Hotel Living for Frequent Flyers: Is It Really Feasible?

by Sky Skylar | March 3, 2025 | 1 Comment

I’ve spent a lot of time exploring the idea of living in a hotel full-time, and you’d be surprised how practical—and even affordable—it can be under the right circumstances. With housekeeping, on-site amenities, and potential cost savings, I’ve seen this lifestyle catch on with remote workers, transitional renters, and digital nomads. From hotel policies to loyalty programs, here are seven things to keep in mind if you’re considering hotel life long-term.

Yes, It’s Legal—But Rules Vary

1. Yes, It's Legal—But Rules Vary

In my searches, I’ve found that while most hotels do allow extended stays, local regulations can significantly differ from one place to another. Some jurisdictions classify long-term hotel dwellers as tenants after a set number of days, which might grant certain rights similar to a standard renter. It’s a fascinating overlap between hospitality law and landlord-tenant regulations that can lead to unexpected benefits—and responsibilities.

According to a 2024 survey by the American Hospitality Association, at least 58% of major city hotels reported hosting guests for 30 days or longer. That’s not surprising given how flexible extended-stay options have become. But it’s important to do your own due diligence. High-profile properties like The Ritz and Chelsea in New York have famously housed celebrities for years, proving it’s possible for the determined (and well-funded) traveler. Still, I always advise verifying local rules and ensuring the property is on board before fully committing to a long-term stay experience.

One friend of mine discovered that in certain cities, staying past the 28-day mark triggers different tax implications. For example, some jurisdictions may waive occupancy taxes after a month, while others shift the legal classification of your stay. This can affect everything from your daily costs to your legal protections. Always check with hotel management and local authorities to avoid surprises.

Amenities Make It Tempting

2. Amenities Make It Tempting

One of the biggest draws to hotel living is the buffet of amenities you won’t typically find in a traditional rental. Daily housekeeping, 24-hour room service, fully equipped fitness centers, and even furnished kitchens in extended-stay brands offer a sort of “vacation mode” lifestyle all year round. This can dramatically reduce daily chores, freeing up more time to focus on work or leisure.

I’ve seen firsthand how pet-friendly extended-stay suites—equipped with full kitchens and in-room laundry—can make all the difference. A colleague once moved into such a setup during an in-between-jobs phase and found it so convenient that he extended his stay for several months. Beyond convenience, it can also translate into cost savings if you’re not paying separate bills for utilities, gym memberships, or even streaming services. According to industry data from 2023, extended-stay hotels saw a 12% uptick in bookings from digital nomads, many of whom cited access to on-site amenities as a key deciding factor.

Of course, amenities vary widely by property. Some hotels offer social events for long-term guests, making it easy to meet others who travel for business or adventure. I’ve encountered evening socials that include free snacks and drinks—a nice perk you’d rarely find in an apartment complex. Whether you’re looking for camaraderie or just a hassle-free living experience, the range of services hotels provide can be a major plus.

Expect Unique Cost Calculations

3. Expect Unique Cost Calculations

It might seem expensive at first glance, but there’s more to consider than just the nightly rate. Many hotels, especially extended-stay chains like Residence Inn by Marriott or Candlewood Suites by IHG, offer significant discounts for weekly or monthly bookings. During one of my recent experiments, I managed to negotiate a 20% reduction simply by committing to a longer stay. Also, if you look at high-priced rental markets like New York or San Francisco, the math sometimes tilts in favor of hotel living when you factor in utilities, furnishings, and the value of included services.

According to a 2023 industry report, some digital nomads save up to 15% annually by opting for long-term hotel arrangements rather than traditional leases. Personally, I make sure to factor in the cost of internet, laundry services, gym fees, and even small conveniences like free coffee in the lobby. When I ran the numbers for a San Francisco project last year, living in an extended-stay hotel turned out to be nearly $200 cheaper per month than a typical one-bedroom rental, mostly due to these hidden savings.

Beyond advertised discounts, it pays to get creative. I’ve had success using loyalty program points, leveraging discount travel apps, and even negotiating directly with hotel managers. Some frequent guests also earn enough points to eventually enjoy completely free nights. Before you commit to a new city or a multiple-month stay, reach out to various properties to see what sort of deals they’re willing to offer—most places are eager to fill rooms and keep consistent revenue streams.

Downsizing and Organization Are Essential

4. Downsizing and Organization Are Essential

When you choose hotel living, it usually means learning to live with less. I discovered that my closet space shrank drastically, forcing me to adopt a truly minimalist wardrobe. If you’re someone who loves your walk-in closet, be ready for a big adjustment. But there’s also freedom in owning fewer things. I took it as an opportunity to declutter and realized I could travel lighter—and faster—if I needed to relocate to another city.

Effective organization is key. I’ve honed a system of packing cubes for clothes, sturdy zippered pouches for documents, and labeled storage bins for electronics. According to a 2023 consumer trends study, sales of compact storage solutions jumped by 8%, likely due to the rise in nomadic work styles. Hotels may provide limited closets or drawers, so you’ll want to optimize every inch. As for mail and packages, some extended-stay hotels provide dedicated mailboxes or front-desk acceptance services, but be sure to confirm in advance.

Staying in multiple hotels over a span of weeks or months also comes with the challenge of constantly transitioning from one environment to another. I’ve met travelers who rely on self-storage lockers in central locations, allowing them to bounce from property to property without lugging all their belongings. Whether you’re on the move or planning to settle in one hotel for a while, a solid organization system keeps your space feeling more like a home and less like an extended pit stop.

Perks for Frequent Flyers

5. Perks for Frequent Flyers

As someone who’s always tracking reward points, I find the biggest advantage of hotel living to be the cumulative perks. By aligning hotel loyalty memberships with airline programs, you can double-dip on points and miles. Whenever I stay at an extended-stay brand tied to major airline partners, I’m essentially stacking points that translate into free flights and upgraded rooms.

According to a 2024 survey by a leading travel research group, around 70% of frequent business travelers say they have at least one hotel chain loyalty membership. Living in the same chain for a few weeks or months can quickly bump you up to elite status. In my case, I’ve enjoyed perks like room upgrades, free breakfasts, and late checkouts that have saved me both time and money. It’s a game of strategy: the more nights you stack with a single brand, the faster the premium benefits unlock.

Simultaneously, watch out for special promotions. Airlines often run tie-in deals with hotel chains, offering bonus miles if you book extended stays. This synergy means every stay might bring you closer to a free weekend getaway or a first-class upgrade. If you’re serious about turning your long-term hotel investment into tangible travel rewards, I highly recommend regularly checking loyalty program newsletters and travel blogs for the latest bonus promos.

Weigh the Potential Downsides

6. Weigh the Potential Downsides

Not everything about hotel living is sunshine and room service. Unlike a traditional lease, you often don’t have the same tenant protections, which can be a problem if a hotel decides to change its policies or rates unexpectedly. I recall one instance where a friend was abruptly asked to relocate because the hotel was overbooked for a special event weekend. Without tenant rights, there’s less leverage to demand a stable arrangement.

Noise can also be an issue. Hotels, particularly those near airports or in bustling downtown districts, can see a constant stream of new arrivals at all hours. I’ve learned to pack earplugs and even a small white noise machine to cope. Then there’s the question of customizing your space. Hotel policies might prevent you from decorating the walls or bringing in your own furniture, so it takes creativity to make a hotel room truly feel like home.

Living abroad in a hotel long-term has its own complexities, such as potential visa restrictions or residency rules that might require you to leave periodically. Personal logistics can be tricky too. Without a permanent address, you may need extra planning to handle important mail, official documents, and even some online subscriptions. Balancing these downsides against the convenience factor is essential to avoid any unwelcome surprises down the road.

Extended-Stay Options and Alternatives

7. Extended-Stay Options and Alternatives

If a full-service hotel doesn’t check all your boxes, there are alternatives worth exploring. Serviced apartments and long-term Airbnb rentals can offer more personalized spaces, sometimes with separate living rooms or even private outdoor areas. I’ve rented a few of these in the past, especially when I needed a home-like setting for a remote work project. While they might cost less than a high-end hotel, you’ll often forgo daily housekeeping and robust loyalty rewards.

Extended-stay hotels strike a middle ground, particularly for travelers who live on the road but appreciate the security of a front desk and housekeeping staff. Many of these properties also cater to social needs, hosting networking events and informal gatherings that help you meet fellow travelers. According to a 2023 review aggregator, extended-stay brands consistently earned high marks for safety and community-building.

Before deciding on any option, do a bit of legwork: read property reviews, check local laws, and evaluate the neighborhood’s safety rating. Some travelers prefer the anonymity and independence of peer-to-peer rentals, while others value the consistency of a well-known hotel chain. Finding the right balance depends on your budget, comfort level, and personal style of travel. In my experience, a little research can go a long way in securing the best deal and an environment that feels like home.

Final Thoughts

Final Thoughts

Deciding to live in a hotel isn’t a casual choice. It takes careful budgeting, research, and a willingness to adapt to a non-traditional lifestyle. But for those who crave flexibility and enjoy the built-in perks of housekeeping, on-site amenities, and loyalty rewards, long-term hotel stays can truly be a game-changer. Just remember to do your homework on local regulations, negotiate rates when possible, and weigh the pros and cons in the context of your specific travel needs.

From legal considerations to downsizing possessions, I’ve learned that hotel living shines brightest when it fits a certain lifestyle—mobile, somewhat minimalist, and open to spur-of-the-moment travel plans. If that resonates with you, then you might find this an exciting alternative to a conventional lease or mortgage.

Sky Skylar’s Take

I’ll be honest: when I first heard about living in a hotel long-term, I thought it was a novelty for rock stars and millionaires. But after gathering observations from travelers worldwide, it’s clear that it can be more within reach than you’d expect—especially in an era where remote work thrives, flight routes expand, and loyalty programs grow more generous with each year.

Ultimately, hotel living makes sense for those who value convenience over customization. If you’re the type who wants a unique living space with personal décor, you might feel restricted. Yet for me, the ability to accumulate points, enjoy daily housekeeping, and have the option to pick up and move without breaking a lease outweighs the sacrifice of permanent walls and a walk-in closet.

Stay connected with our travel community on BoardingArea.

Also on BoardingArea
Frequent Miler
Capital One Venture Rewards Credit Card Review (2026)
The Capital One Venture Rewards card is the OG of the bank’s “miles-based” offerings. Over the last few years, Capital One has greatly strengthened its transfer partners, making this not only a card that earns 2% everywhere towards travel, but also 2x everywhere in transferable currency. Let’s take a closer...
View from the Wing
Why Bilt Rewards Cardholders Were Furious Over Lost ‘Free Points’—And Missed Out On Even More Value
Bilt Rewards cardholders were furious when the company replaced their easy 'free points' earned from paying rent—but in their outrage, many overlooked new benefits and higher value that could actually leave them better off. Here's what went wrong in the rollout, why consumers were so angry, and what analysts...
Live and Let’s Fly
United First Class Passenger Ordered Off Flight After Clash With Off-Duty Flight Attendant…Then Flies Anyway
A viral video shows a heated exchange over perceived rudeness toward a hearing-impaired woman on a United Airlines flight, with a paying customer being asked to deplane. Even though the passenger ultimately flew, it’s fair to ask why this whole incident ever occurred in the first place. United Passenger Asked...
Frequent Miler
Get 5,000 Frontier Miles for free (act fast)
Frontier has a new promotion called “The Big Redemption,” which gives members up to 5,000 miles for free.  All you have to do is fill out a form, take a screenshot showing that you have miles in another program, and send it to Frontier. It will then match those miles,...
Your Mileage May Vary
I Was Today Years Old When I Learned Why My Sunset Photos Looked “Fine”
I was today years old when I learned that most of the reason my sunset photos looked fine — but never quite right — wasn’t the sunset. It was my…
Frequent Miler
Barclays JetBlue Plus Card: Improved 70K Welcome Offer
Barclays has an improved offer out for the JetBlue Plus Card, awarding a total of 70,000 TrueBlue points after spending $1K within the first 90 days. Complete Guide to JetBlue TrueBlue The Offers & Key Card Details For more information about these cards and to find a link to apply,...
One Mile at a Time
American A319s & A320s Get More First Class Seats, But It’s Not All Good News
In March 2024, American Airlines announced plans to retrofit its Airbus A319 & A320 aircraft, to add more first class seats. This announcement coincided with American ordering 260+ Airbus, Boeing, and Embraer jets. There’s now an update, as the first retrofitted plane with new interiors is expected to be in...
Miles To Memories
United’s Big Glitch, Hyatt’s All Inclusive Boom, Easy Bilt Calculator & Best Hotel Promo?
Delta with Amex credits, United's big glitch, easy Bilt calculator, Hyatt grows even more & new Bonus Journeys! The post United’s Big Glitch, Hyatt’s All Inclusive Boom, Easy Bilt Calculator & Best Hotel Promo? appeared first on Miles to Memories.
Miles To Memories
New Chase Offers for Uber, Lyft, Gas Purchases & More
Check your Chase credit cards for new offers that can save you 10% on Uber and Lyft rides, $30 on a Turo rental, 20% back on gas and more. The post New Chase Offers for Uber, Lyft, Gas Purchases & More appeared first on Miles to Memories.
One Mile at a Time
American Launching A321XLR Flights To Porto, Portugal… But Only In Mid-2027
American Airlines has just announced its newest transatlantic route, which doesn’t come as much of a surprise, except for the unusual timing of the announcement…
The Gate with Brian Cohen
As Low as €22.00 or 3,675 Avios Per Flight With Vueling Airlines
Purchase tickets for as low as €22.00 or 3,675 Avios per flight with Vueling Airlines for travel via select routes between Monday, February 23, 2026 and Thursday, March 26, 2026. No promotion code is required... ...but you must... The post As Low as €22.00 or 3,675 Avios Per Flight With Vueling Airlines...
The Bulkhead Seat
American Airlines Launches Porto Flights in Summer 2027
American Airlines is adding a new city in Portugal to its transatlantic network with… The post American Airlines Launches Porto Flights in Summer 2027 appeared first on The Bulkhead Seat.
Frequent Miler
Airbnb Amex Offers: $50 back of 5k points when you spend $250+ (targeted)
There are several new Airbnb Amex Offers out today, the best of which give either 5,000 Membership Rewards points or $50 back when spending $250 or on vacation rentals. I also have one that offers $30 back on the same $250 in spend; I assume that there’s a 3,000-point version...
Paddle Your Own Kanoo
British Aviation Regulator Tells Airlines To Show Passengers The Impact Their Flight Will Have On The Enviroment
Alongside the departure time and airport, the cost of any added extras, and the class of travel, airline passengers in the UK will soon have something else to factor into their decision of what flight to book… the impact it will have on the environment. In new guidance published by...
View from the Wing
American Airlines Pilots Forced To Sleep In Airports—Union Blasts Management As “Completely Unprepared” For Meltdown
American Airlines pilots have joined flight attendants in revealing they were forced to sleep in airports during last week's meltdown, with their union blasting management as "completely unprepared," despite clear warnings ahead of the storm.
From The Tray Table
Why I love JetBlue’s new overpriced and exclusive lounge passes
Two months after opening, JetBlue is now selling day passes to its first-ever airport lounge — and they… The post Why I love JetBlue’s new overpriced and exclusive lounge passes appeared first on From the Tray Table.
Your Mileage May Vary
What Hotel Guests Actually Want vs. What Hotels Keep Giving Us
When you stay at hotels once or twice a year, if that, you’re typically happy with everything you get. A coffeemaker in the room! A lighted magnifying mirror! And OMG,…
Miles To Memories
Frontier Airlines Giving Away 70 Million Miles
From February 5-22, consumers can "swap" unused reward points from other rewards programs and receive up to 5,000 Frontier Miles, enough for an Award flight. The post Frontier Airlines Giving Away 70 Million Miles appeared first on Miles to Memories.
View from the Wing
Best Hyatt Card Bonus In Years — Advertised As 5 Free Nights, You Actually Wind Up With 7
Hyatt is advertising this card bonus as 5 free nights, but the spend required to earn it also triggers the card’s annual Category 1–4 night and generates enough points for another award night. Put it together and the “5-night” offer can realistically turn into 7 nights at Category 1–4 Hyatt...
Frequent Flyer Bonuses
Qatar Airways Privilege Club – Earn up to 5,000 bonus Avios on flights out of China, Hong Kong, or Taiwan (Feb 5 Bonus Offer Highlight)
Today's bonus offer highlight is another bonus offer tied into a seat sale as Qatar Airways is offering up to 5,000 bonus Avios and 20% off flights out of China, Hong Kong, or Taiwan! Check out all of the new bonuses added today: The post Qatar Airways Privilege Club – Earn...
Frequent Miler
Avianca Award Sale: flights to Central and South America starting at ~2,000 miles one-way
Avianca LifeMiles runs regular award sales on its own flights, and it launched its latest this week. Like many of LifeMiles’ sales, there isn’t a set discount percentage, but it seems to cover most, if not all, of Avianca’s US routes. Economy flights from the US to Central and South...
Pointshogger
[INTERVIEW] Points Travel Festival Toronto 2026
Exciting news, fellow BoardingArea bloggers Rapid Travel Chai and Points Miles and Bling (PMB) have teamed up to host the first over Points and Travel Festival in Toronto on April 17 and 18, 2026.  The post [INTERVIEW] Points Travel Festival Toronto 2026 appeared first on Pointshogger.
Miles To Memories
Great Wolf Lodge Sale, Prices Starting from $26/Person
Great Wolf Lodge will run a one-day promotion tomorrow where you can book a suite starting from $26 per person. The post Great Wolf Lodge Sale, Prices Starting from $26/Person appeared first on Miles to Memories.
Points With a Crew
Kickstarter: AERIONN Forma Titanium Carry-On Luggage
The AERIONN Forma is a high-end carry-on suitcase made completely out of titanium. Built to last, it's on Kickstarter, but only for a few more ...

One thought on “Hotel Living for Frequent Flyers: Is It Really Feasible?

Leave a Reply

Your email address will not be published. Required fields are marked *

Categories

Our Bloggers