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
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Where to go in New England

Total results: 40
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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

Occupying a fantastic location in Boston’s Copley Square, the Fairmont Copley Plaza is comprised of 383 beautifully decorated rooms and suites, restaurant and a 3000 square foot rooftop health club. The Fairmont Copley Plaza is located within walking distance of the shopping districts of Newbury Street and the Prudential Centre as well as nearby to the Boston Common and stylish Beacon Hill area. ...

Formerly Boston’s Police Headquarters and The Back Bay Hotel, Loews Boston is a wonderful hotel for your time in Boston, situated between the South End, Theatre District and Back Bay areas. There are a collection of 222 smart guest rooms and suites decorated with a modern palette of greys, blues and neutrals and with a mix of historic charm. If you like to keep up with your fitness regime while...

XV Beacon
Hotel

XV Beacon

USA
New England
Boston

Situated on the crest of Beacon Hill in central Boston, the luxury boutique Fifteen Beacon Hotel is a 1903 landmark neoclassical building. During the restoration of the building, many of its architectural elements were retained including the original cage elevator. XV Beacon Hotel combines contemporary decor with classical and historical elements. Original artwork from some of the US's most re...

Ocean Edge Resort & Golf Club
Hotel

Ocean Edge Resort & Golf Club

USA
New England
Cape Cod & The Islands (Massachusetts)

The resort is set on the ocean edge overlooking Cape Cod Bay, only 20-minutes’ drive to Chatham and 40-minutes’ drive to Provincetown. The Mansion is home to 90 elegant rooms and two to three-bedroom Presidential Bay accommodations. Whilst staying here enjoy exclusive access to Bay Pines Private Beach (not accessible by The Villages’ guests and public). In the Mansion, there are outdoor and i...

The Cottages & Loft
Hotel

The Cottages & Loft

USA
New England
Cape Cod & The Islands (Massachusetts)

Perched on the waterfront of Nantucket Harbor overlooking the sea and boats are a collection of 29 Studios, one, two and three-Bedroom Cottages and Lofts. These lovely accommodations evoke classic New England seaside charm, each is furnished in a modern coastal-style and feature fully equipped kitchen, some offer outdoor decks. From your cottage or loft, it’s only a short walk into town or take th...

White Elephant Village, Nantucket
Hotel

White Elephant Village, Nantucket

USA
New England
Cape Cod & The Islands (Massachusetts)

Situated a short walk away from downtown and the White Elephant Hotel in Nantucket, the White Elephant Village is home to a 20 room and suite Inn and 25 one, two and three-bedroom Residences in a village garden setting. The spacious residences are particularly popular with families or groups of friends, they are furnished with kitchens and a living room with gas fireplace. The upscale Rooms and Su...

White Elephant Hotel, Nantucket
Hotel

White Elephant Hotel, Nantucket

USA
New England
Cape Cod & The Islands (Massachusetts)

Situated on the waterfront in the heart of Nantucket, is the historic and treasured White Elephant Hotel, overlooking the charming harbour and only minutes from the boutiques, restaurants and art galleries. Furnished with 54 rooms, 11 garden cottages and a loft accommodation, décor is elegant yet understated. Enjoy complimentary morning coffee and pastries, afternoon port and cheese, beach and fer...

The Wauwinet, Nantucket
Hotel

The Wauwinet, Nantucket

USA
New England
Cape Cod & The Islands (Massachusetts)

Occupying a unique location on the North East coast of Nantucket, the luxury seaside retreat The Wauwinet sits between two beaches, one facing the Atlantic Ocean and the other, Nantucket Bay. This quintessentially New England property is the only Relais & Chateaux Hotel on the island and offers impeccable service, exquisite accommodation award-winning dining. The property is set away from the cent...

Harbor View Hotel, Martha's Vineyard
Hotel

Harbor View Hotel, Martha's Vineyard

USA
New England
Cape Cod & The Islands (Massachusetts)

Situated in Edgartown in Martha’s Vineyard, the year round Harbor View Hotel is a majestic and landmark property overlooking the ocean. Looking out onto the Edgartown Lighthouse, Harbor and Chappaquiddick Island, this glorious hotel has welcomed guests since 1891. There are 114 elegant rooms spread throughout the hotel, Governor Mayhew Building and Cottages. The Harbor View is surrounded by histor...

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