4287+ Vacation Rentals & Holiday Homes in Middlesex County |
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Middlesex County Accommodations - Hotels & Rentals

About Middlesex County Vacation Rentals

Discover More than 4287 Incredible Getaway Rentals Available in Middlesex County. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Middlesex County.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Middlesex County, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Middlesex County. The Average Size of Places to Stay Near Middlesex County is 1181.6 ft², with Prices Averaging US $609 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Middlesex County. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Middlesex County

Type Count
Vacation Homes 1468
Villas 1193
Holiday Apartments 1183
Cottages 45

Use these Quick Filters to Find a Vacation Rental in Middlesex County

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Middlesex County with Online Reservations.

Activities Middlesex CountyGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World Middlesex CountyGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Dunn's River Falls
Dolphin Cove
Mystic Mountain
Jamaica Beaches
Green Grotto Caves
Hellshire Beach
Mahogany Beach
Turtle River Park
Ocho Rios Fort
Runaway Bay Beach
Golf Club at Jewel Runaway Bay
Fern Gully
Mega Mart
Shaw Park Gardens
Puerto Seco Beach Park
Ocho Rios Clock Tower
Cool Blue Hole
Maima Seville Great House & Heritage Park
Fort Clarence Beach
Ocho Rios Baptist Church

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Jamaica 8,240 Properties
North Coast 4,628 Properties
Saint Ann 1,739 Properties
Ocho Rios 1,459 Properties
Ocho Rios 948 Properties
Clarendon 686 Properties
Saint Catherine 661 Properties
Thompson Town 661 Properties
Morgans Pass 624 Properties
Saint Mary 398 Properties
Portmore 314 Properties
St. Ann's Bay 300 Properties

Frequently Asked Questions About Middlesex County?

What are the top hotels, lake houses & vacation rentals in Middlesex County?

We provide an array of great vacation destinations in Middlesex County. If you are looking to stay in or around the Middlesex County area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Middlesex County:

How many Hotels & Vacation Rentals have private pools in Middlesex County?

We have 687 Hotels & Vacation Rentals featuring a private pool in and near Middlesex County. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Middlesex County is best for families?

Searching for a family-friendly getaway in Middlesex County? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Middlesex County?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 4287 in the Middlesex County area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Middlesex County.

Nearby Neighborhood (13) 
Neighborhood Property Count
Caribbean Estates Vacation Rentals in Middlesex County, JM 48
Mammee Bay Estates Vacation Rentals in Middlesex County, JM 34
River Oaks Vacation Rentals in Middlesex County, JM 1287
Spanish Town Zone Vacation Rentals in Middlesex County, JM 121
Great Pond Vacation Rentals in Middlesex County, JM 1143
Crystal Cove Vacation Rentals in Middlesex County, JM 1209
Caribbean Park Vacation Rentals in Middlesex County, JM 427
Bridgeport Vacation Rentals in Middlesex County, JM 326
New Buckfield Vacation Rentals in Middlesex County, JM 1123
Greenwich Estate Vacation Rentals in Middlesex County, JM 471
West Cumberland Vacation Rentals in Middlesex County, JM 327
Horizon Park Vacation Rentals in Middlesex County, JM 114
Cave Hill Estate Vacation Rentals in Middlesex County, JM 41

People Also Ask

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