Chappaquiddick Island Golf Vacations

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Flight and Golf hotel deals in Chappaquiddick Island

Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

CA $1,047
per person
Oct 15 - Oct 18
found 11 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Hyannis (HYA)
8.6/10 Excellent! (664 reviews)
I thought I had already reviewed this, Holiday was great except for the Friday and Saturday where kids in Baseball uniforms roamed the placed with no disipline from their parents handed out, they knocked our door several times on the Friday night, when we reported it to recption they said they would send security, I seen no security and it didnt stop. The Saturday they were particularly rude at the pool and SAaturday evening they roamed the common area outside like wild Animals, wrecking the communal games and breaking several of them, no point in complaining and I did when checking out and was greeted with so sorry to hear that, we never sat out in that area again and wouldnt let our kids around it as I felt it wasnt well looked after by security. This was very dissapointing and considering we spent 9 days there I would've expected an offer some compensation beacause of these two days. As I said pool staff and a chef in food truck could not have been anymore polite or helpful. I would have to think twice about staying here again. We are from Northern Ireland and in the last 9 years we have been in Cape Cod 3 times so we do throw a lot of expense into travelling to this area from home and we do expect and want to stay in the best possible places within our budget, sadly this time these two days let us down badly. Thanks AJ Watson

Reviewed on Aug 14, 2026

Faraway Martha's Vineyard

Faraway Martha's Vineyard

CA $1,661
per person
Sep 28 - Oct 2
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
We LOVED our stay at Faraway - the pool was amazing, staff was super helpful. They had a very convenient messaging system for requests. The staff recommended the Pelican Club for dinner, which is basically right on-site, but we tried to get in multiple times and there was always a wait! The food at their snack bar was really good for lunch. The location was incredible - it was our first time in Martha's Vineyard and we feel we got so spoiled!!

Reviewed on Aug 11, 2026

Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

CA $1,848
per person
Oct 15 - Oct 18
found 11 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Hyannis (HYA)
9.4/10 Exceptional! (265 reviews)
Our stay at Wequassett Resort and Golf Club was nothing short of extraordinary. From the moment we arrived, we were surrounded by beauty, elegance, and exceptional hospitality. Our Premier Waterview Cottage was absolutely breathtaking. The accommodations were beautiful, luxurious, and exceeded our expectations in every way. Waking up to the stunning waterfront views made our stay even more special. The dining was equally impressive. Every meal was delicious, beautifully prepared, and a true reflection of the quality and care that went into every aspect of our experience. What truly set Wequassett apart, however, was the incredible staff. Each person we encountered went above and beyond to make our 30th anniversary celebration feel truly special. Their genuine warmth, thoughtfulness, and attention to every detail made us feel incredibly welcomed and cared for. Celebrating 30 years of marriage at such a beautiful and extraordinary resort was a memory we will treasure forever. Wequassett gave us far more than a wonderful vacation—it gave us an unforgettable celebration filled with beautiful moments, exceptional service, and memories we will cherish for years to come. We cannot thank the entire Wequassett team enough and are already looking forward to returning. Absolutely beautiful, breathtaking, and truly unforgettable!

Reviewed on Aug 8, 2026

Harbor View Hotel

Harbor View Hotel

CA $2,988
per person
Sep 28 - Oct 2
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
We had an amazing stay and we can not wait to be back.

Reviewed on Jul 31, 2026

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5* Golf holidays in Chappaquiddick Island

Price found within the past 48 hours. Click for updated prices.
Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

CA $1,848
per person
Oct 15 - Oct 18
found 11 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Hyannis (HYA)
9.4/10 Exceptional! (265 reviews)
Our stay at Wequassett Resort and Golf Club was nothing short of extraordinary. From the moment we arrived, we were surrounded by beauty, elegance, and exceptional hospitality. Our Premier Waterview Cottage was absolutely breathtaking. The accommodations were beautiful, luxurious, and exceeded our expectations in every way. Waking up to the stunning waterfront views made our stay even more special. The dining was equally impressive. Every meal was delicious, beautifully prepared, and a true reflection of the quality and care that went into every aspect of our experience. What truly set Wequassett apart, however, was the incredible staff. Each person we encountered went above and beyond to make our 30th anniversary celebration feel truly special. Their genuine warmth, thoughtfulness, and attention to every detail made us feel incredibly welcomed and cared for. Celebrating 30 years of marriage at such a beautiful and extraordinary resort was a memory we will treasure forever. Wequassett gave us far more than a wonderful vacation—it gave us an unforgettable celebration filled with beautiful moments, exceptional service, and memories we will cherish for years to come. We cannot thank the entire Wequassett team enough and are already looking forward to returning. Absolutely beautiful, breathtaking, and truly unforgettable!

Reviewed on Aug 8, 2026

Harbor View Hotel

Harbor View Hotel

CA $2,988
per person
Sep 28 - Oct 2
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
We had an amazing stay and we can not wait to be back.

Reviewed on Jul 31, 2026

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3 Night Golf holidays in Chappaquiddick Island

Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

CA $1,047
per person
Oct 15 - Oct 18
found 11 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Hyannis (HYA)
8.6/10 Excellent! (664 reviews)
I thought I had already reviewed this, Holiday was great except for the Friday and Saturday where kids in Baseball uniforms roamed the placed with no disipline from their parents handed out, they knocked our door several times on the Friday night, when we reported it to recption they said they would send security, I seen no security and it didnt stop. The Saturday they were particularly rude at the pool and SAaturday evening they roamed the common area outside like wild Animals, wrecking the communal games and breaking several of them, no point in complaining and I did when checking out and was greeted with so sorry to hear that, we never sat out in that area again and wouldnt let our kids around it as I felt it wasnt well looked after by security. This was very dissapointing and considering we spent 9 days there I would've expected an offer some compensation beacause of these two days. As I said pool staff and a chef in food truck could not have been anymore polite or helpful. I would have to think twice about staying here again. We are from Northern Ireland and in the last 9 years we have been in Cape Cod 3 times so we do throw a lot of expense into travelling to this area from home and we do expect and want to stay in the best possible places within our budget, sadly this time these two days let us down badly. Thanks AJ Watson

Reviewed on Aug 14, 2026

Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

CA $1,848
per person
Oct 15 - Oct 18
found 11 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Hyannis (HYA)
9.4/10 Exceptional! (265 reviews)
Our stay at Wequassett Resort and Golf Club was nothing short of extraordinary. From the moment we arrived, we were surrounded by beauty, elegance, and exceptional hospitality. Our Premier Waterview Cottage was absolutely breathtaking. The accommodations were beautiful, luxurious, and exceeded our expectations in every way. Waking up to the stunning waterfront views made our stay even more special. The dining was equally impressive. Every meal was delicious, beautifully prepared, and a true reflection of the quality and care that went into every aspect of our experience. What truly set Wequassett apart, however, was the incredible staff. Each person we encountered went above and beyond to make our 30th anniversary celebration feel truly special. Their genuine warmth, thoughtfulness, and attention to every detail made us feel incredibly welcomed and cared for. Celebrating 30 years of marriage at such a beautiful and extraordinary resort was a memory we will treasure forever. Wequassett gave us far more than a wonderful vacation—it gave us an unforgettable celebration filled with beautiful moments, exceptional service, and memories we will cherish for years to come. We cannot thank the entire Wequassett team enough and are already looking forward to returning. Absolutely beautiful, breathtaking, and truly unforgettable!

Reviewed on Aug 8, 2026

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4 Night Golf holidays in Chappaquiddick Island

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

Morgan Hotel

CA $1,336
per person
Sep 28 - Oct 2
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Vineyard Haven (MVY)
8.6/10 Excellent! (248 reviews)
Faraway Martha's Vineyard

Faraway Martha's Vineyard

CA $1,661
per person
Sep 28 - Oct 2
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
We LOVED our stay at Faraway - the pool was amazing, staff was super helpful. They had a very convenient messaging system for requests. The staff recommended the Pelican Club for dinner, which is basically right on-site, but we tried to get in multiple times and there was always a wait! The food at their snack bar was really good for lunch. The location was incredible - it was our first time in Martha's Vineyard and we feel we got so spoiled!!

Reviewed on Aug 11, 2026

The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

CA $1,526
per person
Sep 28 - Oct 2
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Vineyard Haven (MVY)
9.2/10 Wonderful! (199 reviews)
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Discover the ultimate golf vacation from Chappaquiddick Island with Expedia

What are some benefits when booking golf vacations from Chappaquiddick Island?

Booking a golf vacation means putting golf at the centre of your entire experience. Not only will you be able to enjoy easy access to the greens, but you'll often have access to all the equipment you need as well. Plus, golf stays tend to be on the more luxurious end of the spectrum, so you're likely to have some other high-end amenities as well.

How can I find the best golf vacations in Chappaquiddick Island?

The best way to find golf vacations in Chappaquiddick Island is to take advantage of numerous search filters. You can look for golf stays specifically, with additional filters available for certain courses in some destinations. Plus, if you travel during the off-season in , you may even be able to get high-end stays at a discount.

Are there cheap golf packages available?

Yes, you'll find prices as low as CA $1,047, but the overall price depends on several factors. The time of year you travel to Chappaquiddick Island and the amenities you opt for can play a role in the cost of your package. Some package deals offer discounts of up to 16, but that's just a general trend rather than a guarantee.

Can I book golf and spa vacation packages?

Golf is often considered a luxury activity, so it's only natural that it be paired with other high-end experiences. You can implement the spa filter to sort for properties that have spa facilities, which can be especially useful for resting and rejuvenating in between games.

How can I find luxury golf vacations in Chappaquiddick Island?

A lot of golf vacations are already luxurious given the nature of the game, but there are a few things you can do to push it as far as it can go. Use search filters to highlight only 5-star properties to ensure you're getting the best of the best. Business-class flights are available as well in most cases.

Can I book an all-inclusive golf vacation in Chappaquiddick Island?

In many cases, yes. There's even a search filter for all-inclusivity, so you can sort for all-inclusive stays specifically. Even when an all-inclusive experience that matches your needs isn't available, you may be able to find some half-board options. This is also one of the best ways to find luxury golf vacations.

Why should I book golf packages including flights?

When you book your flight and your accommodations together, you can enjoy some serious savings compared to what you'd find booking separately. We're your one-stop shop for all your travel needs, and convenience is just the beginning when booking golf vacations from Chappaquiddick Island with us.

Should I book a last-minute golf vacation?

Booking last-minute to Chappaquiddick Island shouldn't be your first choice, but if you like to travel spontaneously, there are a few benefits to enjoy. Occasionally, you may be able to save money by booking last-minute, as accommodations are interested in filling their last few vacancies as fast as they can. The deals aren't guaranteed, however, so keep that in mind when planning. Sometimes, accommodations will simply be sold out.

Can I book a golf vacation that is fully refundable?

Yes, you'll find several options that are fully refundable among our packages in Chappaquiddick Island. You can even filter for fully refundable stays specifically. Just remember to check out each accommodation's policy specifically to make sure your booking qualifies.

Why should I book my golf trip with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel needs. You can search through a massive collection of packages and potentially unlock discounts by booking your flight and accommodations together. Even more discounts may be available for Expedia Rewards members, such as special deals and the ability to earn points to put toward discounts on future bookings.

Things to do

Martha's Vineyard Self-Driving Audio Tour

Martha's Vineyard: Self-Guided Driving Audio Tour

CA $21
per traveller
Martha's Vineyard: Self-Guided Driving Audio Tour
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

CA $70
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

CA $71
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Chappaquiddick Island

More vacations you might like

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