Chappaquiddick Island Pet-friendly Vacations

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Top Pet-friendly vacation packages in Chappaquiddick Island

Price found within the past 48 hours. Click for updated prices.
Doubletree by Hilton Cape Cod - Hyannis

Doubletree by Hilton Cape Cod - Hyannis

$1,018
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Hyannis (HYA)
8.4/10 Very Good! (932 reviews)
The property is simply tired and not up to the Hilton standard. Squeaky beds, smoke alarm that goes off in the room after every shower, feable attempt at a floor unit AC in the hallway. Staff was very friendly. Not their fault.

Reviewed on Aug 11, 2026

Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

$1,485
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
New York (NYC) 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

$2,359
per person
Oct 9 - Oct 14
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
Faraway Martha's Vineyard

Faraway Martha's Vineyard

$2,315
per person
Oct 9 - Oct 14
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

$1,914
per person
Oct 9 - Oct 14
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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

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5* Pet-friendly vacations in Chappaquiddick Island

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

Wequassett Resort and Golf Club

$1,485
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
New York (NYC) 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

$2,359
per person
Oct 9 - Oct 14
found 18 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
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3 Night Pet-friendly vacations in Chappaquiddick Island

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

Margaritaville Resort Cape Cod

$1,063
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
New York (NYC) 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

$1,485
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
New York (NYC) 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

$1,726
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
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4 Night Pet-friendly vacations in Chappaquiddick Island

Price found within the past 48 hours. Click for updated prices.
Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

$1,071
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Hyannis (HYA)
9.4/10 Exceptional! (1,006 reviews)
The Christopher, The Edgartown Collection

The Christopher, The Edgartown Collection

$1,958
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Vineyard Haven (MVY)
9.8/10 Exceptional! (268 reviews)
The Christopher is officially my new favorite hotel. Bailey greeted us when we arrived and was the primary person we saw during our stay. She was lovely and so helpful. I could have fainted when she offered to have our super heavy luggage taken up 3 flights of stairs for us! We were upgraded free of charge to a larger room that had its own private deck. The room was beautiful - gorgeous furnishings and so clean and comfortable. There are homemade, sinfully delicious chocolate chip cookies served at 3 pm - we actually raced back to the hotel for these; they were so good! And the homemade breakfasts served each morning with delicious, strong coffee were a welcome way to start the day. I've already started planning a girls' trip to the island and The Christopher is where we'll stay!

Reviewed on Aug 3, 2026

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

$1,462
per person
Oct 1 - Oct 5
just found
Roundtrip non-stop flight included
Baltimore (BWI) 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

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See all available trips from Columbus to Chappaquiddick Island
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Top Pet-friendly Chappaquiddick Island Hotels

BEST OF CHAPPY SPECTAC WATERWV OCT 12-17 & 2027 WALK-BEACH KAYAK/BIKES FERRY TIX

BEST OF CHAPPY SPECTAC WATERWV OCT 12-17 & 2027 WALK-BEACH KAYAK/BIKES FERRY TIX

Edgartown MA
  • 27 min walk from Chappaquidick Dike Bridge
Book a stay at this beach vacation home in Edgartown. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Wasque Beach and Norton Point Beach ...
9.6/10 Exceptional! (42 reviews)
"We had a great stay at this vacation rental on Chappaquiddick Island. The kitchen was well stocked and the view out the back porch of the bay is gorgeous. We purchased an over the sand vehicle pass and had a great time driving our vehicle on the beach to the lighthouse. Access to the big island, ..."

Reviewed on Jul 28, 2026

BEST OF CHAPPY SPECTAC WATERWV OCT 12-17 & 2027 WALK-BEACH KAYAK/BIKES FERRY TIX
Sleeps 12, amazing view, tennis court, basketball court, beaches

Sleeps 12, amazing view, tennis court, basketball court, beaches

Edgartown MA
  • 4 min drive from Chappaquidick Dike Bridge
Book a stay at this family-friendly vacation home in Edgartown. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Mytoi Garden and Edgartown ...
9.6/10 Exceptional! (41 reviews)
"Great property for extended family vacation. Lots of space and different areas for everyone. However the view wasn’t what it was made out to be as tree growth and foliage now block it; but I bet it was amazing. Some maintenance issues as well. 3 ac heads were not working, 1 toilet was running fairly ..."

Reviewed on Jul 18, 2026

Sleeps 12, amazing view, tennis court, basketball court, beaches
Pristine Chappy! August 29 through Labor Day 2026 Available !

Pristine Chappy! August 29 through Labor Day 2026 Available !

Chappaquiddick Island, Edgartown MA
  • 4 min drive from Chappaquidick Dike Bridge
Stay at this vacation home in Edgartown. Enjoy a garden, laundry facilities, and patios. Popular attractions Mytoi Garden and Edgartown Lighthouse are located ...
10/10 Exceptional! (24 reviews)
"Great stay. E loved Chappy and the house. Biggest problem was getting reservations with Steamship Authority."

Reviewed on Aug 23, 2025

Pristine Chappy! August 29 through Labor Day 2026 Available !
See all 3,392 properties in Chappaquiddick Island
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.

Things to do

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

$50
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
All New Shared Jaws tour Budget Friendly

All New Shared Jaws tour Budget Friendly

$130
per adult
All New Shared Jaws tour Budget Friendly
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50
per traveler
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.