Vacation rentals with a pool in Sawyer, Weesaw Township

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

Epic Indoor Pool w/slide & hot tub close to beach

Escape to Vine Vista, a 3+ acre retreat near Lake Michigan beaches, wine & beer tastings & the third coast. Enjoy a large private indoor heated pool (larger than many hotels!) & hot tub. Accommodates groups of up to 25. You can see why it will be featured in the Emmy Award-winning show Staycation as one of the highlights of the area. Unwind in privacy, but close to local attractions. Dining accommodations for family reunions, birthday celebrations, holidays or bachelor/bachelorette parties.

Las Moras, 6 Acres, and a Large Pool

Come and enjoy Nature at Las Moras (“The Berries” in Spanish) with rows of blueberry bushes, watch the deer prance through the front yard, see the wild turkeys in the woods, watch the turtles in the pond as you enjoy the 25x30 salt water heated pool, surrounded by a beautiful forest and flowering shrubs, in a stunning setting. The renovated cottage is in a secluded 6 acres, surrounded by an open land preserve, all of this is close to Downtown Sawyer and Cherry Beach, 90 minutes from Chicago

Rosie’s Cottage close to Warren Dunes (w pool)

Welcome to Rosie's Cottage! The cottage has three bedrooms with queen beds, two bathrooms, a fully appointed screened in porch, a lovely fenced deck, an outside eating and lounging area, a full additional kitchen, and fire pit (with seating)! During the summer we have a heated pool. (POOL CLOSED FOR SEASON) And don’t forget the kids' playroom, twin daybeds and pull-out couches in the basement for movie nights with the kids. The cottage is walking distance to the beach and Warren Dunes.

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.

New Buffalo / Union Pier Pool Hot tub 6 Bedroom

Relax with the whole family at this peaceful home with Classic European style meets Lake Michigan! This astonishing turnkey home is the perfect escape from life in the busy city. The home is ideal for entertaining Famliy . 5 bed , 4 bath , hot tub and gas grille and( pool opens June 6) close to union pier beaches and wine country . Property is nestled in a quaint country road location 1/2 mile off re arrow highway. Room for 10 cars,blue stone patios,ping pong table .

Designer Cottage Relax Beach Pool & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, pool, 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!

Casa Playa New House in Union Pier w/ Private Spa

This 4 bedroom getaway is located in the heart of Harbor Country and is just a 10 minute walk or 3 minute drive to the best beach in Union Pier! Casa Playa has EVERYTHING a vacation house can offer: an association POOL, a private HOT TUB, high speed internet that accommodates many people working from home, a cozy indoor fireplace, an outdoor fire pit, an outdoor deck & grill, 2 smart Tvs, ALL brand new appliances, and games for the whole family!

Heated Pool | Quiet Area | Huge Fenced Yard

Enjoy a quiet, peaceful neighborhood while being close to everything. Five minute drive to Warren Dunes, Weko beach, wine bars, breweries, and restaurants. Three bedroom ranch perfect for your family to relax and have fun. Large fenced in backyard with gorgeous in-ground heated pool (June-September), gas grill, solo stove. Close to many wineries, orchards, and local farms. Lovely area for bicycling!