We’ll be honest with you: booking a vacation rental can feel like a bit of a gamble. The photos look great, the location seems perfect, the price fits your budget — but you don’t really know what you’re walking into until you’re standing at the door with your bags. Are the towels included, or should you have packed your own? Is there a bedroom on the ground floor for Grandma, or is she about to climb two flights of stairs with a suitcase? Will the kids be restless by day two?
We’ve spent a lot of time thinking about this from the guest side, not just the host side — because we’ve been guests too. Whether you’re headed to the mountains around Asheville, NC or an urban stay near Lake Michigan in Milwaukee, WI, a few minutes of homework before you book can save you a lot of frustration once you arrive. Here’s what we’d actually tell a friend to look for.
1. Basic Amenities at No Extra Charge
Nobody wants to feel nickel-and-dimed for basics that should just come with the stay. Before you book anywhere, it’s worth checking the listing (or simply asking the host) whether these are included:
- Toiletries — shampoo, soap, conditioner, lotion, Q-tips, toilet paper
- Coffee, tea, sugar — a small thing, honestly, but a stocked coffee bar makes that first morning so much easier
- Bath and pool towels — especially if you’re a bigger group, or headed to a pool, hot tub, or the Lake Michigan shoreline
- Extra linens and bedding — for the pull-out couch, the air mattress, or the cousin who decided to come along last minute
- Basic cooking spices – for those who prefer or enjoy cooking, it’s super helpful to have a bit of olive oil, vinegar, salt, pepper, and some spices available. It’s frustrating to have to buy those items for a short few-days-long stay
To us, this isn’t just about convenience — it’s about hospitality. A host who includes the essentials up front is a host who’s actually thought about what it’s like to be a guest. It’s something we take seriously at each of our properties: what you see in the listing is what you get, no surprise charges for basic amenities.
Typically, every vacation rental will charge a cleaning fee and a pet fee (if they accept pets). But in our opinion, charging a fee for basic amenities is a red flag.
2. Accessibility for Multigenerational Groups
If your trip includes grandparents, young kids, or anyone who has a hard time with stairs, accessibility isn’t a nice-to-have — it’s the difference between everyone actually being part of the trip and someone sitting it out. A few things worth asking before you book:
- Is there at least one bedroom and one full bathroom on the ground floor?
- Are there stairs required just to get in the door, or is there a step-free or minimal-step entry?
- Is the main living space — kitchen, living room, dining area — on the same level as that accessible bedroom?
- If mobility is a real concern, is there a walk-in shower rather than a tub-only bathroom?
We’d especially flag this for mountain stays. A gorgeous Asheville cabin can come with a lot of steps along with that view. Look for listings that spell out ground-floor accommodations clearly, or check with your host, rather than hoping for the best and finding out at check-in. Obviously, this does not matter much if no one in your group has issues with stairs, and in some areas it might be difficult to avoid stairs given the house location, age, topography, etc. However, this is still an important item to keep on your checklist when traveling with a multigenerational group.
3. Entertainment and Gathering Spaces
The best rentals aren’t just a place to sleep — they become part of the vacation itself. When you’ve got multiple generations under one roof, having somewhere for everyone to gather (or scatter, when they need a little space) really matters. Keep an eye out for:
- Games — cards, board games, or a couple of arcade-style games for rainy days and after-dinner downtime
- Outdoor dining space — a table big enough for the whole group, so mealtime isn’t a juggling act and everyone can partake
- Fire pits — simple, but they earn their keep on cool Asheville evenings
- Common areas built for groups — enough seating and a thoughtful layout that lets people be together (think our gigantic firepit at the Lamplighter House where you could comfortably fit your entire group for s’mores 🙂)
A Milwaukee stay near the lakefront might lean into grilling and outdoor alfresco dining. An Asheville stay might center around a fire pit and mountain air. Either way, the right gathering spaces are what turn “a place to stay” into where people actually relax and build lasting memories.
Questions to Ask Before You Book
If you want a quick gut-check on any listing — ours or anyone else’s — run through this list:
- Are toiletries, towels, and linens included, or will I need to bring or pay for my own?
- Is there coffee or tea stocked at the property?
- Is there a bedroom and bathroom on the ground floor?
- How many steps are there to get in the door?
- What’s there for entertainment or gathering — games, a fire pit, outdoor dining, hot tub?
- Are there any extra fees, other than the cleaning fee or the pet fee, not shown in the base nightly rate?
Find a Rental That Checks Every Box
This is exactly the kind of stay we try to build at Bromeliad Homes — stocked essentials, transparency in our listing description, and outdoor spaces made for gathering. A couple of our Asheville-area homes that put this checklist into practice:
Boho House in nearby Leicester has a primary bedroom and bath right on the main level, so nobody in your group has to think twice about stairs. Outside, there’s a hot tub, sauna, mini-golf putting green, and a fire pit for evenings under the stars — plenty of ways for everyone to unwind together, or find a quiet corner of their own.
The Lamplighter House in Candler is built for a crowd that wants to stay busy: a full game room with arcade games and a pool table, a media room with a 98″ screen, a sauna and hot tub, and a fire pit with an outdoor dining table for the nights everyone just wants to sit outside together.
Take a look through our full list of properties, and if you’re not sure which one fits your group, just reach out. We’re happy to help you find the right fit.