Middlesex County Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SAR 5,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in Middlesex County

A forested landscape with a winding dirt road and power lines.

Middletown

Middletown
A steel bridge with a truss design spanning over a calm river, surrounded by lush greenery.

Cromwell

Cromwell
A quaint white building with a dark shingled roof, a flag, and a sign reading "Toys Ahoy".

Essex

Essex
A river with a large bridge and a small boat on the shore.

Portland

Portland

Middlesex County Hotel Deals

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Fully refundable
SAR 427
SAR 491 total
13 Aug - 14 Aug
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT
SAR 944
SAR 1,150 total
2 Sep - 3 Sep
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Very clean room, some hidden costs added during check in. Resort fee tax and town or state"

Reviewed on 3 August 2026

Water's Edge Resort & Spa
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

298 E Haddam Moodus Rd East Haddam CT
SAR 541
SAR 967 total
7 Sep - 8 Sep
includes taxes & fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
See all 3,476 properties in Middlesex County
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Middlesex County attractions

A steam locomotive with the number 40 on its front, traveling on a railway track.
Photo by Bill Dillard

Essex Steam Train

8.4/10 (165 reviews)
You can spend time browsing the exhibits at Essex Steam Train during your travels in Essex Village. While you're in the area, stroll along the beautiful beaches.
See properties
A suspension bridge over a body of water, a large white building with a tower, and a forested hill in the background.

Goodspeed Opera House

9.0/10 (18 reviews)
You can make plans for a show at Goodspeed Opera House during your stay in East Haddam. Wander the riverfront and beaches in the area.
See properties
A wooden boardwalk leading to a beach at sunset.

Harvey's Beach

8.8/10 (93 reviews)
If a restful vacation is part of your travel plans, Harvey's Beach might be the perfect place to seek out during your trip to Old Saybrook. Visit the shops and spas in this relaxing area.
See properties
A large white building with columns and a central staircase.

Wadsworth Mansion

Learn about the local history of Middletown when you take a trip to Wadsworth Mansion. Experience the area's entertainment venues and festivals.
See properties

Wesleyan University

8.6/10 (189 reviews)
Enjoy the collegiate vibe when you visit Wesleyan University, during your travels in Middletown. Experience the area's festivals or attend a sporting event.
See properties

Clinton Crossing Premium Outlets

8.6/10 (135 reviews)
You can find the perfect gifts to bring home at Clinton Crossing Premium Outlets during your stay in Clinton. While you're in the area, stroll along the beautiful beaches.
See properties

TPC River Highlands

6.8/10 (22 reviews)
Enjoy a round of golf in Cromwell at TPC River Highlands. While in this family-friendly area, you can savor the top-notch restaurants.
See properties

Westbrook Town Beach

8.8/10 (36 reviews)
Why not spend a lazy afternoon at Westbrook Town Beach during your trip to Westbrook?
See properties