Introduction

Bayfield's lodging ranges from historic inns with their own dining rooms to small guesthouses outside town. We checked nine properties below, all confirmed within Bayfield with verified check-in/check-out times and pet policies — one additional candidate turned out to be in a different town entirely and is excluded for that reason. Check-in clusters around 3:00–4:00 PM and check-out around 10:00–11:00 AM across nearly every property, with pet-friendly options the exception rather than the rule.

The Bayfield Inn

A waterfront hotel with roughly a century of history, housing its own year-round Lakeside Dining Room and a seasonal rooftop bar, The Deck. See our restaurants guide for details on both.

*Check-in:

• 3:00 PM | *Check-out:

• 11:00 AM

*Pet Policy:

• Not allowed in the 21 boutique inn rooms; pets permitted only at the affiliated off-site Isaac Wing House rental ($50 one-time nonrefundable fee/pet). Unauthorized pets incur a $250 minimum cleaning fee.

Good to Know: ~100 years serving Bayfield visitors. Peak rates mid-May–October; cancellation policy tightens in summer (14-day notice, forfeits 50%) vs. winter (48-hour notice).

Old Rittenhouse Inn

A Victorian bed-and-breakfast across two historic homes plus a cottage, with its own upscale dining room, Landmark Restaurant.

*Check-in:

• 3:00 PM–9:00 PM (call ahead if arriving after 8:00 PM) | *Check-out:

• 11:00 AM

*Pet Policy:

• Not allowed; registered service animals only.

*Good to Know:

• 20 rooms across two Victorian homes (built 1890s) plus a private cottage. Full breakfast included. Rates roughly $165–$222+/night, seasonal.

Pier Plaza

A single integrated hotel, restaurant, and lounge complex dating to 1937, with 16 hotel rooms featuring private lake-view balconies, run by the third generation of the Johnson family.

*Check-in:

• 3:00 PM | *Check-out:

• Around 10:00–11:00 AM (individual room listings vary slightly; confirm by phone)

*Pet Policy:

• Pets not allowed in the lodging rooms; pets ARE allowed on the restaurant's Pickled Herring deck — don't conflate the two.

*Good to Know:

• Rooms feature private lake-view balconies, some with gas fireplaces, in-room jacuzzis, or full kitchens. 2-night minimum on weekends May–Oct. See our restaurants guide for Pier Plaza Restaurant and The Pickled Herring Lounge hours.

Greunke's First Street Inn & Dining

A combined 12-room inn and restaurant in an 1863 and an 1880 building, with a 1940s-style diner on-site.

*Check-in/Check-out:

• Not published on the official site or any booking listing found — call ahead to confirm before booking.

*Pet Policy:

• Pets welcome with prior approval — a genuine point of differentiation, since most other Bayfield inns disallow pets outright.

*Good to Know:

• 6 of 12 rooms have private bath; 4 share facilities (no A/C in shared-bath rooms per some reviews). Listed in the Directory of Historic Wisconsin Inns.

Woodside Cottages of Bayfield

Newly built cottages on about 8 wooded acres with jacuzzis, gas fireplaces, and kitchens, with direct access to the Brownstone Trail into downtown — more modern-comfort-in-the-woods than genuinely rustic, despite how it's sometimes described.

*Check-in:

• 4:00 PM | *Check-out:

• 10:00 AM (9:00 AM for groups renting 8+ cottages)

*Pet Policy:

• No pets allowed, no exceptions — violation triggers a $500 cleaning fee and immediate termination with no refund. The strictest pet policy of any Bayfield property checked.

*Good to Know:

• 7 cottage floor plans. Minimum 2-night stay (3 nights for major holiday weekends). No smoking/vaping ($500 fee).

Lake Superior Lodge

Formerly the Winfield Inn, a 30-unit property across three buildings on landscaped grounds, a few blocks from the Madeline Island ferry landing.

*Check-in:

• 3:00 PM | *Check-out:

• 11:00 AM (late check-out available until 1:00 PM for a 20% fee)

*Pet Policy:

• No pets of any kind allowed.

*Good to Know:

• 30 units on 3 acres of Lake Superior frontage. Complimentary continental breakfast. Year-round operation. Note: don't confuse with a similarly named "Chequamegon Lake Superior Lodge" that appears on some booking aggregators.

Bayfield Guest House

A boutique guesthouse, formerly Silvernail Guest House, with five named suites featuring lake views and jacuzzi tubs, a short walk to the ferry and downtown.

*Check-in:

• 4:00 PM | *Check-out:

• 10:00 AM

*Pet Policy:

• Not allowed (stated directly on the property's own amenities page).

*Good to Know:

• 6 individual suites (Huron, Ontario, Michigan, Erie, Superior). Managed via Windseeker Rentals. Walking distance to Madeline Island Ferry.

Harbor's Edge Motel

A 21-room waterfront motel directly across from the Madeline Island Ferry landing, with some rooms offering water views.

*Check-in:

• 3:00 PM–8:00 PM | *Check-out:

• 11:00 AM

*Pet Policy:

• Not allowed; service animals only.

*Good to Know:

• Independently owned and operated for over 50 years. Rates roughly $111–$184/night depending on season.

Island View Lodging

A two-suite guesthouse in a secluded, wooded lakefront setting about a mile north of Bayfield, with a private beach and kayak launch.

*Check-in:

• 3:00 PM | *Check-out:

• 11:00 AM

*Pet Policy:

• Not allowed.

*Good to Know:

• SEASONAL — open May 1 through October 31 only, unlike most other properties on this list which operate year-round. Two suites (Sevona, Fedora), each with private coded entrance and a private balcony facing Lake Superior. Full prepayment required at booking due to high demand.

A Property We Excluded

The Washburn Inn is a real, currently operating waterfront motel — but it's located in Washburn, a separate town roughly 10-12 miles (about 15 minutes) from Bayfield, not in Bayfield itself. It's excluded from this guide for that reason, consistent with how this site treats genuinely out-of-town properties elsewhere.

Practical Tips

• Pet-friendly options are the exception in Bayfield: only Greunke's (case-by-case approval) and The Bayfield Inn's off-site Isaac Wing House annex accept pets among the verified properties — Old Rittenhouse Inn, Woodside Cottages, Lake Superior Lodge, Bayfield Guest House, Harbor's Edge Motel, and Island View Lodging all explicitly bar them.

• Island View Lodging is the one seasonal property on this list (May 1–Oct 31); every other verified property operates year-round.

• Woodside Cottages has the strictest no-pets enforcement of any property checked ($500 fee for violations).

• If you want a hotel with its own notable on-site dining, The Bayfield Inn, Old Rittenhouse Inn, Pier Plaza, and Greunke's all fit that description — see our restaurants guide for what each serves.

• Harbor's Edge Motel and Lake Superior Lodge are both genuinely close to the Madeline Island ferry landing if that's a priority.

• Island View Lodging is the pick if a quieter, more remote stay matters more than downtown proximity, but confirm it's within its May–October season first.

Sources and Verification Notes

Each property's operating status, address, and history were checked against its own official site and cross-checked against Yelp or TripAdvisor. Check-in/check-out times and pet policies were independently verified for all nine properties against official sites and current OTA listings; Pier Plaza's exact checkout time and Greunke's check-in/check-out times could not be confirmed with full confidence and are flagged accordingly. The Washburn Inn's location in a separate town was independently confirmed against multiple distance-calculation sources before being excluded.