Brewster Vacation Packages

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Your Brewster Vacation

With one of our vacation packages to Brewster, you'll find endless opportunities for fun and excitement. There's so much to look forward to, including its rich history and rural countryside. Cape Cod Museum of Art, Cape Cod Museum of Natural History and Skaket Beach are just some of the many sights worth checking out during your trip to Brewster. Check out Expedia's extensive range of travel options and start planning your perfect vacation to Brewster now.

Top Brewster Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn PLUS+ Boston - Woburn/ Burlington

Red Roof Inn PLUS+ Boston - Woburn/ Burlington

2.5 out of 5
Price was CA $1,251, price is now CA $882 per person
CA $882
per person
Jun 17 - Jun 21
found 21 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
7.2/10 Good! (1,200 reviews)
I recently stayed at the red roof in Woburn Massachussets with my family, and my experience was great from start to finish. The staff were warm, professional, and attentive, making sure every detail of my stay was good. The room was spotless, and very comfortable, with all the amenities I needed. The facilities were well-maintained, Every interaction felt genuine and welcoming. It truly made me feel at home while still enjoying the hotel stay. the hotel is close to many great restaurants and a shopping center which was super convenient. I recommend this hotel to anyone looking for a seamless, enjoyable. I will definitely return on my next trip.

Reviewed on May 4, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $3,983, price is now CA $2,689 per person
CA $2,689
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!

Reviewed on Sep 20, 2025

Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was CA $1,819, price is now CA $1,233 per person
CA $1,233
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
8.4/10 Very Good! (1,430 reviews)
Nice area, comfy bed, great value.

Reviewed on May 4, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $2,994, price is now CA $2,097 per person
CA $2,097
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (685 reviews)
Sophisticated interior with accents of Cape Cod’s design language.

Reviewed on May 4, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,291, price is now CA $2,306 per person
CA $2,306
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
They're always my hands down favorite in Boston! Thanks for being so lovely!!

Reviewed on May 5, 2026

Brewster Beach Vacation

There's nothing more relaxing than a Brewster vacation. Whether you're enjoying refreshing cocktails at a local bar or reading your favourite magazine by the shore, your trip to Brewster is an ideal time to live out your beachy dreams. Many visitors like to stay near Breakwater Beach, situated just 2 kilometres from downtown. However, you'll also discover a great range of Brewster vacation packages close to Linnell Landing Beach and Robbins Hill Beach, two other well-liked nearby options.

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Brewster Hotel Deals

The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
2907 Main Street Brewster MA
The price is CA $399 per night from May 7 to May 8
CA $399
CA $535 total
May 7 - May 8
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
A Quick stay but the room was large and comfortable and clean an the staff was excellent

Reviewed on Apr 28, 2026

The Mansion at Ocean Edge
The Villages at Ocean Edge

The Villages at Ocean Edge

3.5 out of 5
One Villages Drive Brewster MA
The price is CA $156 per night from May 10 to May 11
CA $156
CA $241 total
May 10 - May 11
includes taxes & fees
The Villages at Ocean Edge
Brewster Green Resort

Brewster Green Resort

3.5 out of 5
203 Lund Farm Way Brewster MA
The price is CA $309 per night from May 21 to May 22
CA $309
CA $353 total
May 21 - May 22
includes taxes & fees
9.4/10 Exceptional! (130 reviews)
Clean but bleach smell was strong for me. Clubhouse doesn’t open until 8 and no coffee in room so tough for us early risers.

Reviewed on Apr 20, 2026

Brewster Green Resort
See all 430 properties in Brewster
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 Brewster

Breakwater Beach

Breakwater Beach

Swim in the clear, shallow waters of this sandy bay and return at low water to explore a sprawling field of fascinating tidal pools.

Breakwater Beach
Cape Cod Museum of Natural History

Cape Cod Museum of Natural History

When the beauty and natural richness of Cape Cod’s landscape leave you craving to know more, enjoy a tour through the halls of this museum and education center.

Cape Cod Museum of Natural History
Sunset on Paine’s creek beach Cape Cod MA USA

Paine's Creek Beach

Why not spend a carefree afternoon at Paine's Creek Beach during your travels in Brewster? Stroll along the seaside in this relaxing area, or check out its seafood restaurants.

Paine's Creek Beach

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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.