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The Wayside Vacation Packages

The Wayside Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was $1,052, price is now $794 per person
$794
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this beach guesthouse in Dennis Port. Enjoy free WiFi, free parking, and a private beach. Popular attractions Sea Street Beach and Pleasant Road Beach are located nearby.
Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Save 100% on your flight
Price was $1,334, price is now $939 per person
$939
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Dennis. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Mayflower Beach and Scargo Tower are located nearby.
The Lenox Hotel Boston

The Lenox Hotel Boston

4.5 out of 5
Save 100% on your flight
Price was $1,959, price is now $1,431 per person
$1,431
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $3,834, price is now $2,819 per person
$2,819
per person
Oct 13 - Oct 18
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.
The Monty Boston

The Monty Boston

2.5 out of 5
Save 100% on your flight
Price was $2,893, price is now $2,141 per person
$2,141
per person
Oct 29 - Nov 2
found 11 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Beechwood Hotel

Beechwood Hotel

4 out of 5
Save 100% on your flight
Price was $1,164, price is now $862 per person
$862
per person
Oct 22 - Oct 27
found 15 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this luxury hotel in Worcester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions DCU Center and Regatta Point Park are located nearby.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
Price was $1,783, price is now $1,325 per person
$1,325
per person
Oct 19 - Oct 24
found 1 day 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.
Arcadian Hotel

Arcadian Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,203, price is now $898 per person
$898
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Brookline. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
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 $1,943, price is now $1,456 per person
$1,456
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
Price was $2,655, price is now $1,991 per person
$1,991
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Andover Inn

Andover Inn

3.5 out of 5
Price was $1,063, price is now $802 per person
$802
per person
Oct 24 - Oct 31
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this business-friendly hotel in Andover. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Addison Gallery of American Art and Andover Center for History & Culture are located nearby.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Save 100% on your flight
Price was $1,640, price is now $1,237 per person
$1,237
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this beach hotel in Beverly. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Salem Common and Salem Witch Museum are located nearby.

3-4 Night Vacations in The Wayside

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was $1,052, price is now $794 per person
$794
per person
Oct 22 - Oct 26
found 1 day 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 $2,495, price is now $1,707 per person
$1,707
per person
Oct 22 - Oct 25
found 1 day 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 $2,158, price is now $1,622 per person
$1,622
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Monty Boston

The Monty Boston

2.5 out of 5
Downtown Boston
Save 100% on your flight
Price was $2,299, price is now $1,739 per person
$1,739
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)

5-7 Night Vacations in The Wayside

Price found within the past 48 hours. Click for updated prices.
The Cape Club Resort

The Cape Club Resort

2 out of 5
Save 100% on your flight
Price was $922, price is now $667 per person
$667
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Save 100% on your flight
Price was $1,255, price is now $847 per person
$847
per person
Oct 16 - Oct 21
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Save 100% on your flight
Price was $1,334, price is now $939 per person
$939
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
Save 100% on your flight
Price was $2,338, price is now $1,668 per person
$1,668
per person
Oct 16 - Oct 21
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)

The Wayside Last Minute Hotel Deals

Concord's Colonial Inn

Concord's Colonial Inn

3 out of 5
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 ...
Concord's Colonial Inn
North Bridge Inn

North Bridge Inn

3.5 out of 5
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 Sleepy Hollow Cemetery and Concord ...
North Bridge Inn
Bedford Plaza Hotel - Boston

Bedford Plaza Hotel - Boston

3 out of 5
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 ...
Bedford Plaza Hotel - Boston
Aloft by Marriott Lexington

Aloft by Marriott Lexington

3 out of 5
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 ...
Aloft by Marriott Lexington
Residence Inn by Marriott Boston Concord

Residence Inn by Marriott Boston Concord

3 out of 5
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 ...
Residence Inn by Marriott Boston Concord
Element by Marriott Lexington

Element by Marriott Lexington

3 out of 5
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 ...
Element by Marriott Lexington
Bedford Motel

Bedford Motel

2.5 out of 5
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 ...
Bedford Motel
The Westin Waltham-Boston

The Westin Waltham-Boston

4 out of 5
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 ...
The Westin Waltham-Boston
See all 588 properties in The Wayside
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.