Holiday houses in Chequamegon Bay

4.99 out of 5 average rating, 104 reviews

Cabin in Hayward

Seeley Oaks A-Frame | Quiet, 40 Acres, Near Trails

This is a cabin-in-the-woods experience! The Seeley Oaks A-Frame is our slice of the peaceful Northwoods experience. It's on 40 private, tranquil acres (no neighbors!) with great access to all the Hayward-Cable area has to offer. It's small - intended for two adults, with the option of 2 addtl kids. It's a total of 700 sq ft, with a queen bed in the loft, in-floor heat, full kitchen, and washer and dryer. Less than 2 mi from Highway 63, 8 mi from Cable, and 10 mi from Hayward. IG: @Seeleyoaks

4.99 out of 5 average rating, 368 reviews

Guesthouse in Ashland

Norrsken Scandinavian Cottage

The guest cottage is painted to resemble a Scandinavian retreat. Complete with separate bedroom, extra fold-out sofa queen bed, kitchenette, wood burning stove, WiFi (the best we can find but not great!!!) and large television (DirecTV), it is a great getaway for a couple or a family. Owners live on property if you need anything. If you are a bit adventurous, we can put up a tent right next to Lake Superior. The entire property is smoke free. For a quiet stay, no snowmobiles or ATVs.

Shipping container in South Range

4.98 out of 5 average rating, 148 reviews

Sölveig Stay: Shipping Container with Nordic SAUNA

Storage containers converted into a Nordic sauna and living space. Set in the woods half a mile from the sandy south shore of LAKE SUPERIOR. Our two-person occupancy and minimal design are curated to re-focus and re-fresh its inhabitants. Located on 80 acres of private land, you will fall in love with the peace and quiet. Whether you’re looking for a romantic couples getaway, spa weekend, or workspace as a digital nomad, Sölveig Stay was designed to spark creativity and relaxation.

4.86 out of 5 average rating, 111 reviews

Tiny home in Two Harbors

Hillside Tiny Home with Private Sauna

Retreat to our luxury tiny home in the forest with stunning views of Lake Superior! Enjoy the king size bed, heated floors, large kitchen, full bath, and spacious loft w/ queen bed. Private setting includes a panoramic sauna, deck, campfire, grill, and more. Just north of the Split Rock Lighthouse and Gooseberry Falls, you'll never run out of activities during your stay. Bike on the paved trail, or hop on the mountain biking trail or hiking trails. Now booking 9 months in advance.

4.79 out of 5 average rating, 159 reviews

Condo in Bayfield

One Minute Walk to Lake Superior. Brookside #10

Amazing location! This Comfy Studio Condo sleeps 4, King bed & Queen sofa sleeper. kitchen, balcony, AC, CableTV, Strong WiFi, BBQ, fire pit, jet-tub/shower. Walk to the restaurant, bar, marina and pool. The pool opens in July. Brookside is 2.3 miles from Bayfield. Hike or bike the Brownstone trail along the lake. Ride the ferry to Madeline or cruise the Apostles. Sail, fish, kayak, golf, orchards, ski. Mt Ashwabay, Big top , Bayview beach plus many trails within minutes.

4.87 out of 5 average rating, 157 reviews

Home in Ashland

Bungalow (House) on Chequamegon Bay.

This newly renovated fully furnished home is located within one block from beautiful Chequamegon Bay, Ashland's Oredock Pier, walking and bike trail, boat ramp, and beach. Grab a pole and head down to fish off the Ashland Oredock pier, or pack up for picnic at the beach, launch your boat, kayak or canoe. Take a walk, bike, or run on the walking trails. It is short walk to a few local restaurants and the downtown area. Access snowmobile trails. No pets are allowed.

4.9 out of 5 average rating, 116 reviews

Condo in Ashland

Main Street apt 2 blocks from Lake Superior!

STELLA South Shore Stay is a new, gorgeous, one bedroom apartment just two blocks from Lake Superior, located on Main Street in Ashland, WI. Enjoy amenities like memory foam mattresses, high-quality bedding, Wi-Fi, all natural skin care, and much more. Walk to Lake Superior in minutes, get a coffee at the Black Cat or a pastry at the bakery, or enjoy the many restaurants and shops on Main Street. You can also enjoy the many local hikes or check out the Apostle Islands.

4.98 out of 5 average rating, 158 reviews

Chalet in Bayfield

The Acorn of Little Sand Bay Dog Friendly

Modern, rustic, Aframe cabin in the woods with beautiful, simple décor, fully equipped kitchen, new appliances, glass stove top, airfryer oven, filtered H2O/ice maker. Enjoy a luxurious bathroom, heated tile floor, walk-in shower, shampoo/conditioner/bodywash provided. King-size bed in the loft area. Smart TV, wifi. Books, games, bluetooth speaker The woodstove heats the cabin perfectly in the colder months. All wood provided. There is also a minisplit heat/ac unit.

4.94 out of 5 average rating, 435 reviews

Yurt in Bayfield

Twisting Twig Gardens and Orchard Yurt

Our yurt offers a sweet retreat in the woods about 10 miles outside of Bayfield. We are located on a small working organic farm with vegetable gardens, apple trees, and rustic accommodations. We are close to great outdoor recreation near Lake Superior and are about 6 miles from Meyers Beach in the Apostle Islands National Lakeshore. Our property is located on 40 acres and is very remote. We are on the edge of thousands of acres of county land. The perfect escape!

4.95 out of 5 average rating, 349 reviews

Yurt in Bayfield

Bayfield Rustic Yurt 2 (Terra Cotta)

Nestled in the middle of the Bayfield County Forest, this rustic, minimally maintained yurt has direct access to miles of non-motorized rec trails (mountain bike, cross-country ski and hiking). Enjoy panoramic views of Lake Superior including; Pike's Bay, four of the Apostle Islands (Madeline, Basswood, Stockton and Michigan) and the Upper Peninsula of Michigan. Come prepared to relax, unwind and explore the wonders of the north woods.

4.96 out of 5 average rating, 114 reviews

Cabin in Bayfield

Romantic Vineyard Cabin, Sauna, Plunge Pool

Come and celebrate all that Bayfield has to offer at this quiet vineyard and forest getaway, just 2 miles from downtown. Located in Bayfield's charming Fruit Loop, you'll be surrounded by vines, forest, orchards, and berry farms. The Scandinavian cabin, forest facing sauna with plunge pool, and vineyard sit within 5 acres of woods, secluded from roads and neighbors. The cabin has an occupancy limit of 2 adults and one dog.

4.95 out of 5 average rating, 200 reviews

Cabin in Washburn

The Long House

My place is close to Lake Superior and the Apostle Islands It is located 2 miles north of Washburn or 10 miles south of Bayfield. Peaceful country setting, the long house is a freshly remodeled mobile home. Sorry, no pets. I have increased the number of guests to six . There are 4 double beds in the cabin. If you are booking with more than 4 guests, please allow for this. Thanks you! Open June 1 - mid October

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Chequamegon Bay holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Chequamegon Bay

4.76 out of 5 average rating, 21 reviews

Home in Washburn

Up North Oasis | Families & Dogs in Bayfield Area

LisaRating, 5 stars1 week ago

The place is great. Clean, and lots of little touches to make it feel like home. It’s only a few blocks from the main strip with a coffee place, a couple bars and pubs, and a grocery store. We found two beautiful places to hike within 5-12 minutes driving. Perfect location for a home base while exploring the peninsula and kayaking etc.

5 out of 5 average rating, 22 reviews

Home in Ashland

A Cozy Getaway in Ashland

TracyRating, 5 stars1 week ago

This is a great little house within easy driving distance to the many nearby state parks. Very clean, with nice little extras thrown in. Very easy check in and check out. The kitchen was well stocked. Beds were comfortable. Towels were so thick and soft I really wanted to take them all home with me - but I resisted. I will say, if you are someone that likes having a topsheet on your bed - you will need to bring one. Not everyone likes the same night temperature setting and it was either have the top quilt on or nothing. I would happily book again next time I am in N. Wisconsin. Thanks for a great stay!

Home in Washburn

4.74 out of 5 average rating, 361 reviews

The Red Onion House near Bayfield

KellyRating, 5 stars8 months ago

The host was extremely pro-active with communication, gave suggestions for local things to do and the home was comfortable. We overlooked the fact that there is not a television, but there is WiFi so we played a lot of cards and listened to music.

5 out of 5 average rating, 39 reviews

Cabin in Ashland

Relaxing cabin with fireplace on Lake Superior

CassidyRating, 5 stars2 months ago

Cottage 5 was perfect for a cozy and quiet getaway. Very spacious and clean, also had pretty much everything you would need. Plus the ice cream gift, was a great treat! Thank you!!

4.92 out of 5 average rating, 49 reviews

Cabin in Wakefield

Superior Sunset Cabin

MirandaRating, 5 stars2 weeks ago

Absolutely stunning stay. Nestled right on Lake Superior and just minutes from the Porcupine Mountains, this place felt like a hidden gem. No service meant total unplugged peace…just the sound of waves, the breeze through the trees, and endless stars at night. The sunsets were spectacular, the kind that make you stop mid-sentence just to soak it all in. Honestly not sure how they got lucky enough to own such a magical spot, but I’m so grateful they share it. The cabin was cozy, clean, and had everything we needed for a perfect offgrid escape. Would come back in a heartbeat.

Home in Herbster

5 out of 5 average rating, 6 reviews

Timber & Tide Retreat

RobertRating, 5 stars1 week ago

We were very impressed. Host communication was excellent. Checking in and out was a breeze. The place was spotlessly clean. Linens and towels were great. There were nice perks like lap blankets and extra throw pillows. There are multiple separate indoor and outdoor sitting areas, all boasting incredible views of Lake Superior. The photos undersell the proximity to the lake. The outdoor firepit was great, and firewood and kindling were provided. The kitchen is well appointed and we had all we needed to cook meals. We had plenty of space to spread out and relax. The location is quiet. We were never aware of neighbors. We saw deer, red fox, sandhill cranes, wild turkey, and lots of other wildlife nearby. We watched sailboats on the bay. We appreciated the area's local charm, and browsed shops, explored nearby towns, and ate at local restaurants. The whole experience felt like a Norman Rockwell painting at times. We'll be back.

5 out of 5 average rating, 31 reviews

Home in Bayfield

King Beds • Fire Pit • EV • Groups/Family & More

BradleyRating, 5 stars1 day ago

Adam & Casey have done a great job with this house! Very comfortable and luxurious! This was a last minute trip for us and Adam & Casey communicated everything we needed in a very timely matter, and continued to reach out to make sure everything was alright throughout the stay! Highly recommend staying at this house!