Rosemont Trip

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Price found within the past 48 hours. Click for updated prices.
  • Restaurant
    Jul 29 - Aug 2

    Hampton Inn Oxford + Flight

    Oxford
    4 nights
    2.5 star property
    9.0/10 - Wonderful (1,000 reviews)
    "You can have dinner/lunch at the Oxbow Pub in the casino across the street. Seriously, a two minute drive away. Most of that will be spent finding a parking spot. Very nice service there. The complementary breakfast is mostly the usual fare of fruit, cereals, small pastries and toast, but I have never seen the make your own waffles bar! Also egg white omelets. Really, just about whatever a normal person might want. My food sensitivities and habits are too weird to be accommodated, so I..."
    Reviewed May 18, 2026
    Return • Chicago (ORD) - Boston (BOS)
    ORD - BOS • Direct BOS - ORD • Direct
    ₹67,887
    ₹58,974
    per traveller
    found 16 hours ago
    Hampton Inn Oxford
  • Lobby sitting area
    Jul 29 - Aug 2

    Ogunquit River Inn & Suites + Flight

    Ogunquit
    4 nights
    3.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    "Great experience all around. Will definitely visit again if in the area."
    Reviewed May 25, 2026
    Return • Chicago (ORD) - Boston (BOS)
    ORD - BOS • Direct BOS - ORD • Direct
    Save 100% on your flight
    ₹144,117
    ₹94,441
    per traveller
    found 16 hours ago
    Ogunquit River Inn & Suites
  • Restaurant
    Jul 29 - Aug 2

    Portland Harbor Hotel + Flight

    Downtown Portland
    4 nights
    4.0 star property
    9.4/10 - Exceptional (1,769 reviews)
    "An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow."
    Reviewed May 25, 2026
    Return • Chicago (ORD) - Boston (BOS)
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    Save 100% on your flight
    ₹164,604
    ₹118,778
    per traveller
    found 16 hours ago
    Portland Harbor Hotel
  • Front of property
    Jul 29 - Aug 2

    Portland Regency Hotel & Spa + Flight

    Downtown Portland
    4 nights
    3.5 star property
    9.4/10 - Exceptional (1,652 reviews)
    "Exactly what we wanted. Quiet, romantic, great location."
    Reviewed May 24, 2026
    Return • Chicago (ORD) - Boston (BOS)
    ORD - BOS • Direct BOS - ORD • Direct
    ₹136,486
    ₹116,396
    per traveller
    found 16 hours ago
    Portland Regency Hotel & Spa
  • View from property
    Jul 29 - Aug 2

    Chebeague Island Inn + Flight

    Chebeague Island
    4 nights
    4.0 star property
    8.8/10 - Excellent (77 reviews)
    "Charming and easy access to the Golf Course "
    Reviewed September 21, 2025
    Return • Chicago (ORD) - Boston (BOS)
    ORD - BOS • Direct BOS - ORD • Direct
    ₹107,128
    ₹92,519
    per traveller
    found 16 hours ago
    Chebeague Island Inn

Where to stay in Rosemont

Find the best Rosemont areas and neighborhoods for the activities you enjoy most. Learn more about Rosemont
Downtown Portland

Downtown Portland

4 out of top 10 points of interest in this area
3.5/5(2 area reviews)

A noteworthy feature of Downtown Portland is its captivating waterfront views. While you're in town, be sure to stop and check out Cross Insurance Arena and Merrill Auditorium.

Find hotels in Downtown Portland

Top hotels in Rosemont

Fleetwood House Bed & Breakfast

Fleetwood House Bed & Breakfast

3 out of 5
10 Fleetwood St Portland ME
The price is ₹21,807 per night from 31 May to 1 Jun
₹21,807
₹23,770 total
31 May - 1 Jun
includes taxes & fees
9/10 Wonderful! (133 reviews)
"Breakfast was excellent! Very pet friendly. Room was lovely and clean."

Reviewed on 17 May 2026

Fleetwood House Bed & Breakfast
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is ₹20,363 per night from 31 May to 1 Jun
₹20,363
₹26,163 total
31 May - 1 Jun
includes taxes & fees
9.4/10 Exceptional! (1,769 reviews)
"An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow."

Reviewed on 25 May 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is ₹18,324 per night from 31 May to 1 Jun
₹18,324
₹20,274 total
31 May - 1 Jun
includes taxes & fees
9.4/10 Exceptional! (1,652 reviews)
"Just okay, guest services staff a bit aloof. Can’t beat the location in the heart of the old port. Comfortable bed. Room service closed too early. Nothing in the minibar fridge. Walls are surprisingly thin. I expected more from the Regency."

Reviewed on 25 May 2026

Portland Regency Hotel & Spa
See all 2,492 properties in Rosemont
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Rosemont holiday package cost?
Custom make your Rosemont package from only . Choose from any combination of rental cars, flights and hotels to put together the getaway you've long been dreaming about. Remember to add on a few experiences or tours!
How do I get a cheap travel package to Rosemont?
Crafting your own Rosemont holiday package with Expedia is such a simple way to save. We have access to more than 550 airlines and 1,000,000 hotels all over the world. With such a huge range to choose from, you'll have no trouble creating your perfect getaway.
Where should I stay in Rosemont?
Most who travel to Rosemont include University of Southern Maine and Portland Museum of Art on their bucket lists. Why not select a hotel within walking distance of these great attractions?
What are the top hotels in Rosemont?
Make a reservation at Fleetwood House Bed And Breakfast. It's one of this area's most popular hotels. Another well-known option in Rosemont is Glamp" Out Near Downtown Portland W.
How far in advance should I book my Rosemont holiday?
Reward yourself with the biggest variety and the cheapest prices by booking your Rosemont adventure early. Airlines tend to publish flights anywhere up to 12 months in advance, so start your planning ASAP. That said, Expedia is dedicated to giving you the best deals around, so it's never a bad time to book your dream holiday!
What does an Expedia Rosemont travel package include?
Travel packages include flights, rental cars and hotels, but you can mix and match them to create your dream Rosemont trip. You can also add on experiences and activities once you've made your booking. You're in the driver's seat! When you bundle your bookings with Expedia, you'll enjoy deals you won't find anywhere else.
What should I know before booking a Rosemont travel package?
Bundling your bookings into a Rosemont holiday package is the most convenient way to organise your trip. Not only that, you'll save big just for combining your hotels, flights and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Rosemont Expedia holiday package?
Yes, you can. Expedia has access to more than 550 partner airlines all over the world, so select the carrier that best fits your budget and travel needs.
If I'm not able to travel, can I cancel my Rosemont holiday package?
Yes you can, and we're here to help. You may be able to cancel or change your Rosemont holiday package at no cost if you booked in the last 24 hours. However, you may incur a fee from your airline, hotel or car rental company for older bookings. If life throws you a curveball, have a look at our Customer Service Portal for more information.

Popular places to visit

East End Beach

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

East End Beach
Eastern Promenade

Eastern Promenade

Built on an old rail corridor along the easternmost portion of Portland’s peninsula, this waterfront trail offers stunning views of the harbor and Atlantic Ocean.

Eastern Promenade
Victoria Mansion

Victoria Mansion

Visit the remarkably preserved 19th-century manor house, located in downtown Portland. Get an authentic impression of life during that era.

Victoria Mansion
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.