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  • Writer's pictureRay Cheselka


When we travel, the type of trip and budget can vary.

Sometimes we might want a bit more luxurious of a stay with really comfortable beds and a super nice shower.

Other times we might just want somewhere clean in a good location.

We've learned over time what we like best, and have been fortunate enough to stay in some incredible top-notch places-both hotels and Airbnb's/VRBO. These places come up in conversation periodically, and when they do we rave about and strongly recommend them.

Here are those places!

The Press Hotel-Mariott Autograph Collection Portland, ME

To kick us off, this was the kind of hotel we were excited to be in and excited to return to. We've grown to trust the Mariott brand. Whenever we just need a nice basic place to stay, we prefer Mariott. They're consistently clean, with really comfortable beds, and they often are priced similarly to other nice hotels in the area.

Every now and again, we'll come across one of their autograph collection hotels. If you see "Mariott Autograph Collection", that is going to be a great hotel, and this certainly was not an exception.


This hotel is in the heart of downtown Portland, within walking distance to the wharf, commercial street.


To stay here, it will likely be between $200-$300 per night, but of course, that can vary depending on when you're there. We got a great deal on this hotel because it was a Tuesday night, only $113. It was also past peak tourist season in the area which typically makes big difference in pricing.

See Pricing and Book The Press Hotel on


The rooms are spacious, with super comfortable beds, a decent view, marble showers with a rainfall shower head, and some cool little touches like alarm clocks that are built like radios that you can connect to with Bluetooth.

The Hotel + Amenities

They have an award-winning chef and restaurant in the hotel, along with a bar that has a phenomenal happy hour (like a lobster roll and glass of wine for $10!!!) While in Portland, we didn't eat at the hotel restaurant, but we did end our nights at the hotel bar with some delicious "purple haze" drinks. The bar in this hotel was a great vibe, felt like you were in a speakeasy almost.

They have all the amenities you'd want, and even a rooftop area you can reserve.

The Grand Hyatt-Vail

The first time we stayed overnight in Vail, we had some guidance from our friends who've lived in the Denver area for years now. It was very early in ski season (December), so we got a great deal on this hotel in West Vail because the lift right next to it was not operational yet.

This place is the definition of luxury. We later found out that it's a 5-star hotel.


West Vail could be considered to be a little out of the way because there isn't much around to do. That's not a problem though because the hotel has a shuttle into Lionshead, Main, and East Vail villages. I think they also have a big SUV that will take you anywhere too-you just need to tip. There is a nice walking trail from this hotel into Lionshead Village.


Normally it's $400+ per night, but like we said we got a great deal on it because it was early-season. We stayed for $280. Hard to believe, but that's a great deal in Vail.

See pricing and book the Grand Hyatt Vail on


Our room's bed was super plush and comfortable. It had a marble shower with a rainfall shower head, a separate bathroom area, and a nook next to the window you could lay in overlooking the front of the mountain and Gore creek that runs through Vail.

The Hotel + Amenities

Walking in there is staff to accommodate you, and a big room next to the bar with glass windows that looks out to the mountain. There's a Moet vending machine in the lobby that you can charge to your room, and a Gessner Restaurant or Fireside Lounge server will walk around if you want to order anything. Like most hotels with pools in Vail, they have a great heated one. If you're staying here during peak season, the lift next to the hotel (Cascade Village) is unbelievably convenient, and arguably worth the extra cost if you're there for a long weekend. To top things off, the hotel also has a Spa. There is valet parking, and a garage where can park yourself if you don't mind a short walk.

A beautiful hotel & spa in the mountains AND it has a champagne vending machine in the lobby... what more could you want?

You will have a great time if you stay here!

Santoniro Villa (Airbnb)-Santorini, Greece

We really lucked out with this place.

Of course, going to Santorini, you want to do it right. We were there for about 5 days, and our criteria was to have one of those cool white houses (Cycladic), with a view. Boy did this place exceed the criteria.

When landing in Santorini, the excitement is something you can't really explain. Flying over the blue waters with random islands here and there, then all of the sudden you're landing on one of them. We were greeted with basically a chauffeur, who took us to the villa. We were met by the kindest older woman, Vanda, who gave us a tour of the villa and explained how to go about the island.


This villa was on the cliffs of Thira right next to a phenomenal restaurant 1500bc that we ate at with our favorite server ever, George. Next to that restaurant was a small local market where we got beer, wine, and some snacks. We parked our 4 wheelers (normal to travel around the island on them) right by that market with no problem. If you walk a bit further (5 minutes) you're in the main strip of Thira. You can follow that strip to find a ton of shops, restaurants, and those classic Santorini caldera views.

We actually hiked from Thira, all the way to Oia, and then rode 4 wheelers back. Took a while, but it isn't out of the question if that's your sort of thing. What we're getting at is that it's in prime location! Near everything, quiet, and exactly what you're looking for out of a place to stay in Santorini. The only thing it didn't have was a pool, but you can go to one of the many different colored sand beaches if you want to catch some sun and periodically cool off. The beach towns are cool in Santorini.


This Airbnb is over $400 per night, but it has 3 bedrooms, so if you're with some people it is reasonable. We have 4 people while we were there but this place could sleep 6-7.

View pricing and book the Santoniro Villa on

The Villa + Amenities

We booked this Villa through Airbnb, it was called "Santoniro". Multiple levels, multiple patios, spa-like showers, clean, comfortable, close to everything.

The villa was all white, had 3 bedrooms, 2 bathrooms, and the best part was the rooftop patio. You had a clean look at the caldera for sunsets, watching boats travel in and out of the harbor, and really you could see across the island. It was truly amazing and we think about it often.

We've been dreaming about going back to Santorini ever since we stayed here.

Hotel Capitan Suizo-Tamarindo, Costa Rica

Looking for a Valentine's Day trip? A tropical getaway where everything you need is on-site? Pretty much guaranteed good weather in the dry season? Look no further than Costa Rica.

For us, it was a 5-hour direct flight into Liberia (LIR) airport, and then a 1.5-hour drive to Tamarindo. We were greeted by a friendly staff, our room was very clean, spacious, and nice. On top of that, it had a powerful AC unit to keep it cool from the humid outdoors.


This hotel is in the southern part of Tamarindo, barely on the outskirts of town. It was a walkable distance along the beach into "downtown" Tamarindo.


We stayed for around $220 per night on our mini honeymoon.

See pricing and book Hotel Capitán Suizo on


We got in at night and awoke in the jungle. In our room you walked in, bathroom to the right, storage to the left (with a safe), then there was a door to get into the main area. There, we had our bed, counter space, a mini-fridge, a sitting area a few steps down, and a bit further out to the balcony. This balcony was private, and you looked out to a mini-forest. We saw a monkey swing by on the first day!

The Hotel + Amenities

Having free breakfast, we made our way to where it was served. When we got to the pool, a view of the ocean opened up you're right there on the sand! There is a bar, and seating where they serve breakfast, lunch, dinner, and drinks. You can sit "inside", or at a table in the sand. At night it's covered in lights and you eat dinner (El Barco Restaurant) while listening to the waves. Doesn't get much better than that!

We got a great massage on-site that was reasonably priced, and outside. They also offered kayak rentals, you could definitely ride some horses on the beach, and people will come up selling coconuts (water) for less than $2. It's heavenly.

If you feel like leaving the hotel, you can quickly get into town, and there are a lot of restaurants and bars. There are plenty with views of the water. Grabbing some drinks or food on a patio to watch the sunset will make sure you're fully relaxed.

LOVED this hotel and Costa Rica.

The Hilltop Lounge (Airbnb)-Sedona, Arizona

Sedona is a great place to visit. We've floated the idea of retiring there already because it is so beautiful and peaceful. This house was in the perfect place to fully enjoy it.


This Airbnb is right in the middle of Sedona on the side of the hill and close to the airport. You can get from one end of town to the other in 10-15 minutes, everything is nearby!


After all of the fees and taxes, it ended up being around $325 a night. It has 3 bedrooms, so with a group, it is very reasonable.

See pricing and book the Hilltop Lounge on

The House + Amenities

In this Airbnb, you can wake up and have your coffee every day looking directly at the huge red rock wall that includes Capitol Butte and Chimney Rock. It's stunning.

On that very same patio at night, kick back and lookup. Sedona is a dark sky city, so all the lights face down and after a certain time and people have to shut certain lights off to minimize light pollution. The result is a crystal clear sky where you will very likely see the milky way, shooting stars, comets, satellites, and maybe even some aliens. ;) ( just kidding... or are we?!)

The bedrooms in this Airbnb are very cozy, some have big windows that make you feel like you're outside, and the bathrooms utilize a lot of tiles that make you feel like you're in a spa. You can eat and drink with views, all from your Airbnb.

From riding dune buggies to jeep tours, hiking, or just hanging out and relaxing---Sedona is a must-visit! Build it in with a trip to Phoenix/Scottsdale, or Flagstaff and the Grand Canyon.

Coming Soon-The Hilton Tahiti

What's your favorite hotel? Have you stayed in any of these places?

We'll be adding to this post, or make additional posts like this over time!

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