My mom and I just returned from our first trip to Martha’s Vineyard, Massachusetts and all I can say is wow. We cannot get over how beautiful and magical the island is, and especially where we stayed. We’ve been to Nantucket, Cape Cod, Newport, and the likes, but Martha’s Vineyard just seemed to be on a whole other level in terms of the natural beauty (the farmland reminded us of the Hamptons), the historic homes (they were immaculately kept with the most insane gardens!), and the unique little towns all over the island, which offered so much diversity and opportunities to explore.

I did this trip with my mom for a little mother/daughter “babymoon,” before my baby girl is due this October, but would say that the island, and the resort where we stayed, The Winnetu, is an ideal getaway for couples and full-blown families too! I dive deeper into just how family-friendly The Winnetu is below.

A quick note on timing– we went from June 23-27, which was just before the island really got crowded for the summer. It was refreshingly uncrowded, which we think was due to a lot of schools still being in session. The weather was delightful (hot and sunny 4/5 days we were there!) so we’d highly recommend this time of year. Though I can only imagine how fun and lively the island is during the rest of the summer weeks, and also how lovely it is in the early autumn and late spring too!

Let’s dive right in to our full Martha’s Vineyard trip recap and recommendations…

Where We Stayed

The Winnetu Oceanside Resort: What a special spot! The Winnetu Resort is one of the three resorts part of the Little Gem Resorts properties, which also include The Nantucket Hotel & Resort in (you guessed it) Nantucket and Lovango Resort & Beach Club in St. John, U.S. Virgin Islands! MV, ACK, and St. John is a pretty epic trio of resort destinations if you ask me. 😂 The Winnetu kindly hosted us for this stay, but all opinions I share are my own.

I should also note that Little Gem Resorts offered a discount code for us as well. I rarely get discount codes for hotels, not to mention five start luxury properties like these, so definitely take advantage while I have this! You can use code LITTLE to receive 10% off all Little Gem Resort property bookings (Lovango, Nantucket, and Martha’s Vineyard) for the rest of 2025 season into 2026.

The Winnetu has been family-owned and operated since 1968, and it shows in the pride and care that encompasses the property. They have a variety of accommodation options, like rooms, suites, and full blown cottages that you can rent. We stayed in the Lilly Pulitzer Summer Cottage and it was even better than you could imagine.

It’s located in a prime spot– steps from the main resort pool, but tucked away by itself at the end of the main property so you have some privacy and serenity. It has two full bathrooms, a primary bedroom with a king sized bed, a second bedroom with two twin beds, and a pull-out sofa in the living room. There’s also a full kitchen, an expansive patio with a dining set and its own hot tub, and a private rooftop with seating that overlooks the lawn and main pool. You could easily fit two-five people in the cottage and have the best time.

But our favorite part of all? All of the special Lilly Pulitzer touches! The Lilly print team was on-site to hand paint and hand-shell every little detail of the cottage, so it’s truly like stepping into a work of art that’s full of Lilly’s signature color and whimsy. We had the best time just hanging out on the back deck, having coffee in the morning with our feet in the hot tub, and of course cooling off in the AC after a day of exploring all around the island. It truly felt like our own little home (and it looked that way too, considering all of the luggage we brought 😂), but with the luxury of a daily cleaning service and all the fabulousness that come with a one-of-a-kind Lilly Pulitzer-designed cottage!

I also received a number of questions regarding whether or not the resort had dog-friendly accommodations, and yes they do!

Throughout our five day, four night stay, we really got to know the property well. There were too many highlights to note, so here’s a list of some of our favorite aspects of the resort!

• It’s the only resort located on the island’s iconic South Beach, and has its own walking path to the beach.
• You can ride bikes into Edgartown or take their complimentary shuttle that drops off in downtown Edgartown (keep reading below for a little breakdown of some of the towns on MV!). During the summer, this shuttle runs hourly during the day and every half hour during the evening.
• Speaking of transportation options, they also have a water taxi (a gorgeous Vineyard Vines-themed boat!) that takes guests by water to/from the resort from Edgartown. We hopped in it one evening and had the most enjoyable cruise through the harbor right after a rain shower, with a big beautiful rainbow guiding our way.
• Two more fun antique transportation options that they have for rides around the island (that we didn’t take advantage of but would be perfect for kids) are their restored 1956 fire truck and open-air, wood paneled 1931 Model A Ford bus!
• The resort property includes two (heated!) pools, a large hot tub (separate from the one we also had on the back deck of our cottage!), tennis courts, pickleball courts, and complimentary yoga and pilates on the front lawn. All of these activities are included (there’s no resort fee!) which we were blown away by.
• Lastly, but something that we were considerably impressed by, was their extensive children’s programming! They have drop-in children’s programs for nearly every age and at every time of day– that are like epic summer camps, located all around the expansive resort property. In addition to those, there are activities and games everywhere you turn. Like foosball, ping-pong, life size chess, a Pirate ship playground, an air-conditioned kids’ playroom, you name it.
• Oh one more note! The resort offers lemonade and cookies in the afternoon and s’mores around the courtyard firepits in the evening. Which you know my pregnant-self thoroughly enjoyed. 😉

Where We Ate

The Dunes: This was The Winnetu’s primary restaurant and a destination worth visiting in itself! We had dinner and breakfast here a number of times throughout our stay, and it over-delivered every time. Some of our major callouts were the cacio e pepe (featuring homemade pasta and truffles flown over from Italy!), the smoked campfire s’mores globe dessert (the presentation is just as fun as it is delicious), and the phenomenal eggs Benedict for breakfast.

We also had their weekly Clambake at The Dunes, which is usually out on their back lawn but was moved indoors due to some potential rain (which was actually really nice because it cooled things down– the heatwave this summer has been no joke! But again maybe it’s because I’m six months pregnant 😂). We reserved lobsters ahead of time and they cracked them on the spot for us. Definitely dabble in the kids’ station at the Clambake for the macaroni too. 😉 There was also a surprise performance from the Vineyard Sound a cappella group… such a fun way to enjoy dinner.

General Store: I thoroughly took advantage of this *adorable* little spot right of the lobby of the resort. They had grab-and-go breakfast and lunch, incredible iced coffee in the morning, and all the provisions you could want– from sunscreen to The Winnetu merch!

Behind the Bookstore: My mom and I enjoyed lunch here our first day exploring Edgartown. It’s quite literally tucked away “behind the bookstore” and had lots of options including refreshing beverages and big salads! They also have a fun bar area that we will definitely be revisiting post-pregnancy.

19 Raw: Our good friend Tim, AKA the concierge at The Winnetu, helped us get into this highly popular restaurant in Edgartown. Btw, Tim was incredibly helpful the whole time we were there. Definitely pay him a visit in his office off the main building and tell him that Amy and Debra say hi!! Anyways, the “side” of shrimp fried rice that I ordered at 19 Raw was literally entrée-sized and probably one of the best things I’ve eaten all summer!

Black Dog Cafe: We spent a lot of our trip exploring the island (my mom had her car!) so when we were visiting the town of Vineyard Haven we decided to grab lunch at the original Black Dog Cafe. I’ve seen so much fanfare around Black Dog over the years, but had never truly experienced it until we visited. In Vineyard Haven, there’s a Black Dog café, bakery, and historic restaurant on the water. It was a great spot to cool off with a drink and lunch, and read about the history of such an iconic Martha’s Vineyard brand.

Morning Glory Farm: A local farmstand and marketplace with wildflowers, freshly baked pies, and beautiful, fresh produce. We would have taken more advantage of it if we cooked anything in our cottage, but had to stop in since it came so highly recommended!

Rosewater Coffee and Espresso Love: Two coffee and bakery spots in Edgartown that we really enjoyed! Great lattes, breakfast sandwiches, and baked goods at both. Rosewater was a little fancier whereas Espresso Love felt more casual and local.

What We Did

Lounge by the Pool: On two of the afternoons that we spent in Martha’s Vineyard, we ended up lounging by the pool at The Winnetu and were so relaxed that Deb fell asleep both times. 😂 Both of their pools are heated (and very warm!) and they had plenty of lounge chairs and seating areas so that even with the resort at near maximum capacity, we still never had any issue finding loungers next to each other.

It also looked like they had a great poolside menu at the main pool (there’s also a casual outdoor restaurant and bar there!) that we never took advantage of food-wise, but did order a number of drinks from that were delicious. The poolside bar had Soggy Dollar Bar Rum (my absolute favorite) from the British Virgin Islands, since one of The Winnetu’s sister properties is The Lovango, located in St. John (btw, my 10% off discount code applies when booking there too! The code is LITTLE).

Pickleball: We had a chance to hit a few pickleballs at The Winnetu’s Activity Center, which you know we always love doing. A few of the little kid campers wanted to play with us too, which was adorable.

Water Taxi to Edgartown: Not only was this a form of helpful transportation, but it was a standout highlight of the trip. We had The Winnetu’s water taxi (a beautiful Vineyard Vines-themed boat!) take us from Edgartown to the resort for their Clambake night, and it was the prettiest 20-minute ride along the harbor. Just book your spot on the water taxi ahead of time with The Winnetu’s concierge, Tim!

Exploring and Shopping: Like I mentioned above, The Winnetu has a complimentary shuttle that you can hop on to get into Edgartown, but my mom had also driven her car from Maine (she took the car ferry out of Woods Hole to get to Martha’s Vineyard) so we had her car to use the whole time as well. I would say that you only really need a car if you want to explore towns other than Edgartown. Other than that, you’re really golden with all of the transportation options that The Winnetu has for getting into Edgartown.

Regarding all of the towns on the island, our favorites (in this order!) were Edgartown, Vineyard Haven, and Oak Bluffs. Edgartown seemed to have the best shopping and dining, and is the most well known of the towns on MV. Vineyard Haven felt even more small town and casual than Edgartown, and Oak Bluffs was definitely the most eccentric! For Edgartown, don’t miss walking down North Water Street (especially at sunset and by the Edgartown Harbor Lighthouse!) and stopping into Nell for shopping. In Vineyard Haven, the original Black Dog Cafe is definitely worth seeing, and for shopping don’t miss The Beach House and Magnetic North! Oak Bluffs didn’t have our favorite shopping but made up for it in its charming architecture– the famous Gingerbread Cottages are absolutely worth visiting.

Ferry to Chappaquiddick: On our last full day on Martha’s Vineyard, we walked on to the five minute ferry over to Chappaquiddick to meet one of my mom’s friends who has a home there. It’s a pretty desolate island– with only a beach club and a few hundred homes (no restaurants or anything), but had so much natural beauty. I wouldn’t necessarily recommend going unless you know someone who lives there or belongs to the beach club, which was really old school and cute!

In all, we couldn’t get over how immediately fast we fell in love with Martha’s Vineyard, and how wonderful staying at The Winnetu made our entire trip. I shared much more via Instagram stories, which I saved to an Instagram highlight that you can see here. We will absolutely be back– and I definitely want to return with baby girl because it was seriously such a family-friendly resort experience. And not to mention SO easy to get to from NYC! I flew from LGA to Martha’s Vineyard and the flight took less than 40 minutes.

I’m listing a few things below that we didn’t get to, but will be at the top of our list for the next time we visit! Fingers crossed that it’s right around the corner…

On Our List for Next Time

• Poolside lunch at The Winnetu’s Poolside Grill— their fresh fruit plate sounded divine!
• Seafood Shanty top deck for the view and cocktails
• Beach day on South Beach (walkable from The Winnetu!)
• The Alchemy for dinner (I’ve heard amazing things about the spa water?!)
• Bad Martha’s for drinks and pizza
• West Tisbury Farmer’s Market! We missed the days it was open!

Don’t Forget….

You can use code LITTLE to receive 10% off all Little Gem Resort property bookings (Lovango, Nantucket, and Martha’s Vineyard) for the rest of 2025 season into 2026. I rarely receive a discount code for travel properties like these, so make your booking while it’s still active! xx