West of Town Vacation Packages

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Your West of Town Vacation

Organizing your next break is a cinch with a West of Town vacation package. The neighborhood of Cliff, which is good for coastal beaches, makes a terrific base to uncover the marvels of this vibrant city. If your trip to West of Town includes a little sightseeing, visit major attractions such as Surfside Beach, Jetties Beach and Cisco Beach. Check out Expedia's wide range of travel options and start planning your ideal vacation to West of Town today.

Top West of Town Vacation Deals

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

Eurostars The Boxer

4 out of 5
West End
Price was CA $1,352, price is now CA $882 per person
CA $882
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,426 reviews)
Clean room and good staff. Room is a bit outdated

Reviewed on Apr 15, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $3,971, price is now CA $2,181 per person
CA $2,181
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
The staff were so kind and let us check in early. They constantly asked how we were enjoying the stay and if there was anything that we needed. The property was clean and super cute!

Reviewed on Apr 13, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,112, price is now CA $1,870 per person
CA $1,870
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,007 reviews)
Classic luxury, a true five-star experience. Spectacular Boston Harbor views, top-notch staff, extra-comfortable bedding, rainfall shower.

Reviewed on Apr 12, 2026

Life House, Nantucket

Life House, Nantucket

3.5 out of 5
Nantucket Town
Price was CA $4,613, price is now CA $2,846 per person
CA $2,846
per person
Jun 20 - Jun 27
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (65 reviews)
The Life House was a very quiet, charming and friendly spot. Very much so a boutique hotel feel. The only thing that wasn’t ideal was the room we stayed in on the 3rd floor. Being over 6 feet, the room had slanted ceilings and a very tight doorway. It was very tight and not spacious unlike some of the other rooms I saw. Would definitely stay again but would make sure I don’t stay in that room again.

Reviewed on Sep 26, 2025

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston

5 out of 5
Downtown Boston
Price was CA $4,943, price is now CA $3,257 per person
CA $3,257
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (445 reviews)
Club level is well worth it. The service was wonderful

Reviewed on Apr 16, 2026

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West of Town Hotel Deals

Private Modern Bedroom In a Central Location

Private Modern Bedroom In a Central Location

Nantucket MA
9.2/10 Wonderful! (30 reviews)
Good

Reviewed on Oct 21, 2025

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Private Modern Bedroom In a Central Location
Nantucket - edge of town

Nantucket - edge of town

Nantucket MA
The price is CA $270 per night from Apr 19 to Apr 20
CA $270
CA $692 total
Apr 19 - Apr 20
includes taxes & fees
9.6/10 Exceptional! (88 reviews)
Host was very responsive and helpful. Great location.

Reviewed on Oct 23, 2025

Nantucket - edge of town
Quiet getaway for two

Quiet getaway for two

Nantucket MA
9.6/10 Exceptional! (74 reviews)
Quaint little spot, perfect for a long weekend stay. Host was responsive and helpful.

Reviewed on Sep 1, 2025

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Quiet getaway for two
See all 1,168 properties in West of Town
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in West of Town

Siasconet Beach

Siasconet Beach

If a restful vacation is part of your travel plans, Siasconet Beach might be the perfect place to seek out during your trip to Siasconset.

Siasconet Beach
Nantucket_CiscoBeach_6297949-3

Cisco Beach

If a restful vacation is part of your travel plans, Cisco Beach might be the perfect place to seek out during your trip to Nantucket. Discover the museums in this walkable area, or seek out its biking trails.

Cisco Beach
D3RPKW Wooden steps leading down to Jetties beach, Nantucket Island, MA

Jetties Beach

4/5(1 review)

Why not spend a carefree afternoon at Jetties Beach during your travels in Nantucket?

Jetties Beach

What to do in West of Town

Nantucket Tirade Scavenger Hunt

Nutty Nantucket Scavenger Hunt

CA $40
per adult
Nutty Nantucket Scavenger Hunt
Private Vacation Photoshoot with Photographer in Nantucket

Private Vacation Photoshoot with Photographer in Nantucket

CA $850
per adult
Private Vacation Photoshoot with Photographer in Nantucket
See all activities in West of Town

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.