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Compare 19 Cottages in Ashland with updated reviews, rates, and availability.

Bayfield Fruit Loop Retreat - Main Cottage
Main Cottage winter views side view looking at two large panoramic windows. String lights. View in winter view snow accumulation possible (Dec, Jan-March) all-wheel-drive or four-wheel-drive vehicle recommended slightly Incline driveway.

Bayfield Fruit Loop Retreat - Main Cottage

10.0 out of 10, Exceptional, (48)
"The best stocked, cleanest, and coziest Vrbo we have ever stayed at!! Keep up the good work!"
Bayfield Fruit Loop Retreat - Main Cottage
Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods
Rock garden cottage winter scene snow accumulation possible December through March. Grill available all year long ( outdoor amenities only available mid May through mid October)

Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods

10.0 out of 10, Exceptional, (31)
"This experience was lovely! It is neat as a pin and everything was intentionally placed for aesthetics and ease of use. This is an absolute gem that felt like a cozy, luxurious and rustic experience. Thank you! "
Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods
This cottage is a 2 bedroom(s), 1 bathrooms, located in Cornucopia, WI.
Welcome to Corny Cottage!

This cottage is a 2 bedroom(s), 1 bathrooms, located in Cornucopia, WI.

10.0 out of 10, Exceptional, (18)
"This property is so wonderful! Very thoughtfully stocked, amenities as advertised, with lots of extra touches! The artwork and decor is warm, earthy and varied. I will stay again! Dec 2024."
This cottage is a 2 bedroom(s), 1 bathrooms, located in Cornucopia, WI.
Madeline Island cottage - steps of Lake Superior. CONTACT OWNER FOR SHORTER STAY
Cottage with beautiful beach just steps away

Madeline Island cottage - steps of Lake Superior. CONTACT OWNER FOR SHORTER STAY

9.8 out of 10, Exceptional, (75)
"The view, the sunset, the accommodations. Wonderful. We all were so comfortable amd pleased. Thank you! "
Madeline Island cottage - steps of Lake Superior. CONTACT OWNER FOR SHORTER STAY
Copper Falls Cottage, Lake Front in Copper Falls State Park
Exterior

Copper Falls Cottage, Lake Front in Copper Falls State Park

9.8 out of 10, Exceptional, (29)
"Wonderful time "
Copper Falls Cottage, Lake Front in Copper Falls State Park
Lupine Landing | Tiny Home on the Big Lake
Welcome to Lupine Landing! Your tiny home on the South Shore

Lupine Landing | Tiny Home on the Big Lake

9.8 out of 10, Exceptional, (18)
"We so enjoyed our stay. Beautiful property, well appointed, cozy home. Host bery communicative. "
Lupine Landing | Tiny Home on the Big Lake
Madeline Island Cottage Overlooking Apostle Islands
Sala Architect designed Lake Superior cottage

Madeline Island Cottage Overlooking Apostle Islands

10.0 out of 10, Exceptional, (66)
"Best cabin on the island for families with kids. Our group of friends and our kids love staying here. "
Madeline Island Cottage Overlooking Apostle Islands
Brookside Cottage
Exterior

Brookside Cottage

10.0 out of 10, Exceptional, (4)
"The cottage was very clean, quiet and comfortable. We enjoyed our stay!"
Brookside Cottage
Mission Springs Resort
Living area

Mission Springs Resort

3.0 star property
9.4 out of 10, Exceptional, (53)
"The place was neat, comfortable, and very cozy. I really enjoyed the fireplace and the short walk to the beautiful view of Ashland at the beach area. "
Mission Springs Resort
Beachside Cottage - on Lake Superior
Exterior

Beachside Cottage - on Lake Superior

10.0 out of 10, Exceptional, (2)
"It's evident that a lot of work went in to this house to make updates. Very clean and had everything we needed. Lovely "private" beach area which chairs and cabana. Quiet neighborhood but easy to find. It got a bit chilly so we made good use of the wood stove. Owner went out of her way to make sure we got a couple of sweaters we accidently left there after checkout. Would recommend if you have a small group [2-4 people]. Being able to bring our 2 golden retrievers was a plus. "
Beachside Cottage - on Lake Superior
The Curry Cottage- Country-Snowmobile trail accessible
Exterior

The Curry Cottage- Country-Snowmobile trail accessible

10.0 out of 10, Exceptional, (13)
"This property was so perfect for our trip. Quiet, cozy, and super cute! Everything was very clean. The beds were super comfy. This little home is perfect for a small family or even a couple of friends. Great lactation for lots of hiking to find waterfalls and visiting Lake Superior. Right between the UP of Michigan and Ashland WI. The check in/out was super easy and the owner was very kind. Would come again/ recommend!!!"
The Curry Cottage- Country-Snowmobile trail accessible
Pet-friendly Iron River Cabin With Fire Pit!
Terrace/patio

Pet-friendly Iron River Cabin With Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (1)
"My kids and I had a wonderful time! Would love to come back again. "
Pet-friendly Iron River Cabin With Fire Pit!
Bayfield Fruit Loop Retreat -2 Cottages
Main cottage back deck feature lounge couch with propane fire pit, 6 person dining table lit by string lights. Wooded views.

Bayfield Fruit Loop Retreat -2 Cottages

9.8 out of 10, Exceptional, (8)
"Beautiful landscaping, amenities, and comfort. Every detail covered including kitchen spices, makeup remover, q tips, bathroom sprays, games, and more. We were very comfortable and the views out of all the windows were amazing. We rented both cabins and though the Rock Cabin Cottage had more sleeping space for our family, the Main Cottage was more luxurious with the deck, furniture, propane fire pit, and patio lights. The only consideration I would recommend someone giving some thought to is...
Bayfield Fruit Loop Retreat -2 Cottages
Upson Ski-in/ski-out, End-unit Cabin w/ Fireplace!
Living area

Upson Ski-in/ski-out, End-unit Cabin w/ Fireplace!

3.0 star property
Upson Ski-in/ski-out, End-unit Cabin w/ Fireplace!
All season cottage with sauna overlooking the private beach on Lake Superior
Exterior

All season cottage with sauna overlooking the private beach on Lake Superior

All season cottage with sauna overlooking the private beach on Lake Superior
Mason Cabin w/ Private Dock on Marengo Lake!
Living area

Mason Cabin w/ Private Dock on Marengo Lake!

3.0 star property
Mason Cabin w/ Private Dock on Marengo Lake!
Charming 3-bedroom cottage with WiFi & AC on beautiful Lake Namakagon in Cable.
Exterior

Charming 3-bedroom cottage with WiFi & AC on beautiful Lake Namakagon in Cable.

Charming 3-bedroom cottage with WiFi & AC on beautiful Lake Namakagon in Cable.
Mission Springs Lake House
Living room

Mission Springs Lake House

3.0 star property
10.0 out of 10, Exceptional, (3)
"Looking to get away to a beautiful place with great service on one of the world’s greatest lakes? The Lake House at Mission Springs Resort near Ashland, Wisconsin on Lake Superior’s Chequamegon Bay is just that. Mission Springs Resort is a small family owned resort consisting of four cabins and The Lake House. There is something for everyone at Mission Springs Resort, a wonderful place that aims to please any vacationer. My wife and I were fortunate enough to stay in The Lake House at Mission...
Mission Springs Lake House
Spider Lake Cabin: Boathouse, Canoe, Deck & Sauna!
Exterior

Spider Lake Cabin: Boathouse, Canoe, Deck & Sauna!

3.0 star property
Spider Lake Cabin: Boathouse, Canoe, Deck & Sauna!
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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Other property types in Ashland

Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails.
Exterior

Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails.

10.0 out of 10, Exceptional, (95)
"Wonderful home and property. Excellent for hiking. "
Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails.
North Apartment with Lake Superior Views
Open concept kitchen/living room with Lake Superior Views (1)

North Apartment with Lake Superior Views

10.0 out of 10, Exceptional, (28)
"Cute, well styled apartment with a view of Lake Superior, and a quick trip to downtown. Would stay again!"
North Apartment with Lake Superior Views
Bayfield- Charming Newly Remodeled Condo, Gateway to Apostles
Sea Caves, Sand Island

Bayfield- Charming Newly Remodeled Condo, Gateway to Apostles

9.6 out of 10, Exceptional, (197)
"We stayed 2 nights. Very off seasons, not much going on. Bery nice clean place. Didnt realize we had to climb stairs as my husband had had foot surgery but we made it work. which was"
Bayfield- Charming Newly Remodeled Condo, Gateway to Apostles
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.

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between and per night. These stays offer a chance to reconnect with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Ashland?
There are 19 cottages in Ashland. No matter if you’re traveling with the family or organizing a weekend retreat with your best buds, Expedia can help you find the right place to get in touch with nature.
Why book your cottage in Ashland with Expedia?
Booking a cottage in Ashland is as easy as deciding on your travel dates and picking your ideal place for outdoor fun and relaxation. From luxurious retreats to budget-friendly properties and cottages that feature conveniences like a kitchen, Expedia has something for all styles. As for epic deals? We’ve got them as well!
How can I find cheap cottages in Ashland?
Expedia can help you locate cheap cottages in Ashland. To reserve the perfect stay in just a few clicks, use our convenient filter tool to refine your search by star rating, budget and amenities.