Search Deals onThe Wayside Vacation Packages
The Wayside Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Iris Hotel Boston
Save 100% on your flight
Price was $989, price is now $722 per person
$722
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this business-friendly hotel in Brookline. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Fenway Park and Harvard Square are located nearby.
The Coach House
Price was $4,340, price is now $3,458 per person
$3,458
per person
Oct 27 - Oct 31
found 10 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this hotel in Salem. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Salem Witch Museum and Salem Pioneer Village 1630 are located nearby.
The Mansion at Ocean Edge
Price was $1,566, price is now $1,287 per person
$1,287
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Brewster. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Brewster Historical Society Museum and Ocean Edge Golf Club are located nearby.
Fairmont Copley Plaza, Boston
Save 100% on your flight
Price was $2,064, price is now $1,450 per person
$1,450
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Monty Boston
Save 100% on your flight
Price was $2,496, price is now $1,794 per person
$1,794
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)
Stay at this aparthotel in Boston. Enjoy free WiFi, a rooftop terrace, and a garden. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
The Langham, Boston
Save 100% on your flight
Price was $2,330, price is now $1,727 per person
$1,727
per person
Nov 16 - Nov 21
found 19 hours 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.
Raffles Boston
Save 100% on your flight
Price was $2,201, price is now $1,642 per person
$1,642
per person
Nov 16 - Nov 21
found 19 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.
Luxury Apartments by Hyatus at Boston Everett
Save 100% on your flight
Price was $1,133, price is now $846 per person
$846
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
The Newbury Boston
Save 100% on your flight
Price was $2,664, price is now $1,997 per person
$1,997
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Four Seasons Hotel Boston
Save 100% on your flight
Price was $2,595, price is now $1,990 per person
$1,990
per person
Nov 3 - 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.
Encore Boston Harbor
Save 100% on your flight
Price was $1,682, price is now $1,308 per person
$1,308
per person
Nov 16 - Nov 21
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Hyatus Designer Residences Somerville
Save 100% on your flight
Price was $928, price is now $724 per person
$724
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this luxury aparthotel in Somerville. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
3-4 Night Vacations in The Wayside
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in The Wayside
Price found within the past 48 hours. Click for updated prices.
The Wayside Last Minute Hotel Deals
Concord's Colonial Inn
48 Monument Square Concord MA
Book a stay at this historic hotel in Concord. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
North Bridge Inn
21 Monument Street Concord MA
Book a stay at this business-friendly B&B in Concord. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Monument Square and Sleepy Hollow ...
Bedford Plaza Hotel - Boston
340 Great Road Bedford MA
Stay at this hotel in Bedford. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Burlington Mall and Minute Man National Historical ...
Residence Inn by Marriott Boston Concord
320 Baker Avenue Concord MA
Book a stay at this business-friendly hotel in Concord. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Aloft by Marriott Lexington
727 Marrett Road - A Lexington MA
Book a stay at this business-friendly hotel in Lexington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Element by Marriott Lexington
727 Marrett Road - B Lexington MA
Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Bedford Motel
30 North Road, Rte 4 & 225 Bedford MA
Book a stay at this business-friendly motel in Bedford. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Minute Man National Historical ...
The Westin Waltham-Boston
70 Third Avenue Waltham MA
Book a stay at this business-friendly hotel in Waltham. Enjoy breakfast (surcharge), room service, and a health club. Our guests praise the helpful staff and ...
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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