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"Upside" New Cottage w Custom Built Bunk Room - Inside LKSD Gates

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Front Exterior
Front Exterior
Front Exterior
Front Exterior
Front Exterior

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
4 bedrooms2+ bathroomsSleeps 152614 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View in a map
Lakeside Marblehead, OH
  • Place, Lakeside Daisy State Nature Preserve
    ‪2 min drive‬
  • Place, Kalahari Waterpark Resort
    ‪25 min drive‬
  • Place, Cedar Point
    ‪32 min drive‬

Rooms & beds

4 bedrooms (sleeps 15)

Bedroom 2 - 2nd Floor

1 King Bed

Bedroom 3 - 2nd Floor

1 Queen Bed

Bunk Room - 2nd Floor

+2
3 Single Beds and 3 Single Bunk Beds

Primary Bedroom - 1st Floor

1 King Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Toilet

Bathroom 2

Toilet · Shower only

Bathroom 3

Bathtub or shower · Toilet

Bathroom 4

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Garden

About this property

"Upside" New Cottage w Custom Built Bunk Room - Inside LKSD Gates

Open the Dutch door, let in the lake breeze, and get ready for your perfect vacation in Lakeside at “Upside”. Just steps from breathtaking views of Lake Erie and all that the Lakeside Chautauqua has to offer.

Spend your days enjoying swimming, playing pickleball and shuffleboard, strolling the tree-lined streets, or simply sipping a lemonade on the screened-in front porch. Take in a beautiful dock-side sunset each night and indulge in a sweet treat from one of the local ice cream shops.

About the Space:
‘Upside,’ our newly constructed 4-season cottage, featuring 4 bedrooms and 3 full bathrooms. Discover the well-appointed indoor and outdoor living spaces, modern amenities, and everything you need for a relaxing stay in Lakeside with friends and family.

This home has all the charm of a historic lake cottage but with modern conveniences. Perfectly situated in the heart of Lakeside.

This cottage is ideal for a large group and/or extended families, with plenty of room for children to play and adults to relax. The interior is airy and beautifully appointed with central heating and air, making this a perfect year-round destination.

The first floor boasts an open-plan living room, dining area with seating for 15, a well-stocked kitchen with a dishwasher and spacious counter tops, perfect for making family meals.

The primary bedroom completes the first floor with an ensuite bathroom. Laundry is also conveniently located on the first floor with a new washer and dryer.

Upstairs, you will find 2 bedrooms which share a full hall bathroom and a custom-built bunk room with ensuite full bathroom that will quickly become a favorite spot for the kids to unwind after a fun-filled day.

The house can comfortably sleep 15.

Bedrooms (all new mattresses)
Primary Bedroom (king) with ensuite bath; first floor
Bedroom 2 (queen); shared hallway bath; second floor
Bedroom 3 (king); shared hallway bath; second floor
Bunk room (3 Twin XL bunk beds with trundles, totaling 9 Twin XLs) with ensuite bath; second floor

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

Frequently asked questions

Does "Upside" New Cottage w Custom Built Bunk Room - Inside LKSD Gates have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at "Upside" New Cottage w Custom Built Bunk Room - Inside LKSD Gates?

As of 6 Apr, 2026, prices found for a 1-night stay for 2 adults at "Upside" New Cottage w Custom Built Bunk Room - Inside LKSD Gates on 22 Apr, 2026 start from S$762, 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.

Is "Upside" New Cottage w Custom Built Bunk Room - Inside LKSD Gates pet-friendly?

No, pets are not allowed at this property.

How much is parking at "Upside" New Cottage w Custom Built Bunk Room - Inside LKSD Gates?

On-site parking is available at the property.

What time is check-in at "Upside" New Cottage w Custom Built Bunk Room - Inside LKSD Gates?

Check-in begins at 4:00 PM.

What time is check-out at "Upside" New Cottage w Custom Built Bunk Room - Inside LKSD Gates?

Checkout is at 10:00 AM.

Where is "Upside" New Cottage w Custom Built Bunk Room - Inside LKSD Gates located?

Situated on a lake, this cottage is 0.3 mi (0.5 km) from Lake Erie and within 3 miles (5 km) of Lakeside Daisy State Nature Preserve and Marblehead Lighthouse State Park. Marblehead Lighthouse is 2.3 mi (3.6 km) away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
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

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Christine H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property, every amenity was available. Host was fabulous and easy to reach. Comfortable beds, comfortable furniture, beautiful screen porch. We truly enjoyed our stay.
Stayed 5 nights in Sep 2025
Verified

10/10 Excellent

Beth S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely wonderful! We could not have loved this home more! A huge thank you to the hosts for making sure this home had everything we could ever need! We hope to be back soon!
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Ann H.

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

Great Place!

Our team of 6 and parents loved staying here! Plenty of room for everyone, enough bathrooms and gathering spaces. very thoughtful layout of house and amenities. We hope to stay there again!
Stayed 2 nights in Apr 2024
Verified

10/10 Excellent

Paul K.

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

Awesome place

excellent in everyway-fully stocked, excellent location, plenty of space. if you can book this home, don't hesitate
Stayed 2 nights in Oct 2023
Verified

10/10 Excellent

Christine G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, well equipped, great layout, nicely appointed. Great location and wonderful lake time vibe. Perfect for us nine women who have been friends since kindergarten. Loved the comfy bunkroom room. Small vintage frig in kitchen charming! Host replied quickly to any questions. High marks!
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Carol W.

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

Perfect!

This house is great! Second year 11 long time friends have stayed here. Beautifully decorated, great location, well stocked, and clean! We love this place.
Stayed 3 nights in Sep 2024
Verified

10/10 Excellent

Denise A.

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

Wonderful!

Beautiful home and perfect for us to spend a few days together. We love the bunk room and personal touches!
Stayed 3 nights in Nov 2023
Verified

10/10 Excellent

C S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome experience! Definitely a 5 out of 5! This cottage in Lakeside is so well-equipped and beautiful. We spent a lot of time on the spacious screened porch. The large table allowed all 15 of us to eat together. There were even many games for the kids to play. And of course Lakeside can’t be beat for the lake views, ice cream parlors, and playgrounds. We would stay here again!
Stayed 4 nights in Aug 2025
Verified

10/10 Excellent

Carol W.

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

Perfect House

11 long time friends had our yearly get away at this great house. Wonderful location, stocked with everything you could need and beautifully decorated. The owner was very helpful and responsive! Loved our stay!
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Amber P.

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

Best little family getaway

The entire family cannot say enough good things about this place! The communication from the owner was super quick and the house was amazing! Super clean and within walking distance (about 0.5 miles) from the lake and cute shops! 10/10 would recommend
Stayed 2 nights in Sep 2023
Verified

10/10 Excellent

Genevieve B.

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

Great house

Very well appointed and design touches hit all the high marks. Clean and roomy. We were all pleased.
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

Susan H.

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

Wonderful Lakeside

Upside is a wonderful property close to the pool and all that Lakeside has to offer. Lakeside is the best place to go for a family vacation and Upside makes your time there so comfortable.
Stayed 9 nights in Aug 2023
Response from VrboOwner on 7 Sept, 2023
Thank you! We hope to host you again soon :)
Verified

10/10 Excellent

Tanya M.

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

Upside girl’s weekend

This cottage was the perfect setting for our getaway! The owners did not miss a beat! Highly recommend this gem of a cottage in the quaint Lakeside community! We will definitely return!
Stayed 2 nights in Sep 2023
Verified

10/10 Excellent

Cara A.

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

Attention to details makes all the difference

The property is beautiful and the owners have thought of everything. We have traveled to Lakeside almost every summer and this is quite possibly the nicest home we have stayed in.
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

carol g.

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

Upside

The property is amazing. The location is excellent in Lakeside community, very close to the wellness center and swimming pool.
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Cheryl C.

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

Family getaway

We so enjoyed our stay at “Upside”. Everything was well prepared for our visit and very welcoming. The grandchildren did not want to leave. The owners thought of everything. We will definitely be returning.
Stayed 4 nights in Sep 2023
Verified

10/10 Excellent

Kim K M.

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

Amazing home and stay

Can’t say enough about how beautiful, clean, and comfortable this house is. The kids LOVED the bunk room. Tons of space and bathrooms. Trudi thought of everything to make the stay convenient and homey. Gorgeous, gorgeous house. Flexible, kind, and communicative hosts. Best place we’ve ever stayed!!
Stayed 3 nights in Dec 2023
Verified

10/10 Excellent

Emmy P.

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

Lovely getaway in Lakeside/Marblehead

The house was excellent, so beautiful and well designed! A screened front porch to relax in, a wonderful kitchen and living room, the most awesome bunk room for the kids in our group and plenty of space for our family vacation. The house is a short walk to the water and town amenities (Lake side walking path, park, playground, pier and Pavilion, mini golf, and more); Very close to restaurants, the Kelley's Island Ferry and the beautiful Marblehead Lighthouse-- excellent area to spend time!
Stayed 2 nights in Apr 2023
Response from VrboOwner on 30 Jun, 2023
Thank you! Hopefully you can come visit again! :)
Verified

10/10 Excellent

Caralyn D.

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

Best place in Lakeside

Just a couple of sisters and their families from Idaho and Wyoming who feel blessed to have found upside. It was clean, fun and family friendly. The bunk room and the kitchen were perfect and Trudi was amazing to work with. Quick responses and has thought of everything!
Stayed 3 nights in Apr 2024
Verified

10/10 Excellent

Daniel M.

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

Lakeside house

We had a great stay at the Upside Cottage. The house was perfect for the 11 of us. The design and open living areas were great for relaxing and hanging out together. It has a great porch and a garage that stored our paddleboards and kayaks. The place is as beautiful as the pictures indicate. Trudi is very responsive and helpful.
Stayed 7 nights in Jun 2023
Response from VrboOwner on 30 Jun, 2023
Thank you! We hope to host you again next summer. :)
Verified

10/10 Excellent

katy j.

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

Lakeside in March

Beautiful home. Trudi’s attention to detail is amazing. From supplies to decorations this home and host are exceptional. Communication was great and we truly appreciated all she did to make our stay wonderful;) we are already reviewing calendars to stay again.
Stayed 2 nights in Mar 2024
Response from VrboOwner on 7 Mar, 2024
Thank you so much! We look forward to hosting you again soon.
Verified

10/10 Excellent

Lynn W.

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

Outstanding

Trudy and Kevin, Have a beautiful home. Their attention to detail was outstanding, every need of their guests are met. The house is supplied with anything a guest might need. Lots of equipment and activities to keep the kids busy. We were there on a rainy weekend and the kids were still very entertained! We have stayed at many VRBO properties and we would rate this home at the top! Wonderful vacation home!
Stayed 2 nights in Oct 2023
Verified

10/10 Excellent

Steve D.

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

Loved it

Absolutely loved our stay at "The Upside" in Lakeside, Ohio! The bunk bed room was a hit with the kids, and the layout of the house was awesome. We spent countless hours on the big porch, and the bedrooms were amazing. Plus, the house was fully stocked with everything we needed. Only downside? It was so nice that no one wanted to leave!
Stayed 7 nights in Aug 2023
Response from VrboOwner on 26 Aug, 2023
Thank you! We hope to host you again soon :)
Verified

10/10 Excellent

Lisa P.

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

Just a wonderful property!

The owners have created the perfect Lakeside home for a family getaway. Beautiful first flloor bedroom suite and three bedrooms upstairs including the most exquisite bunk room you've ever seen, complete with sleeping curtains and a"camp lantern" night light for each of the six beds! No detail missed when decorating and furnishing this home. 1/2 block to the big new pool complex, 3 min golf cart ride to beach, shuffleboard shopping. Great communication with friendly owners!
Stayed 7 nights in Aug 2023
Response from VrboOwner on 27 Aug, 2023
Thank you! We hope to host you again soon :)
Verified

10/10 Excellent

Lew S.

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

AMAZING Designer Style "Cottage"!

The Upside was AMAZING! It was like walking into a designer's home. Our grandchildren loved the bunk room. It was their private getaway to regroup and reconnect with each other. The open family design was inviting and met our family's needs exactly. The proximity to the tennis courts and Aquatic Center was perfect for our "tweens". Trudi was so welcoming and gracious whenever we had any concerns or questions. We loved it and hope to return next year!! Best place we've stayed in Lakeside in the past 70 years!
Stayed 7 nights in Jun 2024

About the host

Hosted by Trudi Westendorf

Host profile image
We're the Westendorf's, and we are so excited to be part of the Lakeside Community. Our family of 4 visited for the first time in 2018 and instantly feel in love with the magic of Lakeside.

Simply stated, there is something for everyone and a slower pace where the days go by quickly, and we accomplish nothing except for spending time together, relaxing and rejuvenating.

Enjoy “Upside” our new family cottage in the heart of Lakeside steps from the pool and our families favorite; the pickleball courts.

Why they chose this property

Start your morning on the front porch, perfect for enjoying coffee from Coffee and Cream and fresh donuts from The Porch, two Lakeside favorites!

“Upside” is conveniently located just steps from the Grindley Aquatic Center and pickleball courts and is just a few blocks away from the lakefront, where you can walk along Ohio’s Most Beautiful Mile or rent a kayak, sailboat, or paddle board.

The kids can enjoy one of the nearby lakefront playground areas, a game of mini golf, or the teen center. Visit the shuffleboard courts for a favorite Lakeside family pastime.

Take advantage of the mini golf cart shuttle stops located throughout the community. Golf carts can also be rented through Sypherd Cycles & Rental Center. There is parking for two cars in front of the cottage, which is a bonus as parking is limited within the gates!

Come and discover the magic of Lakeside. See why families return year after year to vacation in this historic gated cottage community on Lake Erie, where time slows down. You will find quaint shops, restaurants, and activities for all ages.

Many of the homes are owned by families with connections to Lakeside that go back more than 3 generations. Even if this is your first visit to Lakeside, you will quickly feel the strong sense of tradition and deeply held community spirit.

The Chautauqua summer season runs from Memorial Day weekend through Labor Day and requires additional admission and parking to enter the gates. These passes allow you to enjoy a wide variety of amenities, activities, and experiences. Be sure to visit lakesideohio.com for current fees and options to purchase ahead of time to reduce wait time at the gates. Also check the Calendar of Events on the website to find the latest arts programming, entertainment, and events.

What makes this property unique

During the Lakeside season (Memorial Day – Labor Day) hundreds of arts programs, entertainment, and activities are available to all guests. Daily gate fees are required. Visit lakesideohio.com for current fees.

Be sure to pick up the newspaper on the way in the gates and join the email list lakesideohio.com to stay up to date.

We are excited to make Lakeside and “Upside” your home away from home for years to come!

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