Downtown Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Downtown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Boston Waltham
Save 100% on your flight
per person
Jun 6 - Jun 10
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Waltham. Enjoy free breakfast, a 24-hour fitness center, and WiFi (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Lexington Battle Green and Walden Pond are located nearby.
Hotel AKA Back Bay
Back Bay
Save 100% on your flight
per person
Jun 6 - Jun 10
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4.5-star luxury hotel in Boston. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Omni Boston Hotel at the Seaport
Seaport District
Save 100% on your flight
per person
Jun 6 - Jun 10
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star spa hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
The Dagny Boston
Downtown Boston
Save 100% on your flight
per person
Jun 6 - Jun 10
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
citizenM Boston North Station
West End
Save 100% on your flight
per person
Jun 6 - Jun 10
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
Top Hotel Deals
Hampton Inn & Suites Portsmouth Downtown
23 Portwalk Pl, Portsmouth, NH
0.23 km from Downtown
Stay at this 3-star business-friendly hotel in Portsmouth. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
The Hotel Portsmouth
40 Court St., Portsmouth, NH
0.3 km from Downtown
Stay at this 3-star business-friendly hotel in Portsmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hilton Garden Inn Portsmouth Downtown
100 High St, Portsmouth, NH
0.19 km from Downtown
Stay at this 3-star business-friendly hotel in Portsmouth. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Sheraton Portsmouth Harborside Hotel
250 Market St, Portsmouth, NH
0.36 km from Downtown
Book a stay at this business-friendly hotel in Portsmouth. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
Residence Inn by Marriott Portsmouth Downtown/ Waterfront
100 Deer Street, Portsmouth, NH
0.3 km from Downtown
Stay at this 3-star business-friendly hotel in Portsmouth. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff ...
Ashworth by the Sea
295 Ocean Blvd, Hampton, NH
18.61 km from Downtown
Stay at this 3-star beach hotel in Hampton. Enjoy 3 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff ...
Anchorage Inn and Resort
265 Long Beach Avenue, York Beach, ME
14.33 km from Downtown
Stay at this 3-star beach hotel in York Beach. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Cliff House Maine
591 Shore Road, Cape Neddick, ME
21.74 km from Downtown
Stay at this 4.5-star luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the ...
Terrace by the Sea
23 Wharf Ln, Ogunquit, ME
23.11 km from Downtown
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Anchorage by the Sea
125 Shore Road, Ogunquit, ME
22.88 km from Downtown
Stay at this 3-star hotel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in ...
Anchor Inn and Cottages Wells-Ogunquit
424 Post Rd, Wells, ME
26.71 km from Downtown
Stay at this motel in Wells. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Hampton Inn Portsmouth Central
99 Durgin Ln, Portsmouth, NH
3.37 km from Downtown
Book a stay at this business-friendly hotel in Portsmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Holiday Inn Portsmouth by IHG
300 Woodbury Ave, Portsmouth, NH
1.6 km from Downtown
Stay at this 3-star hotel in Portsmouth. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Jun 11 - Wed, Jun 18
LAX
Los Angeles Intl.
BOS
Logan Intl.
$180 Roundtrip, found 4 days ago
$180
Roundtrip
found 4 days ago
Thu, Sep 25 - Thu, Oct 9
LAX
Los Angeles Intl.
BOS
Logan Intl.
$280 Roundtrip, found 20 hours ago
$280
Roundtrip
found 20 hours ago
Mon, May 12 - Thu, May 15
PDX
Portland Intl.
BOS
Logan Intl.
$297 Roundtrip, found 5 days ago
$297
Roundtrip
found 5 days ago
Sat, May 10 - Tue, May 13
LAX
Los Angeles Intl.
BOS
Logan Intl.
$297 Roundtrip, found 22 hours ago
$297
Roundtrip
found 22 hours ago
Best points of interest in Portsmouth
- Market Square Vacations
- The Music Hall Vacations
- Strawbery Banke Museum Vacations
- Portsmouth Brewery Vacations
- Seacoast Repertory Theatre Vacations
- Portsmouth Harbor Trail Vacations
- Governor John Langdon House Museum Vacations
- Warner House Vacations
- Portsmouth Athenaeum Vacations
- John Paul Jones House Museum Vacations
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