
Vacations Close To Madison Boulder
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Madison Boulder Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.




Portland Regency Hotel & Spa
Downtown Portland
Price was $1,202, price is now $1,021 per person
$1,021
per person
Nov 12 - Nov 19
found 18 hours ago
Roundtrip non-stop flight included
Dayton (DAY) to Portland (PWM)
Easy access for walking downtown and for driving to destinations. Friendly staff
Loved our trip and stay
Reviewed on Oct 13, 2026

Evalina Hotel
Downtown Portland
Price was $2,069, price is now $1,757 per person
$1,757
per person
Nov 12 - Nov 19
found 18 hours ago
Roundtrip non-stop flight included
Dayton (DAY) to Portland (PWM)
Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed kitchenette — though if you came to Portland for the foodie scene, you might end up just using it for breakfast, as we did. Only sour note was the disco music (coming in via the ventilation system?) from a nearby establishment audible during business hours. Well, if you pick a hotel in the middle of things, you get the noise and bustle that comes from being in the middle of things. That said, we’d come again, but shoot for a penthouse/upper floor unit farther from the street-level mania.
Reviewed on Oct 5, 2026

The Weldon Hotel
Downtown Portland
Price was $1,499, price is now $1,309 per person
$1,309
per person
Nov 12 - Nov 19
found 18 hours ago
Roundtrip non-stop flight included
Dayton (DAY) to Portland (PWM)
This was the best accommodation in Portland that we have stayed at—by a wide margin. The building and unit itself are a dream. Spacious, quiet, elevated, fresh, clean, thoughtful touches, quality finishes and materials, comfortable, inviting, secure…I have nothing but praise for this property. My spouse and I waxed lyrical about it for the entire stay, “Oh my goodness, I wish we lived here.”, and “we’re home!”. Of course we were happy to get back to our real home back in Boston after our time at the Weldon came to a close, but it was sincerely a “home away from home” experience top to bottom. Book this place—you’ve found the one.
Reviewed on Oct 9, 2026


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