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Happy Days and Nights - Bear's Den

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Room
Room
Bathroom
Property grounds
Terrace/patio

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Gym
$225
avg per night

Explore the area

View in a map
Harbor Springs, MI
  • Place, Pleasantview Winery
    ‪1 min walk‬
  • Place, Happy Days and Nights Winery
    ‪2 min walk‬
  • Place, Nub's Nob Ski Area
    ‪13 min walk‬
  • Airport, Pellston, MI (PLN-Pellston Regional)
    ‪27 min drive‬

Rooms & beds

1 bedroom (sleeps 2)

Bear's Den

1 Queen Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Price is $225 avg per night

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About the neighborhood

Harbor Springs

Harbor Springs is home to this bed & breakfast. Pleasantview Winery and Happy Days and Nights Winery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Lake Michigan and Petoskey State Park. Great Lakes Center for the Arts and Cheboiganing Preserve are also worth visiting. Be sure to check out the area's animals with activities such as game walks and birdwatching.
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What's nearby

  • Pleasantview Winery - 1 min walk - 0.0 km
  • Happy Days and Nights Winery - 2 min walk - 0.2 km
  • Nub's Nob Ski Area - 13 min walk - 1.1 km
  • The Highlands - 6 min drive - 4.0 km
  • Tunnel of Trees - 10 min drive - 12.8 km

Getting around

  • Pellston, MI (PLN-Pellston Regional) - 27 min drive

Restaurants

  • ‪Piper's Mighty Good Pizza - ‬4 min drive
  • ‪McDonald's - ‬9 min drive
  • ‪Taco Bell/KFC - ‬9 min drive
  • ‪Petoskey Brewing - ‬8 min drive
  • ‪China Buffet King - ‬9 min drive

About this property

Happy Days and Nights - Bear's Den

Happy Days & Nights is a truly unique hideaway near Harbor Springs, Mi. Surrounded by spruce, hemlock, white birch, poplar, and oak trees, this hidden gem offers the ultimate in privacy, tranquility, and wow factor!

Happy Days and Nights is a beautiful, hilltop bed and breakfast with winery that includes a fully equipped tasting room containing hundreds of bottles of artisanal wine, hand-crafted on the premises.

The Bear’s Den is a rustic, woodland themed room with a queen bed and a private bathroom with walk-in shower. It’s located in the wine tasting room building with a private entrance.

There’s a petrified wood basin sink, a walk-in glass shower with pebbled tiling in the silhouette of a waterfall. There’s a flat screen tv, a personal fan, heater, mini fridge, and coffee maker. Guests enjoy clean towels and hand cloths, a hair dryer, and free toiletries. There is breakfast included every morning and a buffet bar in the Sunset House with coffee, water, dry cereal, fresh fruit, and nutritional health samples for guests to enjoy.
Our prices include all fees. No hidden fees.

House Rules

Check in after 3:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
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Children

Children allowed: ages 3-17
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Events

Events allowed: family gatherings, birthday parties, weddings
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Pets

Pets allowed: dogs and cats (limit 2 total)
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Smoking

Smoking is not permitted
Quiet time is between 10pm and 7am. Please take off shoes before going upstairs in the Sunset House. Pets are welcomed. Pet fee is $20. No Grills.
We serve cooked to order breakfast. Menus are given at check in and need to be turned in by 8pm the night before breakfast, except for late check ins.
Add a romance pkg for $75. Includes a bottle of wine, 2 glasses, fake rose petals on the bed, flowers, and Kilwin's chocolates. Give 72hrs adv notice.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Cashless transactions are available
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 19
Safety features at this property include a fire extinguisher, a smoke detector, and a first aid kit

Frequently asked questions

Is Happy Days and Nights - Bear's Den pet-friendly?

Yes, Happy Days and Nights - Bear's Den allows cats and dogs (limit 2 total). Some restrictions may apply, so please contact the property for more details.

How much does it cost to stay at Happy Days and Nights - Bear's Den?

As of Mar 29, 2026, prices found for a 1-night stay for 2 adults at Happy Days and Nights - Bear's Den on May 8, 2026 start from $225, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

What time is check-in at Happy Days and Nights - Bear's Den?

Check-in begins at 3:00 PM.

What time is check-out at Happy Days and Nights - Bear's Den?

Check-out is at 11:00 AM.

Where is Happy Days and Nights - Bear's Den located?

Situated in Harbor Springs, this bed & breakfast is steps from Pleasantview Winery and 2.9 mi (4.6 km) from Lake Michigan. Happy Days and Nights Winery and Nub's Nob Ski Area are also within 1 mi (2 km).

Happy Days and Nights - Bear's Den Reviews

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 42 out of 45 reviews
Rating 8 - Good. 2 out of 45 reviews
Rating 6 - Okay. 0 out of 45 reviews
Rating 4 - Poor. 1 out of 45 reviews
Rating 2 - Terrible. 0 out of 45 reviews

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Eric N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property, wonderful innkeepers, excellent amenities, highly recommended!
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Kris M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great ski weekend

Very comfortable and relaxing stay. The breakfast was great too. We enjoyed the cabin and the sauna which is right outside the door. Perfect weekend away
Stayed 2 nights in Jan 2025
Verified

10/10 Excellent

Anthony V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Happy Days and Nights BnB

Great property with a clean room and delicious breakfast provided.
Stayed 1 night in Aug 2023
Verified

10/10 Excellent

Kelsey H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another great stay

We’ve been coming for a few years in a row to stay when we’re skiing nearby. It’s a great location, warm and cozy and has a great breakfast!
Stayed 3 nights in Jan 2024
Verified

10/10 Excellent

Margaret B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful hosts!

A great location and wonderful, clean accommodations. The breakfasts were so tasty and the property managers so friendly and helpful. We loved it!
Stayed 2 nights in Aug 2024
Verified

10/10 Excellent

Gary

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Chris and Jessica were great hosts. Great breakfasts and hospitality!
Stayed 3 nights in Jul 2022
Verified

10/10 Excellent

Ericka K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Color tour

We had a great time nice little Gem! Would stay again.
Stayed 1 night in Oct 2023
Verified

10/10 Excellent

Alicia P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Michigan Getaway

We loved our weekend in Northern Michigan. Thank you so much for a warm welcome, wonderful room and delicious breakfast’s.
Stayed 2 nights in Apr 2023
Verified

10/10 Excellent

Alana P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Happy at Happy days

Great for a long weekend get away. Conveniently located, very clean and comfortable, with friendly and helpful hosts. Will come back for sure!!!!!
Stayed 2 nights in Jul 2024
Verified

10/10 Excellent

Timothy K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Hidden Gem

Wonderful stay. We didn’t get to have breakfast though. Conveniently located. Undisturbed relaxation.
Stayed 3 nights in Aug 2024
Verified

10/10 Excellent

Steve S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Happy Days

Bears Den was clean and comfortable, but could use a chair. Private setting, and our hosts were helpful and available as needed. Served a great breakfast as well. Would go back again.
Stayed 3 nights in Aug 2023
Verified

10/10 Excellent

Michael H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Happy days and nights indeed!

Loved the Bears den room! And the breakfast was awesome! Thank you so much Chris and Jessica!!
Stayed 3 nights in Mar 2021
Verified

4/10 Poor

Gage P.

Liked: Cleanliness, location, listing accuracy
Disliked: Check-in, communication
When we arrived, it was later in the evening. We were excited to be up north and meeting friends, and admittedly we were in a hurry. The breakfast sign-up policy was explained, and unfortunately we forgot to turn in the breakfast form by the 8 p.m. deadline. I texted the host to apologize and explained that my husband and I are not picky eaters at all and would be happy with anything — we just asked if he could surprise us with breakfast at our already scheduled 9 a.m. time. We were told instead that we would need to be back by 11 p.m., which didn’t work since we were spending our first night visiting with friends. As a result, breakfast wasn’t an option for us. Given the price of the stay, this felt unnecessarily rigid and disappointing.Another major issue was the temperature of our room. It was extremely cold — around 63 degrees for most of our stay. The floors were freezing, and we relied on a space heater just to be comfortable. That was a big drawback and not what we expected.On Saturday, my husband and I planned to relax and enjoy the property. The hot tub itself was very clean, and I was impressed by that. However, the experience was overshadowed by the presence of a Ring camera positioned very close above us. It made us feel like we couldn’t have a private conversation. At one point, the host spoke to us over an intercom, which confirmed we were being monitored. Very unsettling in an area that should be private.
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

KENNETH D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Harbor Springs Stay!

This was my wife and mine first stay at a Bed & Breakfast ever and we loved it. We did skiing lessons at Nub’s Nob and this was the perfect location right down the street. Also a close drive into downtown Harbor Springs. The breakfast every morning was phenomenal and the hosts really went above and beyond with everything. The property is really cool with a lot of amenities, and we really loved the log-cabin style of the Bear’s Den. This was by far our favorite Vrbo stay yet!!
Stayed 3 nights in Jan 2023
Verified

8/10 Good

Susan I.

Liked: Cleanliness, check-in, communication, listing accuracy

Sister Bear Den Stay

Chris and Jessica were very accommodating. Bear Den was perfection. Hospitality by hosts excellent. Property owner needs repair and work on the exterior and grounds were a disappointment.
Stayed 2 nights in Aug 2024
Verified

10/10 Excellent

Carrie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quick Color Tour

My husband and I were traveling to see the Amazing color this fall season and celebrating our 25th anniversary!! Chris & Jess of Happy Days & Nights greeted us upon arrival, showed us around the property and then to our room. This was our first time at a B&B…The Bears Den (1st floor, behind winery) was a Super cute set up! Clean~Cozy~Quiet. We also, enjoyed the hot tub~sauna. Breakfast & Wine Tasting was delish!
Stayed 1 night in Oct 2023
Verified

10/10 Excellent

T G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Private space and friendly hosts

First time using VRBO, and it was extremely pleasant. Ended up being the only ones there that night, and Chris made the effort to do some wine tasting for us. After that, we got to enjoy the hot tub all alone. The room was private, and quite cozy. The bed and pillows were so comfortable that I didn't want to get up. We will definitely contact them in the future if we venture that way again. Chris and Jessica were very kind hosts, and I feel went above and beyond what was necessary. Highly recommend.
Stayed 1 night in Jun 2024
Verified

10/10 Excellent

Catherine P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quaint Mountain Cottage

This property was perfect for my partner and I. We were doing a ski vacation for two days for NYE weekend. It’s right between Petosky and Harbor Springs 5 min from Nubs Nob and The Highlands ski resorts. We skied each day and then went to nice dinners in downtown Petosky and Harbor Springs. Highly recommend the moonlight dinner at the top of the highlands mountain for a romantic evening. The breakfast worked out perfect because we were able to eat in the property and head straight to the slopes. After a long day of skiing it was great to relax in the hot tub and sauna. Everything was clean and the staff was so friendly and welcoming. Highly recommend this for couples looking for a romantic getaway.
Stayed 3 nights in Dec 2022
Verified

10/10 Excellent

Kimberly F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Breakfast and Amenities

We stayed 2 nights at the Bear's Den at Happy Days and Nights Bed and Breakfast. The innkeepers, Chris and Jessica do an outstanding job of creating a welcoming environment. We chose this property because they are pet friendly, but it exceeded our expectations. The Bear's Den is very private as the entrance is on the back side of the wine tasting room. Wine tasting closes at 6 p.m. so it is very quiet in the evenings. There is a beautiful hot tub and sauna for guest use. However, what made the stay was the fantastic breakfast that Jessica and Chris prepare and serve. It is cooked to order and served in a beautiful dining area. We highly recommend this property and will stay again when we visit the area.
Stayed 2 nights in Jul 2023
Verified

10/10 Excellent

Jennifer V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quant get away spot

Chris and Jessica were more like family than hosts. Our breakfast was delicious especially the potatoes. We stayed in the Bear’s Den, which was perfect for us as we brought our 11 year dog. We didn’t take advantage of the wine tasting, but I am sure we will be coming back so we can stay longer.
Stayed 1 night in Oct 2022
Verified

10/10 Excellent

Joleana S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved it ❤️

The place is beautiful. The pictures don't do it justice. We stayed in the Bears den and it was absolutely gorgeous.
Stayed 1 night in Sep 2022
Verified

10/10 Excellent

Margaret A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent location, beautiful property and great wine tasting!

We loved our stay. The room was even nicer than the pictures. The hosts were outstanding! We had a wonderful breakfast and enjoyed wine tasting. I highly recommend Happy Days and Nights.
Stayed 1 night in Sep 2022
Verified

10/10 Excellent

Candace T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Short stay

We had a short one night stay and absolutely loved our experience. The room was cleanly and spacious. Breakfast the next morning was also delicious. The innkeepers were extremely friendly and did a great job. We would definitely stay here again.
Stayed 1 night in Aug 2022
Verified

10/10 Excellent

Julie B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

great location and super nice hosts … thanks for packing my breakfast … so appreciated it
Stayed 2 nights in Aug 2022
Verified

10/10 Excellent

Cathy J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect!

The setting of the property is beautiful and it’s close to Petoskey. Our room (bear / cabin themed) was really nice. And the breakfast was delicious ! Everything about our stay was great ! We will be back 😊
Stayed 1 night in Jul 2022