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Windham Vacation Packages

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Windham Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Furnished Apartment Near Longwood

Furnished Apartment Near Longwood

3 out of 5
Save 100% on your flight
Price was $1,014, price is now $704 per person
$704
per person
Oct 27 - Oct 31
just found
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Stay at this apartment in Brookline. Enjoy free WiFi, parking (surcharge), and air conditioning. Popular attractions Fenway Park and Harvard Square are located nearby.
Super cute apartment! Stayed the weekend to visit out soon at college. Locations was close to everything beds were super comfortable, would stay here again.

Reviewed on Sep 13, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $1,540, price is now $801 per person
$801
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Save 100% on your flight
Price was $2,112, price is now $1,290 per person
$1,290
per person
Dec 5 - Dec 12
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this family-friendly hotel in Boston. Enjoy free WiFi, a garden, and dry cleaning or laundry services. Our guests praise the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on May 19, 2026

Raffles Boston

Raffles Boston

5 out of 5
Save 100% on your flight
Price was $1,461, price is now $955 per person
$955
per person
Dec 3 - Dec 6
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
Price was $1,146, price is now $773 per person
$773
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
Location is great, customer service is fantastic

Reviewed on Sep 24, 2026

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Save 100% on your flight
Price was $15,766, price is now $10,646 per person
$10,646
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury apartment in Everett. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Encore Boston Harbor and TD Garden are located nearby.

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Save 100% on your flight
Price was $3,976, price is now $2,712 per person
$2,712
per person
Dec 10 - Dec 16
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Just perfect

Reviewed on Sep 17, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Save 100% on your flight
Price was $2,007, price is now $1,419 per person
$1,419
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Copley Square are located nearby.

Windham Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $1,660, price is now $761 per person
$761
per person
Nov 27 - Dec 1
just found
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,540, price is now $801 per person
$801
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,461, price is now $955 per person
$955
per person
Dec 3 - Dec 6
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,146, price is now $773 per person
$773
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)

Windham Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $2,112, price is now $1,290 per person
$1,290
per person
Dec 5 - Dec 12
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $3,365, price is now $2,002 per person
$2,002
per person
Dec 10 - Dec 16
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $3,976, price is now $2,712 per person
$2,712
per person
Dec 10 - Dec 16
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $3,126, price is now $2,140 per person
$2,140
per person
Dec 10 - Dec 16
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Bargain Flight
Wed, Oct 21 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$274 Roundtrip, found 9 hours ago
$274
Roundtrip
found 9 hours ago
Select Bargain Flight flight, departing Wed, Oct 21 from Los Angeles Intl. to Logan Intl., returning Sat, Oct 31, priced at $274 found 9 hours ago
Bargain Flight
Tue, Nov 3 - Sat, Nov 7
PDX
Portland Intl.
BOS
Logan Intl.
$328 Roundtrip, found 17 hours ago
$328
Roundtrip
found 17 hours ago
Select Bargain Flight flight, departing Tue, Nov 3 from Portland Intl. to Logan Intl., returning Sat, Nov 7, priced at $328 found 17 hours ago
Bargain Flight
Mon, Sep 28 - Mon, Oct 5
LAX
Los Angeles Intl.
MHT
Manchester-Boston Regional
$386 Roundtrip, found 5 hours ago
$386
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Mon, Sep 28 from Los Angeles Intl. to Manchester-Boston Regional, returning Mon, Oct 5, priced at $386 found 5 hours ago
United
Wed, Oct 7 - Thu, Oct 29
HKG
Hong Kong Intl.
BOS
Logan Intl.
$851 Roundtrip, found 5 hours ago
$851
Roundtrip
found 5 hours ago
Select United flight, departing Wed, Oct 7 from Hong Kong Intl. to Logan Intl., returning Thu, Oct 29, priced at $851 found 5 hours ago