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

$1,073
per person
Sep 12 - Sep 15
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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

Faraway Martha's Vineyard

Faraway Martha's Vineyard

$1,498
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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

Harbor View Hotel

Harbor View Hotel

$1,985
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

$1,434
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Hyannis (HYA)
8.6/10 Excellent! (664 reviews)
Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

$2,183
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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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5* Pet-friendly vacations in Chappaquiddick Island

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

Harbor View Hotel

$1,985
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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

Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

$2,183
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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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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

$576
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)
Faraway Martha's Vineyard

Faraway Martha's Vineyard

$1,685
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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

Harbor View Hotel

Harbor View Hotel

$1,738
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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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4 Night Pet-friendly vacations in Chappaquiddick Island

Price found within the past 48 hours. Click for updated prices.
Courtyard Resort

Courtyard Resort

$517
per person
Oct 4 - Oct 8
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Hyannis (HYA)
8.6/10 Excellent! (106 reviews)
The ac in the room didn't work

Reviewed on Aug 11, 2026

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

$758
per person
Oct 4 - Oct 8
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Hyannis (HYA)
8.6/10 Excellent! (664 reviews)
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

$1,141
per person
Sep 12 - Sep 16
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
9/10 Wonderful! (715 reviews)
This is my second time staying at VHM. I was attending a conference and the location was great. The motel is just a few blocks around the corner from the Vineyard Haven ferry which makes it so convenient for travel. The rooms appear to have been remodeled since last year’s stay, which was a nice surprise. The gentleman who sits at the front desk is always warm and welcoming. The bus stops outside the motel and there are a lot of shops across the street. There is a private beach in the back which I unfortunately didn’t get a chance to enjoy this year. I do plan to stay again next year!

Reviewed on Aug 12, 2026

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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
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
 New Budget Friendly Shared 4 hour African American Heritage Tour

New Budget Friendly Shared 4 hour African American Heritage Tour

$130
per adult
New Budget Friendly Shared 4 hour African American Heritage Tour
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.