Middleboro, MA

  • Overview
  • Performance
  • Listings
  • Buy Box

Key Performance Metrics

Market snapshot

Performance indicators for the Middleboro short-term rental market based on reliable data.

Listings

5 / 24

Reliable / Active

Revenue

$49,181

Middle-Earners Revenue

Occupancy

42%

Middle-Earners Occupancy

Top Earners

$64,013

Top-Earners Revenue

Middleboro

Market Revenue Seasonality

Top Listings

Highest revenue

The highest-performing listings in Middleboro.

Loading top listings...

C

Challenging to Investors

Middleboro Regulations

STRs are not explicitly permitted by zoning (only not prohibited), and investors must verify city licensing and tax compliance; basic business registration and safety compliance are manageable but introduce uncertainty and overhead. The absence of clear STR-specific rules and potential local taxes create compliance risk and operational friction, making the market challenging rather than welcoming.

View Middleboro Regulations →

Local STR Agent

STR specialist · Middleboro, MA

Trusted Expert
Get Expert Help In Middleboro
Free consultation Response within 24h

About Middleboro

Middleboro (also spelled Middleborough) is a town of roughly 24,000 residents in Plymouth County, in southeastern Massachusetts. It carries a small-town New England character, with quiet residential streets, working cranberry bogs, and stretches of woods and river that hint at its long history as one of the older communities in the region. The town is perhaps best known as a waypoint on the route toward Cape Cod and for its deep roots in the cranberry industry, with the Ocean Spray cooperative long associated with the area. It sits about forty miles south of Boston and roughly thirty-five miles southeast of Providence, making it a convenient crossroads between major New England population centers and the South Shore beaches.

Just to the south of town lies Myles Standish State Forest, one of the largest state forests in Massachusetts at more than twelve thousand acres. It offers miles of marked hiking and biking trails, ponds for fishing and swimming, and campgrounds, all within about a ten- to fifteen-minute drive of the town center. Visitors can spend a day wandering pine and oak woods, paddling on College Pond, or spotting wildlife in the sandy glacial terrain that characterizes the region.

A short drive north brings travelers to Plymouth, the celebrated "Pilgrim" town, roughly twenty minutes from Middleboro. The waterfront area features Plymouth Rock, the Mayflower II replica, and the living-history sites along the coast. The town's premier museum complex, Plimoth Patuxet Museums, presents reconstructed Wampanoag homes and the 1627 English village, along with a working gristmill and craft demonstrations. Plymouth Harbor, the Pilgrim Monument, and the downtown's cobbled streets make for an easy and absorbing day trip from a Middleboro base.

To the east, Middleboro serves as a practical gateway to Cape Cod. The Sagamore and Bourne bridges, where the Cape officially begins, are only about thirty to forty minutes away depending on traffic, and Routes 44 and 495 meet nearby to channel visitors toward the canal and the beaches, towns, and nature preserves of the Cape. A day trip to Cape Cod Cod, including a stop at the Cape Cod Canal, the beaches of Dennis or Sandwich, or the Cape Cod National Seashore further out, becomes highly feasible for guests staying in Middleboro.

Middleboro makes a compelling base for short-term rentals because it offers the tranquility of a New England small town with genuinely quick access to some of Massachusetts' biggest draws. Guests can return from a busy day on Cape Cod or in Plymouth to a quieter, more affordable setting, with local touches like the Nemasket River, neighborhood conservation trails, and seasonal cranberry bogs providing their own quieter rewards. For travelers who want variety without Cape Cod summer prices, the town offers a balanced and appealing alternative.

startup landing logo

Copyright © 2026 HomeRun Analytics, Inc

Explore

HomeCountry ExplorerProperty Analyzer

Resources

Market ComparatorRegulationsBlog

Trusted by STR investors in 50+ U.S. states

Built by investors, for investors

STRProfitMap® is a registered trademark of HomeRun Analytics, Inc