5 Enchanting Chappaquiddick Vacation Rentals for Summer

Searching for Chappaquiddick Vacation Rentals for the summer? I’ve got you covered!

Chappaquiddick Island is the perfect location for a secluded getaway. As frequent visitors who have rented vacation homes on Martha’s Vineyard regularly, my family and I have learned what makes for a perfect retreat.

Forget cookie-cutter condos and predictable resorts. Chappaquiddick’s rentals are as individual as the island itself. You’re in the right place to discover the top 5 Chappaquiddick vacation rentals for your trip

Best Chappaquiddick Vacation Rentals

Ready to find your perfect Chappaquiddick summer rental? Let’s do it! After you see all the properties, check out these Chappaquiddick island rental tips so you have all the information you need before making your booking.

a small car ferry called the On Time III carries 3 vehicles across a small body of water. A ferry dock and sandy beach is visible in the distance. This is one of the fun things to do on chappaquiddick

Visit Chappaquiddick Island: Essential Travel Guide (2024)

A family is preparing for a kayaking adventure at a pebbly lakeshore. The picture captures their backs as they look out over the calm water, with one child in pink and the adult in a green vest both holding yellow paddles, ready to embark on their journey with an orange kayak. Kayaks are available at some chappaquiddick vacation rentals

1. Best Chappaquiddick Vacation Rental for Large Family groups (and it’s pet-friendly!)

View Listing: Private Beach, Family Activities & Pet Friendly

🏠 Sleeps 14, 6BR, 5.5BA | 📍Location: North Neck Road | 💸 Price: $$$$

This Chappaquiddick Island rental home is perfect for large families. It’s an expansive property with six bedrooms and five and a half bathrooms, comfortably accommodating up to 14 guests.

Family-friendly amenities include a fully equipped gourmet kitchen for big family meals, lots of outdoor space for kids to play in nature, and a variety of water sports gear, including kayaks and canoes. The 1750 feet of private beach is a safe spot for swimming as it’s free from rip tides.

There’s a fire pit for cozy evening hangouts, outdoor showers, unobstructed sunset and sunrise views and a guest cottage ideal for multi-generational families or friends.

The property provides beach chairs, towels, kids toys, books and games, water sports equipment like kayaks and canoes and there’s even a ping pong table!

As the home is situated on a 5.5-acre peninsula, you’ll have privacy and peace staying here. Direct waterfront and private beach access is another big pro as in high season, beaches all over Martha’s Vineyard can get crowded and parking is limited.

A major benefit is that round trip Steamship Authority ferry reservations are included for Sunday to Sunday rentals booked more than 30 days in advance.

However, the property can be hard to get to – you’ll need an SUV with 4-wheel drive and high clearance. In addition, while its seclusion is a pro for privacy, the remote location means extra effort for trips to the mainland.

This house on Chappaquiddick Island is my pick for large families because of its ample space for comfort, family-oriented amenities and proximity to wildlife and natural surroundings for bonding activities like birdwatching, hiking, and fishing.

🤩 Book This Family and Pet-Friendly Chappaquiddick Vacation Rental

a view of a wooden japanese-style bridge over a pond in the mytoi gardens on chappaquiddick. Exotic and local trees and plants are visible surrounding the pond. Stone steps lead away from the bridge towards the front of the image — Mytoi Japanese Gardens

2. Best Chappaquiddick Vacation Rental with a Hot Tub

View Listing: Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach

🏠 Sleeps 8, 3BR, 3BA | 📍Location: Central Chappaquiddick | 💸 Price: $$$

This Chappaquiddick home is a charming beach house with three bedrooms and three bathrooms, comfortably accommodating up to 8 guests. It’s dog-friendly and child-friendly too, with kayaks, basketball and corn-hole provided.

The highlight is undoubtedly the hot tub, perfect for unwinding after a day of exploration. There are modern conveniences such as central AC, free high-speed WiFi, and a fully stocked kitchen. A classic Martha’s Vineyard outdoor shower is on-site, as well as bicycles and a Peleton bike.

The pros of this property are that it’s well-equipped and has impressive outdoor spaces for dining, playing games and enjoying the hot tub. It’s also a very short drive to East Beach and the Mytoi Japanese Gardens – two of the most popular spots on Chappy.

The detached queen room offers additional privacy, suitable for couples or older family members. Having such a fully-stocked kitchen, complete with a dining area, blender, toaster, and lobster pot is a real benefit on Chappaquiddick as there are no restaurants

However, you will definitely need a car at this rental. Although Chappy is a small island, the home is located in the interior and is not within walking distance of beaches or the ferry to the town of Edgartown

🤩 Book This Chappaquiddick Vacation Rental with a Hot Tub

Two children are swimming underwater in a clear blue pool, with one child in striped swimwear and pink goggles leading the way while the other, in orange floaties and blue goggles, follows. Sunlight dances across the surface, casting ripples of light down into the water.

3. Best Luxury Chappaquiddick Vacation Rental with a Pool

View Listing: Stunning compound steps to Katama Bay, heated pool, dock & amenities

🏠 Sleeps 9, 5BR, 5BA | 📍Location: Katama Bay | 💸 Price: $$$$

A vacation rental with a pool is a rarity on Chappaquiddick, but the appealing features of this luxurious property don’t stop there. You also have an outdoor kitchen, multiple fire pits, pizza oven a swing set, and an expansive yard.

The main house features a chef’s kitchen, a great room, multiple dining areas, and a screened porch. A separate guest cottage offers additional space, and for entertainment, there’s a barn-turned-game room, gym area with a Peloton, row machine and free weights.

Outdoor enthusiasts are well catered for – kayaks, bikes, paddleboards, beach chairs, and grills are provided. For beach adventures, a Jeep with a beach sticker is available for rent, offering easy access to some of the best bay-side and ocean beaches on the Vineyard.

This property stands out on Chappaquiddick Island with its luxurious heated pool. Water views from every level, fine furnishings and luxury finishes make it a perfect choice for travellers looking for a high-end living experience

This is a spacious and well-appointed home in a great location opposite Katama bay (one of my favorite kayaking spots), just a short drive to the chappy ferry for easy access to Edgartown. Another pro is the range of high-end amenities on offer, like kayaks, paddleboards, and Jeep rental.

However, there are a couple of cons. As a luxury chappaquiddick vacation rental, the high-price point may be prohibitive for some. In addition, with a minimum rental age of 32, it may not be suitable for younger groups looking for a vacation in Chappaquiddick.

The exclusive amenities, sophisticated design, and serene location make this property an ideal choice if you’re looking for a luxury rental with a pool on Chappaquiddick

🤩 Book this Luxury Chappaquiddick Vacation Rental

a wooden bridge with a sandy surface and thick wooden rails. water can be seen underneath and on either side — Dike Bridge and East Beach in the distance

4. Best Chappaquiddick Rental Home with Private Beach

View Listing: Chappy cottage with private beach

🏠 Sleeps 9, 4BR, 2BA | 📍Location: Dike Bridge | 💸 Price: $$$

What sets this rental apart is the coveted access to a private beach, just 200 feet from the doorstep. Ideal for families with small children, the calm waters are perfect for safe swimming, kayaking or paddleboarding. It’s also just a short stroll to the Dike Bridge East Beach entrance.

The cottage comfortably sleeps 9 across 4 bedrooms. An eat-in kitchen with an island opens to a cozy first-floor living room, while the upstairs room doubles as a second living space or extra sleeping quarters, complete with a deck and stunning views over Pocha Pond.

Additional amenities include an outdoor shower, BBQ grills, beach chairs, and bicycles.

The property’s prime location, just about 200 feet from a private beach makes it ideal for travelers who prioritize privacy. Another benefit is its proximity to the Japanese-style Mytoi Gardens, just a 4 minute walk away.

However, there are some downsides to this rental home. With only 2 bathrooms (and just one shower) for a house that sleeps 9, there might be some inconvenience, especially for larger groups. One of the bedrooms requires walking through a bathroom to access it, which is not ideal for privacy.

Despite the considerations around layout, this Chappy cottage is an excellent choice for those who want to relax on the sand on their own private beach and swim in safe and calm waters.

🤩 Book this Chappaquiddick House with Private Beach

A serene view of edgartown from Chappaquiddick with a variety of boats moored on calm waters. In the background, grand houses overlook the scene, nestled among lush greenery, under a hazy sky — Vew of Edgartown from the dock on the Chappy side

5. Best Chappaquiddick Rental Without a Car (Walk to Town!)

View Listing: Ocean~Harbor View Chappy Respite yet Walk to Town or Private Beach, SAA Tickets

🏠 Sleeps 8, 4BR, 4BA | 📍Location: Manaca Hill | 💸 Price: $$$

For those who love the tranquility of Chappaquiddick yet wish to stay within walking distance to the action in Edgartown, this ocean-view rental home is the one to choose.

This property was recently remodelled with a new kitchen and bathrooms. Other amenities include an outdoor shower and air conditioning.

Featuring four bedrooms and four bathrooms, it comfortably sleeps eight guests. Just 800 yards from the Chappy ferry dock and a similar distance to a private 3-acre beach, the location is ideal for those who appreciate the best of both worlds.

The charm of this house lies in its ability to offer a secluded retreat without sacrificing accessibility. Its proximity to Edgartown allows guests to easily walk into the heart of downtown (after a short ride on the Chappy ferry).

It’s ideal for those who want to enjoy the restaurants and shops without worrying about the notoriously difficult task of finding parking in Edgartown in the summer!

Other pros include access to a private beach and Steamship Authority reservations are provided for some dates

On the downside, the guests must provide their own bed linens and beach towels although rental services are available. In a large group, it might be inconvenient for everyone to take so many linens and towels.

In addition, the private beach is not directly connected to the home and is a few minutes walk.

🤩 Book this Chappy Rental Close to Town

4 beach huts with blue, red and white striped roofs can be seen in the distance. scrub and sand is in the forwground and a fence and sand dunes are in between — Chappy Beach Club

Chappaquiddick Island Vacation Rental Tips

When planning a rental on Chappaquiddick, there are a few things you should know:

Accessing Chappaquiddick: Chappy is an island-off-an island. To get there, you’ll first need to make your way to Martha’s Vineyard. Once you’re on the main island, the Chappy Ferry, will bring you to Chappaquiddick.
Just one store on the Island: The single store on the island just carries a small number of snack items, drinks and a handful of household items. Make sure to bring all your essentials with you from the mainland – think groceries, personal care items, and any specific necessities.
Transportation Considerations: Having a car on Chappaquiddick is almost a necessity. The island’s attractions and beaches are spread out and there is no public transportation. If you’re renting a property, check if there are any vehicle requirements, especially if you’re planning to explore off-road beaches. Some rentals provide bikes to use during your stay.
Connectivity Concerns: One of the island’s quirks is its varying cell phone signal strength. It can be weak, particularly as you move towards the eastern parts of the island. Ask your host about the cell reception in the area of your rental and check if the property has reliable WiFi.
Embrace Outdoor Living: Prepare to spend a lot of time outdoors. Pack accordingly, with beach gear, comfortable outdoor clothing, and perhaps hiking or biking gear.
Privacy and Quiet: If you’re seeking nightlife, bars and restaurants, Chappaquiddick might not be the best location on Martha’s Vineyard for your stay. It’s more geared towards peaceful, nature-focused vacations.

Things to do while Renting on Chappaquiddick

Now you’ve found your perfect summer rental, time to read my guide to Chappaquiddick activities and plan your vacation! There’s a wide selection of activities available on the island.

Golfers can play a round at the Royal and Ancient Chappaquiddick Links. Visitors can enjoy a cool, shaded retreat from the sun at Mytoi Japaense Gardens. Take a tour out to Cape Poge to see the lighthouse or spend your days hiking the unspoilt trails.

Venture onto the water for kayaking, paddleboarding, fishing and swimming or relax on East Beach or Wasque with a good book.

Final Thoughts: Chappaquiddick Vacation Rentals

That’s a wrap on my guide to the 5 best vacation rentals on Chappaquiddick for the summer. Whether you’re a large family group, seeking luxury amenities, or want a cozy spot near the beach, there’s something for everyone on Chappy.

Chappaquiddick is unique – it’s quiet, close to nature, and a bit off the beaten path. Plan ahead, pack smart and embrace the outdoors to make the most of your trip to the island.

Share your plans and any questions in our Martha’s Vineyard Travel Tips group on Facebook. Happy travels!