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The Wayside Vacation Packages

The Wayside Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

3 out of 5
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free bicycles on site, a 24-hour front desk, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
per person
Dec 29 - Jan 3
found 4 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) to Boston (BOS)
Stay at this 4-star boutique hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Burlington Mall and Lexington Battle Green are located nearby.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
per person
Dec 29 - Jan 3
found 4 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) 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 Encore Boston Harbor and TD Garden are located nearby.
Holiday Inn Boston Bunker Hill Area, an IHG Hotel

Holiday Inn Boston Bunker Hill Area, an IHG Hotel

3 out of 5
per person
Dec 29 - Jan 3
found 4 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Somerville. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
per person
Dec 29 - Jan 3
found 4 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Brookline. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Fenway Park and Harvard Square are located nearby.
Harbourtown Suites

Harbourtown Suites

4 out of 5
per person
Dec 29 - Jan 3
found 4 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) to Boston (BOS)
Stay at this 4-star hotel in Plymouth. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Plymouth Rock and Plymouth Harbor are located nearby.
Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

3 out of 5
per person
Dec 29 - Jan 3
found 4 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) to Boston (BOS)
Book a stay at this business-friendly hotel in Plymouth. Enjoy free parking, free water park access, and a 24-hour fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Plymouth Rock and Plymouth Harbor are located nearby.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Save 100% on your flight
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Book a stay at this eco-certified 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 Copley Square and Boston Common are located nearby.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Save 100% on your flight
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free breakfast, free WiFi, and a marina. Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
Save 100% on your flight
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Stay at this 4.5-star luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New England Aquarium and TD Garden are located nearby.
Hampton Inn Boston Seaport District

Hampton Inn Boston Seaport District

3 out of 5
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Boston. 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 New England Aquarium and Faneuil Hall Marketplace are located nearby.

3-4 Night Vacations in The Wayside

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

Boston Lodge and Suites

4 out of 5
Dorchester
per person
Jan 14 - Jan 17
found 10 hours ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
per person
Jan 14 - Jan 17
found 10 hours ago
Roundtrip flight included
Los Angeles (LAX) 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
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Boston (BOS)

5-7 Night Vacations in The Wayside

Price found within the past 48 hours. Click for updated prices.
The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
per person
Dec 29 - Jan 3
found 4 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Dec 29 - Jan 3
found 4 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) to Boston (BOS)
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
per person
Dec 29 - Jan 3
found 4 hours ago
Roundtrip non-stop flight included
Sacramento (SMF) 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
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 a 24-hour fitness center. Our guests praise the helpful staff and ...
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
HYATT house Boston/Waltham
HYATT house Boston/Waltham
3 out of 5
54 4th Ave, Waltham, MA
Stay at this 3-star hotel in Waltham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
HYATT house Boston/Waltham
See all 562 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.

Book the perfect getaway to The Wayside

With Hotwire, booking your next trip to Boston is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to The Wayside while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar The Wayside flight and hotel package for as low as $470.

Living it up in Boston means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s The Wayside, Boston vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in The Wayside for some of the best accommodations and flight deals.

FAQs about cheap The Wayside packages:

How to get cheap vacation deals to The Wayside?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $75.

How much are The Wayside packages?

Vacation packages to The Wayside vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $470.

How to find cheap car rentals near The Wayside?

Hotwire partners with some of the most reliable car rental companies in Boston to bring you the best car rental deals in The Wayside for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to The Wayside now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to The Wayside right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.