There is so much to consider when traveling to Martha’s Vineyard - an island with six distinct towns and limited real estate availability. So where should you even get started? In this post we will walk you through five big questions to help you figure out where to stay, then outline our personal recommendations for rental homes, hotels and more.

First, answer these questions:

1. How many people are you traveling with? For how long? 👨‍👩‍👧

   • A lot and for a long time - If you’re traveling with more than 4 people, or want the ability to use a kitchen - you’ll want to rent a house. If you’re traveling for longer than 4 days a house rental is also your best bet.

   • Just a few, for a short trip - If you’re traveling with fewer than 4 people, or for fewer than 4 days, a hotel is a great option!

2. Are you bringing a car? 🚗

   • Should I? If you haven’t already made a car reservation for the summer by March, you’re likely going to have a hard time getting a spot to bring a car over to the island. You can always consider renting a car once you get here, but both options will be pricey.

   • Not planning on it - If you don’t have a car, there are busses and alternate ways to get around. But if you’re staying for more than 2 days, you’ll want to explore all the various towns have to offer! If you’re not bringing a car, we suggest staying in downtown Edgartown or Oak Bluffs because there’s enough restaurants, attractions and beaches within walking distance.

   • Yes! If you ARE bringing a car, you have more flexibility to stay in a hotel or rental home outside of town.

3. What time of year are you coming? ☀️

   • Summer - If you’re coming in summer (Think Memorial Day though Columbus Day weekend) prices will be escalated.

   • Spring, Fall or Winter - If you’re looking for better value, consider coming in the “off season” - we promise you’ll still have a great experience!

4. What is your budget? 💸

   • Unlimited - Skip this question then, and have a drink for us!

   • Conservative - One way to ensure you get the best value is coming to visit at a non-traditional time of year!

   • Tight - If you’re really on a tight budget - check out the campground or hostel for availability! Neither are in-town so you’ll want to bring a bike along or utilize the public bus.

5. What type of experience are you looking for? 🍺

   1. Beachy: Do you want to be in walking distance from a beach?

      • We suggest staying down-island (Edgartown or Oak Bluffs)

   2. Naturey: Do you want to hike trails? Bike ride?

      • We suggest staying up-island (West Tisbury, Aquinnah, Chilmark)

   3. Party: Do you want lots of bars and late night activity?

      • We suggest staying down-island (Edgartown or Oak Bluffs)

   4. Downtown Explorer: Are you excited for bars, restaurants and a little history?

      • We suggest staying in Vineyard Haven, Edgartown or Oak Bluffs for this

Hotel Options 🏨

We have stayed at a lot of hotels over the years! Many Vineyard hotels change management year to year, but we have consistently had great experiences and would personally recommend the following options:

• Edgartown Upscale: Kelley House, HarborView Hotel, any of the Lark Hotels

• Edgartown Budget: Edgar Hotel, Edgartown Commons

• Oak Bluffs Upscale: Summercamp

• Oak Bluffs Budget: Dockside Inn, Inkwell Beach House

• Vineyard Haven: Nobnocket

• Vineyard Haven Budget: Mansion House

• Up Island: Outermost Inn

Rental Home Options 🏠

While you can definitely check out Airbnb or VRBO, there are a few local rental agencies that might have even more options available. We polled our readers and multiple of them had good experiences renting from the following agencies:

• Point B Realty

• Tea Lane

• Sand Castle

• Martha’s Vineyard Vacation Rentals

Camping / Hostel ⛺

There’s a few unconventional options as well - the campground and hostel are a bit outside of town but accessible by bus or bike.

• Marthas Vineyard Campground

• HI Martha’s Vineyard Hostel

Whatever you choose we hope you have an unbelievable experience! If you want a specific question about where to stay, feel free to fill out our form here and we will get back to you!

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