Westborough Vacation Packages 2026 from $256

Westborough flight + hotel vacation packages

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

Porter Square Hotel

Porter Square

Save 100% on your flight

$256

per person

Feb 5 - Feb 8

found 5 hours ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A garden, express check-out, and a computer station are also on offer.

Boston Harbor Hotel

North End

Save 100% on your flight

$939

per person

Feb 12 - Feb 15

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.

Hotel Commonwealth

Fenway–Kenmore

Save 100% on your flight

$1,157

per person

Mar 13 - Mar 20

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

This smoke-free hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the laundry service, conference space, and valet parking. A lobby fireplace, luggage storage, and concierge services are also on offer.

Raffles Boston

Back Bay

Save 100% on your flight

$825

per person

Feb 12 - Feb 15

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.

The Whitney Hotel

Beacon Hill

Save 100% on your flight

$626

per person

Feb 12 - Feb 15

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a garden, and a lobby fireplace are also offered.

Top Westborough hotels deals

DoubleTree by Hilton Hotel Boston - Westborough

5400 Computer Dr Westborough MA

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$109 total

Jan 2 - Jan 3, 2026

Total with taxes and fees

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Extended Stay America Suites Boston Westborough Computer Dr

1800 Computer Dr Westborough MA

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$90 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. A picnic area and a safe deposit box are also provided.

Extended Stay America Suites Boston Westborough Connector Rd

19 Connector Rd Westborough MA

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$90 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Hampton Inn Boston - Westborough

15 Connector Road Westborough MA

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$132 total

Dec 30 - Dec 31

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Extended Stay America Suites Boston Westborough East Main St

180 E Main St Westborough MA

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$96 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

A gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and a safe deposit box are also provided.

Westborough Inn

4 Boardman St Westborough MA

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$111 total

Dec 27 - Dec 28

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-out. A terrace, a picnic area, and concierge services are also on offer.

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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.

Popular places to visit

Westborough Country Club

Enjoy a round of golf in Westborough at Westborough Country Club. Experience the great live music or attend a sporting event in this family-friendly area.

Lake Chauncy Public Beach

Why not spend a lazy afternoon at Lake Chauncy Public Beach during your trip to Westborough? While in this family-friendly area, you can savor the top-notch restaurants.

Frequently asked questions

How much are vacation packages to Westborough?

With offers starting from as little as $256, hotel and flight packages are an ideal way to stretch your vacation budget. Get ready Westborough — here you come!

How long should my Westborough vacation be?

Usually, 3 nights is how long most people spend exploring Westborough. Wondering if that'll be sufficient time to do everything on your to-do list? Stay a few more nights so you don't miss a thing.

Where can I get the best vacation package deals for Westborough?

For the perfect package deal to Westborough, head straight to Travelocity. Take your pick from as many as 400 airlines and 1,000,000 worldwide properties to create the ideal trip — it couldn't be easier than that.

Why should I book my Westborough vacation bundle with Travelocity?

Travel should be about making cherished memories and leaving all your worries behind — which is why we provide you with a professional team of customer service experts on hand around-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our huge range of package deals. So what are you waiting for? There's no time like the present to secure that vacation you've always wanted.

Can I save money on my Westborough car rental if I book it with a hotel or flight?

You most certainly can — combine your car, flight and hotel into a Westborough vacation package and you'll save a tidy sum. With so much to discover in Westborough, having your own ride will come in handy. Once you've settled into the driver's seat, get out on the wide open road and head toward Plymouth Rock, a renowned sight roughly 55 mi from Westborough.

Which airport is best for Westborough?

Logan Intl. Airport (BOS) (30 mi away from downtown), Bradley Intl. Airport (BDL) (60 mi away from central Westborough) and T.F. Green Airport (PVD) (40 mi away from central Westborough) are the top options for Westborough.

What is there to do in Westborough?

While getting off the beaten track is rewarding, you shouldn't miss the well-known sights that make a destination famous. Westborough Country Club and Lake Chauncy Public Beach are a couple of them in Westborough.

Where should I stay when visiting Westborough?

The Hampton Inn Boston - Westborough is the number one choice of many travelers. Book now before it's too late.