Luxury Road Trip in New England, USA

Boston, Maine, New Hampshire, Vermont & the Berkshires

Best time to travel

May – Sep

Ideal length

13 nights

Perfect for

Couples

From (incl flights)

€8,649 pp

At a glance

International return flights from Dublin to Boston.
13 days' pre-arranged car rental in a luxury SUV.
13 nights’ accommodation in Boston, Kennebunkport, White Mountains, Green Mountains and the Berkshires.
Discover the Bay State with a privately guided tour of Boston and the Massachusetts Museum of Contemporary Art.
Learn about New England’s thriving agriculture with a private lobster boat tour, oyster farm experience and a privately guided organic farm experience with lunch.

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Introduction

Luxury oozes through the Victorian villages, colourful woodlands and majestic mountains of New England. This is a suggested road trip of incredible scenic journeys and even more amazing destinations. Begin your luxury holiday in New England’s historic hub, Boston. Then, set out on a scenic adventure, making your way along picturesque coastal roads to Maine. Journey to the mountains of New Hampshire and Vermont, which beckon with hiking trails and forest adventures, before ending your trip in the rolling hills of the Berkshires. Throughout your luxury holiday, spend your days on private tours and seafood adventures and your nights in our favourite partner hotels and cosy inns.

View all of our luxury holidays to the USA.

Trip Overview

Depart from Dublin to Boston.

Upon arrival, collect your rental car and drive to your luxury hotel in the heart of Boston. Your home for the next two nights, discover the city’s historic charm and gastronomic delights.

Peel back the historic layers of Boston.

Privately tour the city with a local historian. Stroll through Beacon Hill, Downtown Boston and North End, the districts at the heart of the city’s history. Don your thinking cap as you cross the river to Cambridge where you can explore Harvard University and MIT.

Set out on a coastal drive to Kennebunkport.

Pass salt marshes and tidal creeks as you journey up through New Hampshire and into Maine. Arrive in Kennebunkport for a three night stay at your fantastical woodland getaway. Explore the museums, galleries and beaches of this coastal town.

Get a taste of Maine’s seafood.

During your stay in Kennebunkport, spend an evening on a private lobster boat charter, watching in anticipation as the crew haul their traps. You will also visit one of the state’s finest shellfish farms where you can observe how oysters are raised and try your hand at shucking.

Journey through scenic backroads to the White Mountains.

Take a slight detour through the beautiful lakes district of western Maine before arriving at your luxury New Hampshire resort for a two night stay. Explore the spectacular landscapes of the White Mountains, hiking to hidden waterfalls along the way.

Drive to the Northern Green Mountains.

Take a leisurely road trip through the rolling hills and small farms of Vermont’s northeast kingdom. Arrive at your luxury inn for a two night stay. Visit a local organic farm, meeting locals and getting an in-depth look at their fifth-generation maple sugaring operation.

Head south through the Green Mountains.

Follow the Mad River Valley as you go, stopping en route to visit picturesque Woodstock village. Arrive at your charming inn for a two night stay. Explore the quaint small towns of Vermont, stopping by local business, galleries and artisan food stores.

Set out for the Berkshires.

The bucolic Berkshires are a world away from the bustling cities of the state, perfect for a relaxing two night stay. Enjoy a private tour of the Massachusetts Museum of Contemporary Art. Go beyond the museum and discover the bastion of arts and culture in the area.

Drive to the airport for your flight home.

Drop off your rental car and board your flight home. Arrive in Dublin.

Tailoring your holiday

OROKO Itineraries are created with you in mind and no two are the same. These can be used to help plan your trip - or we can design a completely different itinerary to suit you.

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Accommodation

Where to rest your head

Looking for the best accommodation? We've got the contacts

XV Beacon

XV Beacon reigns over Boston’s historic Beacon Hill neighbourhood. This luxurious boutique hotel combines historic Beaux-Arts charm with modern sophistication.

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Hidden Pond

Surrounded by 60 acres of birch groves and balsam fir, Hidden Pond is a secluded forest retreat in the coastal town of Maine’s Kennebunkport.

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Omni Mount Washington Resort

Tucked into the heart of Bretton Woods and surrounded by panoramic mountain views, the Omni Mount Washington has long been a favourite retreat of presidents, poets and celebrities.

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Pitcher Inn

Hidden within Vermont’s Mad River Valley, the romantic Pitcher Inn embraces the traditional, the fanciful and the unexpected.

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Windham Hill Inn

Windham Hill Inn is housed within a 19th-century farmhouse, tucked away in Vermont’s Green Mountains.

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Stonover Farm

Situated in the beautiful Berkshires, Stonover Farm is a luxury family-owned bed & breakfast.

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What people are saying

I wanted to thank you and your team for arranging such an amazing holiday. It was just what I needed – so well organised, no stress and such an incredible hotel and location. It was all seamless. I look forward to my next trip!!

Jennifer – Val Thorens, 2023