. Walk 5 min to Lake Michigan or unwind in the sauna, 8-person hot tub, or heated pool (May–Oct, add’l fee). Inside: chef’s kitchen, 3-season room, game lounge, and theater-style basement. Private wooded lot near golf, pickleball, and beaches — the perfect blend of relaxation, recreation, and year-round Fisher 3 luxury.

New buffalo Farmstead main home pool hot tub

5 bedroom 2 bath 2200 sq ft modern farmstead , 2 minutes to new buffalo and beach and all its offerings , 18x36 new heated shared pool and hot tub. Property on 6 acres with plenty of room for kids to play , 26 apple trees and woods , ride host bikes to new buffalo .. Best of both worlds in country , close to town .There’s 2 new homes on 6 acre property, this home and 1 guest home ( rented separately) .