Flying into Boston, the gateway of New England, there are a multitude of self-drive routes to take depending on whether it’s an active, beach, mountain or city holiday or a combination of all.

There really is something for everyone on New England holidays.

With varying landscapes and highlights in each state, we recommend you pick and choose depending on your interests, to help we’ve highlighted the best of each state below.

A popular time to visit the region is the famous fall foliage period starting from mid-September in Maine, New Hampshire and Vermont and occurring until mid-October in Massachusetts, Rhode Island and Connecticut (dates vary seasonally).

Summer is also a great time and one of our favourites for enjoying the beaches of Cape Cod, Nantucket and Martha's Vineyard.

Holidays to New England can also be taken in the winters when magical Boston and the mountains of Vermont are the perfect hideaways. 

All of our holidays are tailor-made to your requirements by an expert Travel Specialist
The Inspiring Travel Company Team
01244 433 057

Where to go in New England

Total results: 36
Sort by:
Classic New England Self-Drive
Self-Drive

Classic New England Self-Drive

USA
New England
Boston
+2 others
14 nights from £4,495 per person
Itinerary Highlights
  • Board Lulu, a traditional lobster boat for a two-hour tour of Bar Harbor for a lobster fishing and seal watching experience
  • Take a scenic train ride to the summit of Mount Washington on the world's first mountain-climbing cog railway
  • Take a tour through Ben and Jerry's Ice Cream Factory in Waterberry, indulge in your favourite flavours and take a walk through the Flavor Graveyard to pay your respects to the flavours of past years
  • Wander through the grounds and rooms of Newport Mansions, former summer homes of the Astors and Vanderbilts
Harborside Hotel, Spa & Marina
Hotel

Harborside Hotel, Spa & Marina

USA
New England
Maine Coast (Maine)

With its beach club, boat tours, onsite gym and tennis courts, two swimming pools and spa, the award-winning Harborside Hotel, Spa & Marina leaves no stone left unturned. This is a top resort full of facilities in Frenchman's Bay, Maine. The hotel itself looks the part from the outside, a cross between a wood-clad ski chalet, upmarket beach club and archetypal beach retreat in one. The grounds are...

Camden Harbor Inn
Hotel

Camden Harbor Inn

USA
New England
Maine Coast (Maine)

Camden Harbor Inn is an elegant Relais & Chateaux property set in a desirable Camden location, a delightful waterfront town in the US state of Maine. This heritage hotel dates back to the late 1800s when it served as a summer hideout for well-heeled visitors to New England, and while today it continues this tradition, it’s now also open year-round for all seasons. The distinctive white exterior wi...

Wheatleigh
Hotel

Wheatleigh

USA
New England
Lenox & The Berkshires (Massachusetts)

Wheatleigh is an exceptional Berkshire hotel, the winner of multiple awards for its rooms, service standards and fine dining cuisine. Surrounded by mountains and acres of private landscaped gardens, forests and lawns, the scene is truly set for a regal stay in this stunning 19th-century mansion complete with Romanesque pillars, stone balconies and just 19 exclusive guestrooms. While here you can’t...

Ocean House Rhode Island
Hotel

Ocean House Rhode Island

USA
New England
Newport (Rhode Island)

Believe it or not, Ocean House has been a popular Rhode Island hotel in Watch Hill since the mid-18th century, having first opened its doors to the great and the good in 1868. Thankfully, this enticing heritage can be seen throughout the property, its original architecture and structure beautifully preserved: from semi-open-air terraces lined with stone pillars to a steep tiled roof typical of the...

The Chanler at Cliff Walk
Hotel

The Chanler at Cliff Walk

USA
New England
Newport (Rhode Island)

Anyone who likes a heavy dose of history while on holiday should reserve a regal Chanler at Cliff Walk room in Rhode Island, where heritage and luxurious modern lifestyles gloriously collide. The Chanler was originally a mansion built in 1873, though it has been used as a summer home, girls’ school, Navy accommodation and museum over the years. However, it has been given a new lease of life as The...

The Pitcher Inn
Hotel

The Pitcher Inn

USA
New England
Stowe & Woodstock (Vermont)

The Pitcher Inn is a reassuring unusual boutique hotel in Warren, Vermont, one that is full of surprises, loaded with character and not short of luxurious touches either. Housed in a building once used to host travellers during the American civil war, there is a historic theme here which runs through the very DNA of the building, something that is easily observed as soon as you arrive through the ...

The Ultimate Luxury New England Road Trip
Itinerary

The Ultimate Luxury New England Road Trip

USA
New England
Boston
+1 others
10 nights from £8,635 per person
Itinerary Highlights
  • Stay in some of New England's finest luxury hotels including a regal stay 19th century luxury mansion, The Wheatleigh and luxury boutique retreat, Twin Farms
  • Take a fun and exciting tour of Harvard with one of its students and learn about the history, architecture and student life of one of the world's most famous universities
  • The Breakers is one of New England's most famous mansions from the gilded age, located right on the ocean, here you will take a private guided tour
  • Take a private tour through impressive building 6 of Massachusetts Museum of Contemporary Art
Twin Farms
Hotel

Twin Farms

USA
New England
Stowe & Woodstock (Vermont)

Surrounded by thick forest that changes its colour throughout the year, before being blanketed in snow come winter, Twin Farms is a postcard-worthy boutique escape that has so much more to it than at first meets the eye. Take a quick look at this luxury Vermont property and you may think it’s simply a cute, rural farmhouse-style property, situated beside a picturesque pond with only forest for com...

Cliff House
Hotel

Cliff House

USA
New England
Maine Coast (Maine)

Sit back, relax, and enjoy the sea views at Cliff House, a breezy beach hotel in Maine that boasts a perfectly placed alfresco patio and two outdoor swimming pools overlooking the ocean. Well located and well equipped, Cliff House certainly has a lot to offer from its coastal perch. The look of the hotel inside is that of a sophisticated, elegant beach shack, so the floors are lined with pale wood...

Our World, Your Way

Trust &
Heritage

One of the most trusted names in luxury travel

Over 40 years’ experience in worldwide holidays

Fully bonded and protected

True
Travel Experts

We use our first-hand expertise to create a bespoke holiday

We’ve spent years establishing industry-leading contacts

Insider knowledge: our team travel to all our destinations

For Us,
It's Personal

We get to know you personally, so your trip is perfect for you

You’ll be looked after by your own personal Travel Specialist

From meet & greets to private transfers – we’ll make it happen

On hand when
you need us

24/7 assistance throughout your holiday

Our travel experts take care of you every step of the way

Our dedicated concierge team will take care of all the details

Your bookings are protected by our travel guarantee
Read More