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Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL

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A balcony with wicker chairs and a table, overlooking a scenic landscape.
A spacious loft with high ceilings, large windows, a dining area, and a cozy seating area.
A spacious dining area with a large wooden table and chairs, large windows offering views of greenery, and a chandelier hanging from the ceiling.
A modern two-story house with a stone staircase leading to the entrance, a covered patio with outdoor furniture, and a large window overlooking the yard.
Fridge, microwave, oven, stovetop

Reviews

10 out of 10
Exceptional

Entire home

6 bedrooms4 bathroomsSleeps 12

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Explore the area

View in a map
Elizabeth, IL

Room options

About the neighborhood

Elizabeth

Located 3 mi (4.8 km) from Apple River Fort, this vacation home is within a 15-minute drive of Rocky Waters Vineyard and Winery. The vacation home includes a kitchen, a fireplace, and a balcony.
View more Vacation Homes in ElizabethOpens in a new window

Getting around

  • Dubuque, IA (DBQ-Dubuque Regional) - 51 min drive

Restaurants

  • ‪Bootlegger Saloon - ‬15 min drive
  • ‪Cajun Jack’s - ‬7 min drive
  • ‪E Town Coffee - ‬5 min drive
  • ‪Dually's - ‬5 min drive
  • ‪Eager Beaver Bbq - ‬7 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL

Cliffside Cottage, a secluded wooded retreat located on 50 acres with breathtaking views, a pond to swim, fish, wooded trails, and so much more! A perfect destination to get away from it all while being in close vicinity to so many amenities. The cottage, conveniently located just off Highway 20. Only a 15 minute drive from Eagle Ridge/Galena Territory, and only 20 minutes from Chestnut mountain and historic downtown Galena that offers museums, boutiques & restaurants!

The space
Welcome to your perfect vacation home! 20 minutes from Chestnut Ski Resort, 20 minutes from downtown Galena, and 15 minutes from Eagle Ridge/Galena Territory. Enjoy the privacy this home will offer you as it sits in the middle of 50 beautiful acres.

As you drive down the lane to our cliffside cottage you will instantly feel that you are leaving your busy, hectic daily life and you have entered a place of serene, calming essence and stunning scenery.

The perfect weekend getaway or week-long vacation destination 20 minutes from downtown Galena. As you enter this 6 bedroom cliffside cottage you will instantly feel the privacy with views from every room you enter of endless tree lines, fields, and wildlife. This cottage sits in the middle of the trees on a private 50 acres overlooking one of the most idyllic valleys of Jo Daviess County. Bright and open floor plan with a fully equipped gourmet kitchen that includes an over-sized island providing the perfect area to gather with your group. A screened in porch immediately off of the dining area offers an ideal location to enjoy the outdoors, without leaving the home.

Indoor – The main floor features high vaulted ceilings, fireplace, a breathtaking view from kitchen and living room. A master king bedroom with a full bath. A half bath, and a queen bedroom. Laundry is located right outside the master bedroom for guest use.

Top level bedrooms share a jack/jill style bathroom with a tub/shower. One queen bedroom and one king bedroom. The king room has a balcony to enjoy a glass of wine and watch the sunset, offering plenty of seating for others in your group to join you.

The lower level offers a large living area with a large sectional sofa perfect for movies in the evening or on rainy days. The lower level also offers easy access to the lower level patio. The lower level also includes two bedrooms. There is also a queen bedroom and bedroom with two twin beds and a full bathroom.

Outside you can take advantage of the beautiful scenery on our large screened-in deck, or grill out on the back patio. Enjoy a fire at night with our solo stove. There is plenty of yard and parking space. The cottage is situated on 50 acres with trails and a newly built 2 acre pond to swim and fish in the summer and ice fish and ice skate in the winter. (still filling but will be ready to swim by summer of 2023)

Pool*** - There is no option for pond as an amenity but at our newly rebuilt clear and clean pond you will find yourself kayaking, swimming at the sandy beach, relaxing and making memories with family and friends!! See photos or inquire for more information

We do have property maintenance and security personnel. You may see them around the property during your stay

Our pond is semi-private and shared between our two rental homes, Cliffside Cottage and Cedar Cove Cabin. Guests of Cliffside Cottage have access to the beach area with the dock, while Cedar Cove Cabin has its own private beach area. The pond is enjoyed by all guests for swimming, kayaking, and fishing. We kindly ask all guests to respect each other's space and enjoy their time on the property responsibly. Thank you!
The vacation home is air-conditioned and features a kitchen, 3.5 bathrooms, and a balcony, and there's space to spread out with 6 bedrooms. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a washing machine, a fireplace, and a coffee maker.

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Property amenities

Beach

  • Beach nearby

Ski

  • Cross-country skiing nearby
  • Snowboarding nearby

Pool/Spa

  • Hot tub
  • Outdoor pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 6 bedrooms
  • Bedsheets provided

Bathroom

  • 3.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • DVD player
  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Phone

Location highlights

  • In a rural location
  • Near a hospital

Things to do

  • Snow sports gear
  • Birdwatching nearby
  • Casino nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Ice skating nearby
  • Sledding nearby
  • Swimming nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Deadbolt lock

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • This property welcomes pets
  • Dogs only
  • 1 total pets
  • Service animals exempt from fees
  • Note from host: Must communicate with host before bringing pet

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a smoke detector, and a deadbolt lock.

Frequently asked questions

What is there to do around this vacation home?

This vacation home is located in Elizabeth, close to Massbach Ridge Winery, Apple River Fort, and Rocky Waters Vineyard and Winery.

Is parking available on site at Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL?

No, there isn't parking available at the vacation home.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, this vacation home doesn't have an indoor pool; however, there are an outdoor pool and a hot tub.

Is Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL good for couples?

There are many amenities for couples at this vacation home, including a fireplace, a fireplace in some house, as well as an outdoor pool.

Are there hot tubs at Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL?

No, there isn't a spa tub at this vacation home.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay for free?

Although dogs can't stay for free, they are welcome at this vacation home.

Are there connecting rooms at Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL?

No, this vacation home doesn't feature connecting guestrooms.

Where is the closest airport to this vacation home?

The closest major airport to this vacation home is Dubuque, IA (DBQ-Dubuque Regional), which is about 27.1 mi away.

Are there rooms with balconies that I can book at Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL?

Yes, every house at Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL comes with a balcony.

Cliffside Cottage, Private Pond, 50 acres w/ Breathtaking views near Galena, IL Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 29 out of 29 reviews
Rating 8 - Good. 0 out of 29 reviews
Rating 6 - Okay. 0 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 0 out of 29 reviews

10/10

Cleanliness

Reviews

Verified

10/10 Excellent

joseph B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was awesome! Hot tub was perfect after skiing at the Chestnut Mountain.
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Nick C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house for a weekend friends golf trip!
Stayed 4 nights in Sep 2025
Verified

10/10 Excellent

Rich H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was perfect for our family weekend getaway! Danesa was very welcoming and quick to respond to any questions!Definite FIVE stars!
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Elizabeth M.

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

Wonderful Place to Stay

Lovely, comfortable and spacious, this house was close to so many places we wanted to go.
Stayed 2 nights in Oct 2023
Verified

10/10 Excellent

Kyle W.

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

A great stay!

A really nice property with ample privacy and space. Our family loved it!
Stayed 3 nights in Feb 2024
Verified

10/10 Excellent

Shantyana R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
An absolute GORGEOUS hillside view. The home had everything we needed for a comfortable stay.
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

Courtney F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely beautfiul property! The home was immaculate, well-decorated and cozy. The screened in porch was a favorite of our guests. We loved the big kitchen and all the incredible views.
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Elizabeth K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house was STUNNING!!!! The views were incredible, and there was so much thought put into the decorations.
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Allison S.

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

Perfect for a large group

We absolutely loved our time at Cliffside Cottage! The amount of bedrooms was perfect for us, kitchen was huge and gorgeous. We also enjoyed the outdoor amenities! Would highly recommend!
Stayed 4 nights in Jun 2025
Verified

10/10 Excellent

Matthew S.

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

Great Family Getaway

We were looking for a central spot to celebrate my parent's 50th wedding anniversary...this was a perfect spot with the house and the surrounding land!
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Gina R.

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

Girls Weekend

Beautiful house with awesome views and perfect for our girls weekend away. The drive from Galena to the cottage was so pretty. Would definitely stay again!
Stayed 2 nights in Jun 2023
Verified

10/10 Excellent

Savana R.

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

Amazing place!

Had a wonderful stay and this cliff side cottage. Beautiful views, outstanding house with modern amenities. The host was communicative and quick to respond. Absolutely love this property.
Stayed 2 nights in Sep 2023
Verified

10/10 Excellent

Mark B.

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

Adult siblings weekend

Beautiful house with amazing views. Photos and descriptions all very accurate. Would be very happy to go back again.
Stayed 2 nights in May 2024
Verified

10/10 Excellent

cheri L.

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

ski trip

home was beautiful and well stocked- view was amazing owners were easy to reach and responded quickly to any questions. it was a great weekend
Stayed 2 nights in Feb 2023
Verified

10/10 Excellent

Erik G.

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

Friends weekend

This place has it all. Great views, lots of space, amazing swimming pond to kick back and relax. The host was super friendly and willing to provide as much information as we needed. Perfect getaway spot for families and larger groups looking to get away. argergroups
Stayed 3 nights in Jul 2024
Verified

10/10 Excellent

Tim L.

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

Beautiful Home

This place is beautiful. The views are incredible and everything in the house is well done. Although the pond wasn’t ready, the host was nice enough to let us use their private pond, which was a lot of fun for our young kids.
Stayed 2 nights in Jul 2023
Verified

10/10 Excellent

Charlotte D.

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

Making Memories with Family

I found so much peace here. The view and the sunsets were phenomenal. This home is well appointed and the host accommodated an early checkin for my daughter’s family who traveled here. There was a lot of thought put into the design and construction as it accommodated 3 families comfortably. We skied at Chestnut and shopped in historic Galena, both equidistant from Cliffside Cottage. I highly recommend a stay.
Stayed 2 nights in Jan 2024
Verified

10/10 Excellent

Michael D.

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

Wonderful Stay

Cliffside cottage is a beautiful home with stunning views. The amenities are fantastic - from the smokeless fire pit to the marvelous pond! The kitchen is well stocked with every utensil you’ll need for cooking, the beds are comfortable, and the house is has a great layout for guest to spread out. Danesa was an attentive host who checked in with us just enough and was quick to respond when needed. We’ll be back for sure!
Stayed 5 nights in Aug 2024
Verified

10/10 Excellent

Michael C.

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

Galena stay

Property is beautiful. Location feels really remote. All the amenities functioned properly. I stayed with my mother and my 2 brothers and our 5 total kids. Kids loved the pond! I was able to prepare all the meals with everything on-site. We will definitely look to book again.
Stayed 2 nights in Jul 2023
Verified

10/10 Excellent

Vicki B.

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

Beautiful house and views with privacy

We stayed here for a weekend for our son's wedding at Oak Hill Farm. We had 9 adults who all had their own bedroom with one bedroom to spare. The views were amazing from both top and bottom patio with plenty of outdoor seating and a fire pit. We did not get to use the pond but it was very cute with a dock and small beach. Owners will easy to work with and communicated promptly.
Stayed 3 nights in Aug 2024
Verified

10/10 Excellent

Sharon B.

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

Great secluded spot!

The views from this home are beautiful! Sunsets were gorgeous. House is secluded and we only left once. Hunkered down for thanksgiving weekend with lots of food, cards and football. Well equipped, comfortable home. I’m sure the summer is even better with a private pond. Perfect home for a family get away, or couples getaway with lots of bedroom options. Would definitely stay again.
Stayed 4 nights in Nov 2023
Verified

10/10 Excellent

mike W.

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

Quick trip

We generally rent homes when traveling as an exec team. We chose this property for its proximity to our plant in Stockton,Il. Where we were able to host a small group for dinner. The location was perfect and the house is very nice. We all were amazed by the view and beautiful sunset. Three of us stay d overnight with great no issues. The amenities are nice and the cottage is well equipped. My only thought is that unless your family the bed/bath setup is not adequate for 6 bedrooms. Simply due to sharing bathrooms.
Stayed 2 nights in Mar 2025
Verified

10/10 Excellent

Sharonjit S.

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

Beautiful home and great hosts!

Incredible stay with GORGEOUS VIEWS! The host made you feel as though you are at home. Very responsive and replies to all your questions/needs (before and during trip). We stayed during July 4th, so we were able to see the fireworks as well. All the rooms are clean and beautiful design/decor. The home has every experience- sunroom, spacious patio, balcony, and open concept where you feel like your outdoors even when inside the home. The trail to the ponds was also a wonderful walk. Overall, HIGHLY recommend because it was an outstanding home and also the host was top notch. Thank you for the wonderful memories.
Stayed 4 nights in Jun 2023
Verified

10/10 Excellent

Jennifer W.

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

Fabulous Home, Amazing Weekend

This home did not disappoint. From the moment you open the front door, you are surrounded by the beauty of the views. It was spectacular. Very, very clean, and communication with the owners was top-notch. We had 11 in our group and there was plenty of room. The kitchen was fully stocked - - we grilled in both nights and had everything we needed. It's also an amazing location for any tourist spot you want to visit. Our family/friends cannot wait to go back! If I could give it more than 5 stars, I would. Thank you so much for sharing your beautiful home!!
Stayed 2 nights in Aug 2024
Verified

10/10 Excellent

Grant M.

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

Friends Weekend

We had an amazing stay in this picturesque home with its stunning interiors and million dollar views. Our friend group enjoyed being close to the wineries near Elizabeth and the short drive to downtown Galena. My husband and I have been coming to Galena together for over a decade and thought this would be the perfect place for a friends outing. The house was great for cooking in the gorgeous, fully stocked kitchen and playing cards / bags by the fire pit. All of the bedrooms were beautiful and very comfortable. Everything was spotless, the decor was unique and beautiful. The furnishings were very comfortable, perfect for reading with a cup of coffee in the morning while looking out at the beautiful view. We loved the pond and all it’s amenities. Thank you for an amazing stay. We hope to be back!
Stayed 2 nights in Aug 2023