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The Wayside Vacation Packages

The Wayside Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sea Mist Resort by VRI Americas

Sea Mist Resort by VRI Americas

3 out of 5
Save 100% on your flight
per person
Mar 15 - Mar 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star business-friendly aparthotel in Mashpee. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Mashpee Commons and Old Indian Meetinghouse are located nearby.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Stay at this 4.5-star luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Boston Common and Fenway Park are located nearby.
Raffles Boston

Raffles Boston

5 out of 5
Save 100% on your flight
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Stay at this 5-star 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 Boston Common and Fenway Park are located nearby.
YOTEL Boston

YOTEL Boston

4 out of 5
Save 100% on your flight
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Stay at this 4-star hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the restaurant and the bar in our reviews. Popular attractions Boston Common and TD Garden are located nearby.
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
per person
Mar 3 - Mar 7
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Save 100% on your flight
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Fenway Park and Boston Common are located nearby.
Holly Tree Resort by VRI Americas

Holly Tree Resort by VRI Americas

3 out of 5
Save 100% on your flight
per person
Mar 15 - Mar 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Cape Cod Inflatable Park and Englewood Beach are located nearby.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Stay at this 5-star 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 TD Garden and Boston Common are located nearby.
Residence Inn Boston Logan Airport/Chelsea

Residence Inn Boston Logan Airport/Chelsea

3.5 out of 5
per person
Mar 3 - Mar 7
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Stay at this 3.5-star business-friendly hotel in Chelsea. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Save 100% on your flight
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fenway Park and Boston Common are located nearby.
Courtyard by Marriott Boston Downtown/North Station

Courtyard by Marriott Boston Downtown/North Station

3 out of 5
Save 100% on your flight
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
per person
Mar 3 - Mar 7
found 1 day ago
Roundtrip flight included
New York (JFK) 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 Boston Common and TD Garden are located nearby.

3-4 Night Vacations in The Wayside

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Boston Logan Airport Chelsea

Hampton Inn Boston Logan Airport Chelsea

2.5 out of 5
per person
Mar 3 - Mar 7
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
SpringHill Suites by Marriott Boston Peabody

SpringHill Suites by Marriott Boston Peabody

3 out of 5
per person
Feb 21 - Feb 24
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Hyatt Place Boston/Medford

Hyatt Place Boston/Medford

3 out of 5
per person
Mar 3 - Mar 7
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Homewood Suites by Hilton Boston-Peabody

Homewood Suites by Hilton Boston-Peabody

3 out of 5
per person
Feb 21 - Feb 24
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)

5-7 Night Vacations in The Wayside

Price found within the past 48 hours. Click for updated prices.
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Boston (BOS)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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
Stay at this 3-star 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
Stay at this 3.5-star business-friendly B&B in Concord. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Monument Square and Sleepy Hollow ...
North Bridge Inn
Residence Inn by Marriott Boston Concord
Residence Inn by Marriott Boston Concord
3 out of 5
320 Baker Avenue, Concord, MA
Stay at this 3-star 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
Aloft Lexington
Aloft 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 Lexington
Element Lexington
Element Lexington
3 out of 5
727 Marrett Road - B, Lexington, MA
Stay at this 3-star business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Element Lexington
Bedford Plaza Hotel - Boston
Bedford Plaza Hotel - Boston
2.5 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 Lexington Battle Green are located ...
Bedford Plaza Hotel - Boston
Embassy Suites by Hilton Boston Waltham
Embassy Suites by Hilton Boston Waltham
3.5 out of 5
550 Winter Street, Waltham, MA
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 ...
Embassy Suites by Hilton Boston Waltham
Hampton Inn & Suites Boston/Waltham
Hampton Inn & Suites Boston/Waltham
2.5 out of 5
135 2nd Ave, Waltham, MA
Book a stay at this business-friendly hotel in Waltham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hampton Inn & Suites Boston/Waltham
See all 583 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.