Downtown Vacations

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Price found within the past 48 hours. Click for updated prices.
  • Jul 31 - Aug 5

    Furnished Apartment Near Longwood + Flight

    North Brookline
    5 nights
    3.0 star property
    7.4/10 - Good (3 reviews)
    "The owners of this property canceled on me the night before my trip, blaming it on a “maintenance issue”. They originally reassigned me to a different unit but then canceled it in full. It was difficult to contact the property and I did not even receive a full refund. Would not recommend staying at this place, a would not recommend this ownership group that works through Evonify Stays."
    Reviewed April 7, 2026
    Roundtrip Chicago (ORD) - Boston (BOS)
    ORD - BOSNonstop BOS - ORDNonstop
    Save 100% on your flight
    $1,413
    $931
    per traveler
    found 1 day ago
    Furnished Apartment Near Longwood
  • Jul 31 - Aug 5

    The Inn at Hastings Park, Relais & Chateaux - Boston + Flight

    Lexington
    5 nights
    4.0 star property
    9.6/10 - Exceptional (256 reviews)
    "Splendid bed and breakfast"
    Reviewed April 29, 2026
    Roundtrip Chicago (ORD) - Boston (BOS)
    ORD - BOSNonstop BOS - ORDNonstop
    Save 100% on your flight
    $1,694
    $1,023
    per traveler
    found 8 hours ago
    The Inn at Hastings Park, Relais & Chateaux - Boston
  • Jul 16 - Jul 19

    Boston Harbor Hotel + Flight

    North End
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,004 reviews)
    "Wonderful classic harbor front hotel. Very nice front desk. Would stay again"
    Reviewed May 25, 2026
    Roundtrip Atlanta (ATL) - Boston (BOS)
    ATL - BOSNonstop BOS - ATLNonstop
    Save 100% on your flight
    $1,814
    $1,175
    per traveler
    found 1 day ago
    Boston Harbor Hotel
  • Jul 14 - Jul 21

    Briar Barn Inn + Flight

    Rowley
    7 nights
    3.5 star property
    9.6/10 - Exceptional (802 reviews)
    "Every aspect of the rooms and service had an extra level of thought behind them. The Nespresso machines were a nice surprise. The lobby had ice all the time so make iced coffees; they were great for on-the-go mornings. The toiletries and diffusers all used very pleasant essential oils that were calming and not intrusive."
    Reviewed May 25, 2026
    Roundtrip Rockford (RFD) - Boston (BOS)
    RFD - BOS1 stop BOS - RFD1 stop
    Save 100% on your flight
    $1,543
    $1,013
    per traveler
    found 1 day ago
    Briar Barn Inn
  • Jul 14 - Jul 21

    Ashworth by the Sea + Flight

    Hampton Beach
    7 nights
    3.0 star property
    8.2/10 - Very Good (1,325 reviews)
    "Nice updated rooms. Little on the small side but overall very nice place to stay."
    Reviewed May 25, 2026
    Roundtrip Rockford (RFD) - Boston (BOS)
    RFD - BOS1 stop BOS - RFD1 stop
    Save 100% on your flight
    $1,658
    $1,109
    per traveler
    found 1 day ago
    Ashworth by the Sea

Where to stay in Downtown

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

Downtown Hotel Deals

Hilton Garden Inn Portsmouth Downtown

Hilton Garden Inn Portsmouth Downtown

3 out of 5
100 High St Portsmouth NH
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $177 total per night from Jun 14 to Jun 15
$177 total
Jun 14 - Jun 15
Total with taxes and fees
8.6/10 Excellent! (352 reviews)
"Both USB ports in the room were not working so I had a dead phone by morning- I forgot my AC adapter. Also the tub and shower looked dirty so I did not use it. Not what I expected for an otherwise newer looking property."

Reviewed on May 26, 2026

Hilton Garden Inn Portsmouth Downtown
Hampton Inn & Suites Portsmouth Downtown

Hampton Inn & Suites Portsmouth Downtown

3 out of 5
23 Portwalk Pl Portsmouth NH
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $165 total per night from Jun 14 to Jun 15
$165 total
Jun 14 - Jun 15
Total with taxes and fees
9.4/10 Exceptional! (1,141 reviews)
"Had an excellent stay in the Hampton Inn and Suites - would highly recommend based on service cleanliness and location. a short walk into the town and everything within walking distance. The staff are amazing and extremely helpful. I had a late flight on the day i was leaving and they had no issue ..."

Reviewed on May 25, 2026

Hampton Inn & Suites Portsmouth Downtown
The Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
40 Court St. Portsmouth NH
Fully refundableReserve now, pay when you stay
$241 nightly
The price is $261 total per night from May 31 to Jun 1
$261 total
May 31 - Jun 1
Total with taxes and fees
9.4/10 Exceptional! (1,000 reviews)
"Wonderfully appointed room so close to walkable downtown. A quintessential New England Home with amazing public spaces in Red, White and Blue historical Americana. Beautifully designed, comfortable. The staff was very pleasant, aim to please and put on a very nice included elevated continental ..."

Reviewed on May 26, 2026

The Hotel Portsmouth
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.

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Things to do

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