Sagamore Vacations from $820

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Your Sagamore Vacation

Come and experience this interesting city for yourself with a Sagamore vacation package. Consider spending some time in the neighborhood of Mashpee Neck, which is great for walking and views, and your time here is bound to be unforgettable. Make your trip to Sagamore even more enjoyable by going sightseeing. Massachusetts Maritime Academy, Heritage Museums and Gardens and Sandwich Glass Museum are among the big attractions worth exploring. Don't put off your visit to this city any longer. The ultimate Sagamore vacation is only a few clicks away with Expedia.

The Latest Sagamore vacation packages

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

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,518, price is now $820 per person
$820
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
From the moment I checked in with Natalie, our 4 days were superb! Natalie was so friendly and explained the property and amenities (our first time there). Even though I researched the property, and am originally from close to Boston, it was the 4th of July weekend, and there was Sooo much going on. Head concierge Nathan provided lots of tips about the best places to see certain events. So helpful. Our room was beautiful and well appointed. I miss the days of the shower cap, sewing kit, slippers, robes, etc. and they provided all that. The bed was extremely comfortable and the housekeeping staff wonderful. We go to Boston a few times a year and will be looking forward to returning here. Fabulous location!

Reviewed on Jul 8, 2026

Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
Save 100% on your flight
Price was $2,254, price is now $1,227 per person
$1,227
per person
Aug 20 - Aug 27
found 18 hours ago
Roundtrip flight included
Chicago (CHI) to Provincetown (PVC)
8.2/10 Very Good! (1,007 reviews)
beautiful beach views and lots of great outdoor recreation spaces. It was pouring rain when we arrived so we did not get to use the big heated pool but we wanted to. free coffee in the lobby was a bonus.

Reviewed on Jul 8, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $1,945, price is now $1,160 per person
$1,160
per person
Aug 20 - Aug 27
found 18 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The location couldn’t have been more perfect and despite it being a holiday weekend the parking lot/BNB never felt crowded. Everyone we encountered was lovely and helpful, and the room was a perfect place to take a midday nap or unwind after hours on the beach! We would definitely stay again.

Reviewed on Jul 6, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $5,326, price is now $3,311 per person
$3,311
per person
Aug 12 - Aug 17
found 4 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
10/10 Exceptional! (9 reviews)
I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended. Tim Lawler

Reviewed on Oct 8, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,554, price is now $968 per person
$968
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)

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Sagamore Hotel Deals

Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
$242 nightly
The price is $277 total per night from Jul 19 to Jul 20
$277 total
Jul 19 - Jul 20
Total with taxes and fees
8.6/10 Excellent! (282 reviews)
"Great value and will come bac!"

Reviewed on Jul 9, 2026

Iris Hotel Cape Cod
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
$311 nightly
The price is $355 total per night from Jul 13 to Jul 14
$355 total
Jul 13 - Jul 14
Total with taxes and fees
8.6/10 Excellent! (619 reviews)
"Cumplió las espectativas ! Muy seguro ! Lindo ! Pude llevar mi mascota , espectacular para la familia"

Reviewed on Jul 9, 2026

Margaritaville Resort Cape Cod
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
$458 nightly
The price is $524 total per night from Jul 16 to Jul 17
$524 total
Jul 16 - Jul 17
Total with taxes and fees
7.8/10 Good! (351 reviews)
"Great location"

Reviewed on Jul 9, 2026

Sea Crest Beach Resort
See all 3,920 properties in Sagamore
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.

Find the Best Sagamore Vacation Packages

Sagamore Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Martha's Vineyard Airport (MVY)
Population
3,600
Max Temp Winter
40ºF
Max Temp Summer
70ºF
Top Sights
Old Silver Beach, Sandy Neck Beach and Water Wizz

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Frequently asked questions

How much does a Sagamore vacation package cost?
You can pick up a vacation package to this popular destination from $820 on Expedia. But how much your vacation to Sagamore costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Sagamore?
November, December and January are the best times to look for cheap Sagamore vacation packages. Traveling in less busy months means you can generally find lower prices on flights and hotels.
How many days is enough for Sagamore?
With a well-organized travel plan, you can easily visit the top Sagamore attractions in a few days. But if you want to discover hidden spots or take day trips, think about booking your Sagamore vacation for longer.
How to find the best Sagamore package deals?
Bagging a cheap Sagamore package deal is easy with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Sagamore package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Sagamore vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and accommodations individually. Better still, you can customize your Sagamore getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Sagamore?
Score fantastic discounts by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Sagamore trip.
Does Expedia offer Book Now, Pay Later Sagamore vacation packages?
If you're like us, you love traveling the world but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Sagamore trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.

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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.